Carbohydrate synthesis and biosynthesis technologies for cracking of the glycan code: Recent advances

Biotechnology Advances - Tập 31 - Trang 17-37 - 2013
Hynek Mrázek, Lenka Weignerová, Pavla Bojarová, Petr Novák, Ondřej Vaněk, Karel Bezouška

Tài liệu tham khảo

Abe, 2009, Development of valuable yeast strains using a novel mutagenesis technique for the effective production of therapeutic glycoproteins, Glycobiology, 19, 428, 10.1093/glycob/cwn157 Adamson, 2006, Infrared multiphoton dissociation and electron capture dissociation of high-mannose type glycopeptides, J Proteome Res, 5, 493, 10.1021/pr0504081 Aricescu, 2007, Structure of a tyrosine phosphatase adhesive interaction reveals a spacer-clamp mechanism, Science, 317, 1217, 10.1126/science.1144646 Arnold, 2007, The impact of glycosylation on the biological function and structure of human immunoglobulins, Annu Rev Immunol, 25, 21, 10.1146/annurev.immunol.25.022106.141702 Aumiller, 2003, A transgenic lepidopteran insect cell line engineered to produce CMP-sialic acid and sialoglycoproteins, Glycobiology, 13, 497, 10.1093/glycob/cwg051 Aumiller, 2012, A new glycoengineered insect cell line with an inducibly mammalianized protein N-glycosylation pathway, Glycobiology, 22, 417, 10.1093/glycob/cwr160 Barnard, 2010, High-throughput screening and selection of yeast cell lines expressing monoclonal antibodies, J Ind Microbiol Biotechnol, 37, 961, 10.1007/s10295-010-0746-1 Beck, 2008, Trends in glycosylation, glycoanalysis and glycoengineering of therapeutic antibodies and Fc-fusion proteins, Curr Pharm Biotechnol, 9, 482, 10.2174/138920108786786411 Bejugam, 2004, An efficient synthetic route to glycoamino acid building blocks for glycopeptide synthesis, Org Lett, 6, 4001, 10.1021/ol048342n Bobrowicz, 2004, Engineering of an artificial glycosylation pathway blocked in core oligosaccharide assembly in the yeast Pichia pastoris: production of complex humanized glycoproteins with terminal galactose, Glycobiology, 14, 757, 10.1093/glycob/cwh104 Boeggeman, 2009, Site specific conjugation of fluoroprobes to the remodeled Fc N-glycans of monoclonal antibodies using mutant glycosyltransferases: application for cell surface antigen detection, Bioconjug Chem, 20, 1228, 10.1021/bc900103p Bojarová, 2009, Glycosidases: a key to tailored carbohydrates, Trends Biotechnol, 7, 199, 10.1016/j.tibtech.2008.12.003 Bojarová, 2007, Glycosyl azides—an alternative way to disaccharides, Adv Synth Catal, 349, 1514, 10.1002/adsc.200700028 Bojarová, 2008, N-acetylhexosamine triad in one molecule: chemoenzymatic introduction of 2-acetamido-2-deoxy-β-d-galactopyranosyluronic acid residue into a complex oligosaccharide, J Mol Catal B Enzym, 50, 69, 10.1016/j.molcatb.2007.09.002 Bojarová, 2009, Synthesis of LacdiNAc-terminated glycoconjugates by mutant galactosyltransferase—a way to new glycodrugs and materials, Glycobiology, 19, 509, 10.1093/glycob/cwp010 Bojarová, 2011, Charged hexosaminides as new substrates for β-N-acetylhexosaminidase-catalyzed synthesis of immunomodulatory disaccharides, Adv Synth Catal, 353, 2409, 10.1002/adsc.201100371 Bowden, 2008, Structural basis of Nipah and Hendra virus attachment to their cell-surface receptor ephrin-B2, Nat Struct Mol Biol, 15, 567, 10.1038/nsmb.1435 Brocke, 2004, Synthetic tumor-associated glycopeptide antigens from the tandem repeat sequence of the epithelial mucin MUC4, Synthesis, 4, 525 Callewaert, 2001, Use of HDEL-tagged Trichoderma reesei mannosyl oligosaccharide 1,2-α-d-mannosidase for N-glycan engineering in Pichia pastoris, FEBS Lett, 503, 173, 10.1016/S0014-5793(01)02676-X Carr, 1986, Carbohydrate mapping by mass spectrometry: a novel method for identifying attachment sites of Asn-linked sugars in glycoproteins, Anal Biochem, 157, 396, 10.1016/0003-2697(86)90643-3 Castilho, 2011, N-glycosylation engineering of plants for the biosynthesis of glycoproteins with bisected and branched complex N-glycans, Glycobiology, 21, 813, 10.1093/glycob/cwr009 Chang, 2007, Glycoprotein structural genomics: solving the glycosylation problem, Structure, 15, 267, 10.1016/j.str.2007.01.011 Cheng, 2008, Multifunctionality of Campylobacter jejuni sialyltransferase CstII: characterization of GD3/GT3 oligosaccharide synthase, GD3 oligosaccharide sialidase, and trans-sialidase activities, Glycobiology, 18, 686, 10.1093/glycob/cwn047 Cheng, 2010, Trans-sialidase activity of Photobacterium damsela α-2,6-sialyltransferase and its application in the synthesis of sialosides, Glycobiology, 20, 260, 10.1093/glycob/cwp172 Chiba, 1998, Production of human compatible high mannose-type (Man5GlcNAc2) sugar chains in Saccharomyces cerevisiae, J Biol Chem, 273, 26298, 10.1074/jbc.273.41.26298 Chigira, 2008, Engineering of a mammalian O-glycosylation pathway in the yeast Saccharomyces cerevisiae: production of O-fucosylated epidermal growth factor domains, Glycobiology, 18, 303, 10.1093/glycob/cwn008 Choi, 2008, Recombinant human lactoferrin expressed in glycoengineered Pichia pastoris: effect of terminal N-acetylneuraminic acid on in vitro secondary humoral immune response, Glycoconj J, 25, 581, 10.1007/s10719-008-9123-y Chokhawala, 2008, Combinatorial chemoenzymatic synthesis and high-throughput screening of sialosides, ACS Chem Biol, 3, 567, 10.1021/cb800127n Cobucci-Ponzano, 2011, Glycosynthases in biocatalysis, Adv Synth Catal, 353, 2284, 10.1002/adsc.201100461 Coles, 2011, Proteoglycan-specific molecular switch for RPTPσ clustering and neuronal extension, Science, 332, 484, 10.1126/science.1200840 Cox, 2006, Glycan optimization of a human monoclonal antibody in the aquatic plant Lemna minor, Nat Biotechnol, 24, 1591, 10.1038/nbt1260 Crich, 2002, Chemistry of glycosyl triflates: synthesis of ß-mannopyranosides, J Carbohydr Chem, 21, 667, 10.1081/CAR-120016486 Crich, 2005, Improved synthesis of 1-benzenesulfinyl piperidine and analogs for the activation of thioglycosides in conjunction with trifluoromethanesulfonic anhydride, J Carbohydr Chem, 24, 415, 10.1081/CAR-200066978 Crispin, 2009, A human embryonic kidney 293T cell line mutated at the Golgi α-mannosidase II locus, J Biol Chem, 284, 21684, 10.1074/jbc.M109.006254 Cumpstey, 2008, Intramolecular aglycon delivery, Carbohydr Res, 343, 1553, 10.1016/j.carres.2008.04.031 Dalpathado, 1986, Carbohydrate mapping by mass spectrometry: a novel method for identifying attachment sites of Asn-linked sugars in glycoproteins, Anal Biochem, 157, 396, 10.1016/0003-2697(86)90643-3 Damiani, 2009, Stable expression of a human-like sialylated recombinant thyrotropin in a Chinese hamster ovary cell line expressing alpha2,6-sialyltransferase, Protein Expr Purif, 67, 7, 10.1016/j.pep.2009.04.005 Davidson, 2004, Functional analysis of the alg3 gene encoding the Dol-P-Man: Man5GlcNAc2-PP-Dol mannosyltransferase enzyme of P. pastoris, Glycobiology, 14, 399, 10.1093/glycob/cwh023 Davis, 1993, Expression of soluble recombinant glycoproteins with predefined glycosylation: application to the crystallization of the T-cell glycoprotein CD2, Protein Eng, 6, 229, 10.1093/protein/6.2.229 Davis, 2000, Rituximab anti-CD20 monoclonal antibody therapy in non-Hodgkin's lymphoma: safety and efficacy of re-treatment, J Clin Oncol, 18, 3135, 10.1200/JCO.2000.18.17.3135 Demchenko, 2005, Strategic approach to the chemical oligosaccharide synthesis, Lett Org Chem, 2, 580, 10.2174/157017805774296975 Demchenko, 2003, S-Benzoxazolyl (SBox) glycosides as novel, versatile glycosyl donors for stereoselective 1,2-cis glycosylation, Org Lett, 5, 455, 10.1021/ol0273452 Drickamer, 1998, Evolving views of protein glycosylation, Trends Biochem Sci, 23, 321, 10.1016/S0968-0004(98)01246-8 Drouillard, 2010, Efficient synthesis of 6′-sialylactose, 6,6′-disialyllactose, and 6′-KDOlactose by metabolically engineered E. coli expressing a multifunctional sialyltransferase from Photobacterium sp. JTISH-224, Carbohydr Res, 345, 1394, 10.1016/j.carres.2010.02.018 Dudkin, 2004, Toward fully synthetic carbohydrate-based HIV antigen design: on the critical role of bivalency, J Am Chem Soc, 126, 9560, 10.1021/ja047720g Durocher, 2009, Expression systems for therapeutic glycoprotein production, Curr Opin Biotechnol, 20, 700, 10.1016/j.copbio.2009.10.008 Dwek, 1996, Toward understanding the function of sugars, Chem Rev, 96, 683, 10.1021/cr940283b Dziadek, 2004, Biomimetic synthesis of the tumor-associated (2,3)-sialyl-T antigen and its incorporation into glycopeptide antigens from the mucins MUC1 and MUC4, Chem Eur J, 10, 4150, 10.1002/chem.200400228 Ecker, 2003, O-mannosylation precedes and potentially controls the N-glycosylation of a yeast cell wall glycoprotein, EMBO Rep, 4, 628, 10.1038/sj.embor.embor864 Edelman, 1997, Obtaining a functional recombinant anti-rhesus (D) antibody using the baculovirus–insect cell expression system, Immunology, 91, 13, 10.1046/j.1365-2567.1997.00219.x Egrie, 2003, Darbepoetin alfa has a longer circulating half-life and greater in vivo potency than recombinant human erythropoietin, Exp Hematol, 31, 290, 10.1016/S0301-472X(03)00006-7 El Ashry, 2005, Strategies of synthetic methodologies for constructing β-mannosidic linkage, Curr Org Synth, 2, 175, 10.2174/1570179053545378 Elbein, 1990, Kifunensine, a potent inhibitor of the glycoprotein processing mannosidase I, J Biol Chem, 265, 15599, 10.1016/S0021-9258(18)55439-9 El-Boubbou, 2010, Magnetic glyconanoparticles: a tool to detect, differentiate, and unlock the glycocodes of cancer via magnetic resonance imaging, J Am Chem Soc, 132, 4490, 10.1021/ja100455c Eller, 2007, Synthesis of pentaantennary N-glycans with bisecting GlcNAc and core fucose, Angew Chem Int Ed, 46, 4173, 10.1002/anie.200604788 Fascione, 2009, Stereoselective glycosylation using oxathiane glycosyl donors, Chem Commun, 39, 5841, 10.1039/b913308a Fascione, 2012, Do glycosyl sulfonium ions engage in neighbouring-group participation? A study of oxathiane glycosyl donors and the basis for their stereoselectivity fascione, Chemistry, 18, 321, 10.1002/chem.201101889 Feizi, 2004, Oligosaccharide microarrays to decipher the glyco code, Nat Rev Mol Cell Biol, 5, 582, 10.1038/nrm1428 Fenn, 1989, Electrospray ionization for mass spectrometry of large biomolecules, Science, 246, 64, 10.1126/science.2675315 Ferrara, 2006, Modulation of therapeutic antibody effector functions by glycosylation engineering: influence of Golgi enzyme localization domain and co-expression of heterologous beta-1, 4-N-acetylglucosaminyltransferase III and Golgi alphamannosidase II, Biotechnol Bioeng, 93, 851, 10.1002/bit.20777 Fialová, 2004, Hydrolytic and transglycosylation reactions of N-acyl modified substrates catalysed by β-N-acetylhexosaminidases, Tetrahedron, 60, 693, 10.1016/j.tet.2003.10.111 Fialová, 2005, Combined application of galactose oxidase and β-N-acetylhexosaminidase in the synthesis of complex immunoactive N-acetyl-d-galactosaminides, Adv Synth Catal, 347, 997, 10.1002/adsc.200505041 Fraser-Reid, 2006, Synthesis of a 28-mer oligosaccharide core of mycobacterial lipoarabinomannan (LAM) requires only two n-pentenyl ortho-ester progenitors, Tetrahedron: Asymmetry, 17, 2449, 10.1016/j.tetasy.2006.09.008 Fujita, 2001, A novel disaccharide substrate having 1,2-oxazoline moiety for detection of transglycosylating activity of endoglycosidases, Biochim Biophys Acta, 1528, 9, 10.1016/S0304-4165(01)00164-7 Gagneux, 1999, Evolutionary considerations in relating oligosaccharide diversity to biological function, Glycobiology, 9, 747, 10.1093/glycob/9.8.747 Gantt, 2008, Probing the aglycon promiscuity of an engineered glycosyltransferase, Angew Chem Int Ed, 47, 8889, 10.1002/anie.200803508 Garegg, 1997, Thioglycosides as glycosyl donors in oligosaccharide synthesis, Adv Carbohydr Chem Biochem, 52, 179, 10.1016/S0065-2318(08)60091-8 Gerardy-Schahn, 2001, Nucleotide sugar transporters: biological and functional aspects, Biochimie, 83, 775, 10.1016/S0300-9084(01)01322-0 Gerngross, 2004, Advances in the production of human therapeutic proteins in yeasts and filamentous fungi, Nat Biotechnol, 22, 1409, 10.1038/nbt1028 Ghosh, 2010, Concise synthesis of a hexasaccharide present in the cell wall lipopolysaccharide of Azospirillum lipoferum Sp59b, Tetrahedron: Asymmetry, 21, 725, 10.1016/j.tetasy.2010.03.042 Goh, 2010, RCA-I-resistant CHO mutant cells have dysfunctional GnT I and expression of normal GnT I in these mutants enhances sialylation of recombinant erythropoietin, Metab Eng, 12, 360, 10.1016/j.ymben.2010.03.002 Goto, 2001, UDP sugar transporter implicated in glycosylation and processing of Notch, Nat Cell Biol, 3, 816, 10.1038/ncb0901-816 Hamilton, 2003, Production of complex human glycoproteins in yeast, Science, 301, 1244, 10.1126/science.1088166 Hamilton, 2006, Humanization of yeast to produce complex terminally sialylated glycoproteins, Science, 313, 1441, 10.1126/science.1130256 Harrison, 2006, Protein N-glycosylation in the baculovirus-insect cell expression system and engineering of insect cells to produce “mammalianized” recombinant glycoprotein, Adv Virus Res, 68, 159, 10.1016/S0065-3527(06)68005-6 He, 2004, Stereoselective N-glycosylation by Staudinger ligation, Org Lett, 6, 4479, 10.1021/ol048271s Hecht, 2009, Recent advances in carbohydrate-based vaccines, Curr Opin Chem Biol, 13, 354, 10.1016/j.cbpa.2009.05.127 Helenius, 2002, Translocation of lipid-linked oligosaccharides across the ER membrane requires Rft1 protein, Nature, 415, 447, 10.1038/415447a Hewitt, 2002, Rapid synthesis of a glycosylphosphatidylinositol-based malaria vaccine using automated solid-phase oligosaccharide synthesis, J Am Chem Soc, 124, 13434, 10.1021/ja027538k Hirayama, 1998, Complete and rapid peptide and glycopeptide mapping of mouse monoclonal antibody by LC/MS/MS using ion trap mass spectrometry, Anal Chem, 70, 2718, 10.1021/ac9712153 Hirschberg, 1998, Transporters nucleotide sugars, ATP, and nucleotide sulfate in the endoplasmic reticulum and Golgi apparatus, Annu Rev Biochem, 67, 49, 10.1146/annurev.biochem.67.1.49 Hoffmann, 1998, A structural role for glycosylation: lessons from the hp model, Fold Des, 3, 337, 10.1016/S1359-0278(98)00046-7 Holm, 2005, Identification of the minimal glycopeptide core recognized by T cells in a model for rheumatoid arthritis, Bioorg Med Chem, 13, 473, 10.1016/j.bmc.2004.10.011 Huang, 2004, Iterative one-pot synthesis of oligosaccharides, Angew Chem Int Ed, 43, 5221, 10.1002/anie.200460176 Huang, 2009, Glycosynthases enable a highly efficient chemoenzymatic synthesis of N-glycoproteins carrying intact natural N-glycans, J Am Chem Soc, 131, 2214, 10.1021/ja8074677 Hüssy, 1997, Evaluation of hepatitis C virus envelope proteins expressed in E. coli and insect cells for use as tools for antibody screening, J Hepatol, 26, 1179, 10.1016/S0168-8278(97)80450-3 Hutchinson, 2010, Redesign of polyene macrolide glycosylation: engineered biosynthesis of 19-(O)-perosaminyl-amphoteronolide B, Chem Biol, 17, 174, 10.1016/j.chembiol.2010.01.007 Idiris, 2010, Engineering of protein secretion in yeast: strategies and impact on protein production, Appl Microbiol Biotechnol, 86, 403, 10.1007/s00253-010-2447-0 Iida, 2006, Nonfucosylated therapeutic IgG1 antibody can evade the inhibitory effect of serum immunoglobulin G on antibodydependent cellular cytotoxicity through its high binding to FcgammaRIIIa, Clin Cancer Res, 12, 2879, 10.1158/1078-0432.CCR-05-2619 Ito, 1996, Orthogonal glycosylation strategy for rapid assembly of oligosaccharides on a polymer support, Angew Chem Int Ed, 35, 2510, 10.1002/anie.199625101 Jacobs, 2009, Engineering complex-type N-glycosylation in Pichia pastoris using GlycoSwitch technology, Nat Protoc, 4, 58, 10.1038/nprot.2008.213 Jalsa, 2009, A unique approach to the synthesis of a dengue vaccine and the novel tetrasaccharide that results, Tetrahedron: Asymmetry, 20, 867, 10.1016/j.tetasy.2009.02.024 Jayapal, 2007, Recombinant protein therapeutics from CHO cells—20years and counting, Chem Eng Prog, 103, 40 Jiang, 2010, A high-throughput purification of monoclonal antibodies from glycoengineered Pichia pastoris, Protein Expr Purif, 74, 9, 10.1016/j.pep.2010.04.016 Jiang, 2011, Purification process development of a recombinant monoclonal antibody expressed in glycoengineered Pichia pastoris, Protein Expr Purif, 76, 7, 10.1016/j.pep.2010.11.004 Jones, 2009, Reproductive glycogenetics—a critical factor in pregnancy success, Placenta, 30, 216, 10.1016/j.placenta.2008.12.005 Jones, 2011, Cracking the glycan sequence code, Nat Chem Biol, 7, 758, 10.1038/nchembio.696 Kaba, 2003, Baculovirus surface display of Theileria parva p67 antigen preserves the conformation of sporozoite-neutralizing epitopes, Protein Eng, 16, 73, 10.1093/proeng/gzg004 Kainz, 2008, N-glycan modification in Aspergillus species, Appl Environ Microbiol, 74, 1076, 10.1128/AEM.01058-07 Kaltgrad, 2008, Onvirus construction of polyvalent glycan ligands for cell-surface receptors, J Am Chem Soc, 130, 4578, 10.1021/ja077801n Karg, 2009, The production of biopharmaceuticals in plant systems, Biotechnol Adv, 27, 879, 10.1016/j.biotechadv.2009.07.002 Kasajima, 2006, In vivo expression of UDP-N-acetylglucosamine: α-1,3-d-mannoside β-1,2-N-acetylglucosaminyltransferase I (GnT-1) in Aspergillus oryzae and effects on the sugar chain of alphaamylase, Biosci Biotechnol Biochem, 70, 2662, 10.1271/bbb.60265 Kelleher, 1999, Top down versus bottom up protein characterization by tandem high-resolution mass spectrometry, J Am Chem Soc, 121, 806, 10.1021/ja973655h Kim, 2004, Production of antithrombotic hirudin in GAL1-disrupted Saccharomyces cerevisiae, Appl Microbiol Biotechnol, 65, 259, 10.1007/s00253-004-1598-2 Kim, 2005, A general strategy for stereoselective glycosylations, J Am Chem Soc, 127, 12090, 10.1021/ja052548h Kim, 2006, Functional characterization of the Hansenula polymorpha hoc1, och1, and ocr1 genes as members of the yeast OCH1 mannosyltransferase family involved in protein glycosylation, J Biol Chem, 281, 6261, 10.1074/jbc.M508507200 Kim, 2012, CHO cells in biotechnology for production of recombinant proteins: current state and further potential, Appl Microbiol Biotechnol, 93, 917, 10.1007/s00253-011-3758-5 Koeller, 2000, Synthesis of complex carbohydrates and glycoconjugates: enzyme-based and programmable one-pot strategies, Chem Rev, 100, 4465, 10.1021/cr990297n Koenigs, 1901, Ueber einige Derivate des Traubenzuckers und der Galactose, Ber Dtsch Chem Ges, 34, 957, 10.1002/cber.190103401162 Kornfeld, 1985, Assembly of asparagine-linked oligosaccharides, Annu Rev Biochem, 54, 631, 10.1146/annurev.bi.54.070185.003215 Kovalová, 2010, Synthesis of N-acetyl-d-glucosamine based fully branched tetrasaccharide, a mimetic of the endogenous ligand for CD69, activate CD69+ killer lymphocytes upon dimerization via a hydrophobic flexible linker, J Med Chem, 53, 4050, 10.1021/jm100055b Krist, 2004, Fluorescent labelled thiourea-bridged glycodendrons, Chembiochem, 5, 445, 10.1002/cbic.200300669 Lam, 2005, Efficient synthesis of Man2, Man3, and Man5 oligosaccharides, using mannosyl iodide donors, J Org Chem, 70, 8772, 10.1021/jo051360d Lemieux, 1975, Halide ion catalyzed glycosidation reactions. Syntheses of a-linked disaccharides, J Am Chem Soc, 97, 4056, 10.1021/ja00847a032 Li, 2006, Optimization of humanized IgGs in glycoengineered Pichia pastoris, Nat Biotechnol, 24, 210, 10.1038/nbt1178 Li, 2012, Recombinant gp90 protein expressed in Pichia pastoris induces a protective immune response against reticuloendotheliosis virus in chickens, Vaccine, 30, 2273, 10.1016/j.vaccine.2012.01.075 Likhosherstov, 1986, A new simple synthesis of amino sugar β-d-glycosylamines, Carbohydr Res, 146, C1, 10.1016/0008-6215(86)85037-6 Liu, 2005, Secretory expression and characterization of a recombinant-deleted variant of human hepatocyte growth factor in Pichia pastoris, World J Gastroenterol, 11, 7097, 10.3748/wjg.v11.i45.7097 Liu, 2009, Disruption of the och1 and mnn1 genes decrease N-glycosylation on glycoprotein expressed in Kluyveromyces lactis, J Biotechnol, 143, 95, 10.1016/j.jbiotec.2009.06.016 Liu, 2011, Pharmacokinetics of IgG1 monoclonal antibodies produced in humanized Pichia pastoris with specific glycoforms: a comparative study with CHO produced materials, Biologicals, 39, 205, 10.1016/j.biologicals.2011.06.002 Liu, 2010, Chemoenzymatic design of heparan sulfate oligosaccharides, J Biol Chem, 285, 34240, 10.1074/jbc.M110.159152 Loft, 2009, Synthesis of sulfated glucosaminides for profiling substrate specificities of sulfatases and fungal β-N-acetylhexosaminidases, Chembiochem, 10, 565, 10.1002/cbic.200800656 Lopez, 2007, Investigation of the specificity of an α-l-arabinofuranosidase using C-2 and C-5 modified α-l-arabinofuranosides, Carbohydr Res, 342, 2202, 10.1016/j.carres.2007.06.001 Love, 2005, Synthesis and use of glycosyl phosphates as glycosyl donors, Org Synth, 81, 225, 10.15227/orgsyn.081.0225 Ly, 2011, The proteoglycan bikunin has a defined sequence, Nat Chem Biol, 7, 827, 10.1038/nchembio.673 Macmillan, 2004, Modular assembly of glycoproteins: towards the synthesis of GlyCAM-1 by using expressed protein ligation, Angew Chem Int Ed, 43, 1355, 10.1002/anie.200352673 Mandal, 2004, In pursuit of carbohydrate-based HIV vaccines, part 1: The total synthesis of hybrid-type gp120 fragments, Angew Chem Int Ed, 43, 2557, 10.1002/anie.200353625 Maras, 2000, Molecular cloning and enzymatic characterization of a Trichoderma reesei 1,2-α-D-mannosidase, J Biotechnol, 77, 255, 10.1016/S0168-1656(99)00222-9 Markussen, 1987, Soluble, prolonged-acting insulin derivatives. II. Degree of protraction and crystallizability of insulins substituted in positions A17, B8, B13, B27 and B30, Protein Eng, 1, 215, 10.1093/protein/1.3.215 Markussen, 1988, Soluble, prolonged-acting insulin derivatives. III. Degree of protraction, crystallizability and chemical stability of insulins substituted in positions A21, B13, B23, B27 and B30, Protein Eng, 2, 157, 10.1093/protein/2.2.157 Martínek, 2010, Glycosylation protects proteins against free radicals generated from toxic xenobiotics, Toxicol Sci, 117, 359, 10.1093/toxsci/kfq206 Measaeli, 1999, Calreticulin is essential for cardiac development, J Cell Biol, 144, 857, 10.1083/jcb.144.5.857 Mirzaei, 2009, Nonviral production of human interleukin-7 in Spodoptera frugiperda insect cells as a soluble recombinant protein, J Biomed Biotechnol, 2009, 637942, 10.1155/2009/637942 Mitra, 2006, N-linked oligosaccharides as outfitters for glycoprotein folding, form and function, Trends Biochem Sci, 31, 156, 10.1016/j.tibs.2006.01.003 Molinari, 1999, Glycoproteins form mixed disulphides with oxidoreductases during folding in living cells, Nature, 402, 90, 10.1038/47062 Mootoo, 1988, n-Pentenyl glycosides permit the chemospecific liberation of the anomeric center, J Am Chem Soc, 110, 2662, 10.1021/ja00216a057 Murrey, 2009, Identification of the plasticity-relevant fucose-a-(1–2)-galactose proteome from the mouse olfactory bulb, Biochemistry, 48, 7261, 10.1021/bi900640x Muthana, 2007, Chemoenzymatic synthesis of size-defined polysaccharides by sialyltransferase catalyzed block transfer of oligosaccharides, J Am Chem Soc, 129, 11918, 10.1021/ja075736b Muthana, 2009, Recent progress in chemical and chemoenzymatic synthesis of carbohydrates, Curr Opin Chem Biol, 13, 573, 10.1016/j.cbpa.2009.09.013 Mydock, 2008, Superarming the S-benzoxazolyl glycosyl donors by simple 2-O-benzoyl-3,4,6-tri-O-benzyl protection, Org Lett, 10, 2103, 10.1021/ol800345j Nagasu, 1992, Isolation of new temperature sensitive mutants of Saccharomyces cerevisiae deficient in mannose outer chain elongation, Yeast, 8, 535, 10.1002/yea.320080705 Nakanishi-Shindo, 1993, Structure of the N-linked oligosaccharides that show the complete loss of alpha-1,6-polymannose outer chain from och1, och1 mnn1, and och1 mnn1 alg3 mutants of Saccharomyces cerevisiae, J Biol Chem, 268, 26338, 10.1016/S0021-9258(19)74320-8 Namdjou, 2008, A β-1,4-galactosyltransferase from Helicobacter pylori is an efficient and versatile biocatalyst displaying a novel activity for thioglycoside synthesis, Chembiochem, 9, 1632, 10.1002/cbic.200700775 Nettleship, 2010, Recent advances in the production of proteins in insect and mammalian cells for structural biology, J Struct Biol, 172, 55, 10.1016/j.jsb.2010.02.006 Nifantiev, 2009 North, 2009, Mass spectrometry in the analysis of N-linked and O-linked glycans, Curr Opin Struct Biol, 19, 498, 10.1016/j.sbi.2009.05.005 Oberli, 2011, A possible oligosaccharide-conjugate vaccine candidate for Clostridium difficile is antigenic and immunogenic, Chem Biol, 18, 580, 10.1016/j.chembiol.2011.03.009 Oh, 2008, Glycoengineering of the methylotrophic yeast Hansenula polymorpha for the production of glycoproteins with trimannosyl core N-glycan by blocking core oligosaccharide assembly, Biotechnol J, 3, 659, 10.1002/biot.200700252 Onitsuka, 2012, Enhancement of sialylation on humanized IgG-like bispecific antibody by overexpression of α2,6-sialyltransferase derived from Chinese hamster ovary cells, Appl Microbiol Biotechnol, 94, 69, 10.1007/s00253-011-3814-1 Oyelaran, 2009, Glycan arrays: recent advances and future challenges, Curr Opin Chem Biol, 13, 406, 10.1016/j.cbpa.2009.06.021 Palcic, 2011, Glycosyltransferases as biocatalysts, Curr Opin Chem Biol, 15, 226, 10.1016/j.cbpa.2010.11.022 Palmacci, 2002, Oligosaccharide synthesis in solution and on solid support with glycosyl phosphates, Eur J Org Chem, 20, 595, 10.1002/1099-0690(200202)2002:4<595::AID-EJOC595>3.0.CO;2-V Panchadhayee, 2010, Synthesis of penta- and hexasaccharide fragments corresponding to the O-antigen of Escherichia coli O150, Tetrahedron: Asymmetry, 21, 2142, 10.1016/j.tetasy.2010.06.022 Parameswar, 2009, Synthesis, conjugation, and immunological evaluation of the serogroup 6 pneumococcal oligosaccharides, ChemBioChem, 10, 2893, 10.1002/cbic.200900587 Patnaik, 2006, Lectin-resistant CHO glycosylation mutants, Methods Enzymol, 416, 159, 10.1016/S0076-6879(06)16011-5 Pedersen, 2007, “Super armed” glycosyl donors: conformational arming of thioglycosides by silylation, J Am Chem Soc, 129, 9222, 10.1021/ja071955l Petitou, 2004, A synthetic antithrombin III binding pentasaccharide is now a drug! What comes next?, Angew Chem Int Ed Engl, 43, 3118, 10.1002/anie.200300640 Petrescu, 2006, Structural aspects of glycomes with a focus on N-glycosylation and glycoprotein folding, Curr Opin Struct Biol, 16, 600, 10.1016/j.sbi.2006.08.007 Phalipon, 2009, A Synthetic carbohydrate-protein conjugate vaccine vandidate against Shigella flexneri 2a infection, J Immunol, 182, 2241, 10.4049/jimmunol.0803141 Pilobello, 2007, Deciphering the glycocode: the complexity and analytical challenge of glycomics, Curr Opin Chem Biol, 11, 300, 10.1016/j.cbpa.2007.05.002 Plante, 2000, Formation of ß-glucosamine and β-mannose linkages using glycosyl phosphates, Org Lett, 2, 3841, 10.1021/ol006566+ Plante, 2001, Oligosaccharide synthesis with glycosyl phosphate and dithiophosphate triesters as glycosylating agents, J Am Chem Soc, 123, 9545, 10.1021/ja016227r Plíhal, 2004, N-glycosylated catalytic subunit meets O-glycosylated propeptide: complex protein architecture in a fungal hexosaminidase, Biochem Soc Trans, 32, 764, 10.1042/BST0320764 Pohl, 2004, Cellular addresses: step one in creating a glycocode, Chem Biol, 11, 891, 10.1016/j.chembiol.2004.07.004 Pollak, 1977, Large-scale enzymatic synthesis with cofactor regeneration - Glucose-6-phosphate, J Am Chem Soc, 99, 2366, 10.1021/ja00449a071 Pornsuriyasak, 2006, S-thiazolinyl (STaz) glycosides as versatile building blocks for convergent selective, chemoselective, and orthogonal oligosaccharide synthesis, Chem Eur J, 12, 6630, 10.1002/chem.200600262 Pospíšil, 2000, Cancer immunomodulation by carbohydrate ligands for the lymphocyte receptor NKR-P1, Int J Oncol, 16, 267 Potgieter, 2009, Production of monoclonal antibodies by glycoengineered Pichia pastoris, J Biotechnol, 139, 318, 10.1016/j.jbiotec.2008.12.015 Pourcq, 2010, Engineering of glycosylation on yeast and other fungi: current state and perspectives, Appl Microbiol Biotechnol, 87, 1617, 10.1007/s00253-010-2721-1 Pratt, 2004, Deconvoluting the functions of polypeptide α-N-acetylgalactosaminyltransferase family members by glycopeptide substrate profiling, Chem Biol, 11, 1009, 10.1016/j.chembiol.2004.05.009 Premathilake, 2011, Superarmed and superdisarmed building blocks in expeditious oligosaccharide synthesis, Top Curr Chem, 301, 189, 10.1007/128_2010_106 Price, 2010, Context-dependent effects of asparagine glycosylation on Pin WW folding kinetics and thermodynamics, J Am Chem Soc, 132, 15359, 10.1021/ja106896t Pudelko, 2010, Chemical and chemoenzymatic synthesis of glycopeptide selectin ligands containing sialyl Lewis X structures, Chembiochem, 11, 904, 10.1002/cbic.201000029 Ragupathi, 2009, Synthesis of sialyl Lewisa (sLea, CA19-9) and construction of an immunogenic sLea valine, Cancer Immunol Immunother, 58, 1397, 10.1007/s00262-008-0654-7 Rao, 2011, Expression of codon optimized major capsid protein (L1) of human papillomavirus type 16 and 18 in Pichia pastoris; purification and characterization of the virus-like particles, Vaccine, 29, 7326, 10.1016/j.vaccine.2011.07.071 Rech, 2011, Combinatorial one-pot synthesis of poly-N-acetyllactosamine oligosaccharides with Leloir-glycosyltransferases, Adv Synth Catal, 353, 2492, 10.1002/adsc.201100375 Reeves, 2002, Structure and function in rhodopsin: a tetracycline-inducible system in stable mammalian cell lines for high-level expression of opsin mutants, Proc Natl Acad Sci U S A, 99, 13413, 10.1073/pnas.212519199 Roth, 2010, Protein N-glycosylation, protein folding, and protein quality control, Mol Cell, 30, 497, 10.1007/s10059-010-0159-z Ryšlavá, 2011, Enzymatic characterization and molecular modeling of an evolutionarily interesting fungal β-N-acetylhexosaminidase, FEBS J, 278, 2469, 10.1111/j.1742-4658.2011.08173.x Saksena, 2007, Immunogens related to the synthetic tetrasaccharide side chain of the Bacillus anthracis exosporium, Bioorg Med Chem, 15, 4283, 10.1016/j.bmc.2007.03.057 Sames, 1997, Convergent total synthesis of a tumour-associated mucin motif, Nature, 389, 587, 10.1038/39292 Sato, 2004, Site-specific introduction of sialic acid into insulin, Angew Chem Int Ed, 43, 1516, 10.1002/anie.200353058 Satoh, 2006, Non-fucosylated therapeutic antibodies as next-generation therapeutic antibodies, Expert Opin Biol Ther, 6, 1161, 10.1517/14712598.6.11.1161 Sauerzapfe, 2009, Chemo-enzymatic synthesis of poly-N-acetyllactosamine (poly-LacNAc) structures and their characterization for CGL2-galectin-mediated binding of ECM glycoproteins to biomaterial surfaces, Glycoconj J, 26, 141, 10.1007/s10719-008-9172-2 Schofield, 2002, Synthetic GPI as a candidate anti-toxic vaccine in a model of malaria, Nature, 418, 785, 10.1038/nature00937 Seeberger, 2000, Solid-phase oligosaccharide synthesis and combinatorial carbohydrate libraries, Chem Rev, 100, 4349, 10.1021/cr9903104 Semeňuk, 2001, Synthesis of chitooligomer-based glycoconjugates and their binding to rat natural killer cell activation receptor NKR-P1, Glycoconj J, 18, 817, 10.1023/A:1021111703443 Shaked, 1980, Enzyme-catalyzed organic synthesis—NADH regeneration by using formate dehydrogenase, J Am Chem Soc, 102, 7104, 10.1021/ja00543a038 Shao, 2005, Solution-phase synthesis with solid-state workup of an O-glycopeptide with a cluster of cancer-related T antigens, Org Lett, 7, 3589, 10.1021/ol0514193 Sharon, 1980, Carbohydrates, Sci Am, 243, 90, 10.1038/scientificamerican1180-90 Shental-Bechor, 2008, Effect of glycosylation on protein folding: a close look at thermodynamic stabilization, Proc Natl Acad Sci U S A, 105, 8256, 10.1073/pnas.0801340105 Shental-Bechor, 2009, Folding of glycoproteins: toward undestanding the biophysics of the glycosylation code, Curr Opin Struct Biol, 19, 524, 10.1016/j.sbi.2009.07.002 Shields, 2002, Lack of fucose on human IgG1 N-linked oligosaccharide improves binding to human Fcgamma RIII and antibody-dependent cellular toxicity, J Biol Chem, 277, 26733, 10.1074/jbc.M202069200 Shinkawa, 2003, The absence of fucose but not the presence of galactose or bisecting N-acetylglucosamine of human IgG1 complex-type oligosaccharides shows the critical role of enhancing antibody-dependent cellular cytotoxicity, J Biol Chem, 278, 3466, 10.1074/jbc.M210665200 Slámová, 2010, 4-Deoxysubstrates for β-N-acetylhexosaminidases: how to make use of their loose specificity, Glycobiology, 20, 1002, 10.1093/glycob/cwq058 Smoot, 2009, Oligosaccharide synthesis: from conventional methods to modern expeditious strategies, Adv Carbohydr Chem Biochem, 62, 161, 10.1016/S0065-2318(09)00005-5 Sommaruga, 2011, Highly efficient production of anti-HER2 scFv antibody variant for targeting breast cancer cells, Appl Microbiol Biotechnol, 91, 613, 10.1007/s00253-011-3306-3 Srivastava, 2008, Synthesis of the trisaccharide repeating unit related to Klebsiella 012 serotype, Carbohydr Res, 343, 2822, 10.1016/j.carres.2008.08.006 Stallforth, 2008, De novo synthesis of a d-galacturonic acid thioglycoside as key to the total synthesis of a glycosphingolipid from Sphingomonas yanoikuyae, Org Lett, 10, 1573, 10.1021/ol800227b Standfuss, 2011, The structural basis of agonist-induced activation in constitutively active rhodopsin, Nature, 471, 656, 10.1038/nature09795 Strasser, 2008, Generation of glyco-engineered Nicotiana benthamiana for the production of monoclonal antibodies with a homogeneous human-like N-glycan structure, Plant Biotechnol J, 6, 392, 10.1111/j.1467-7652.2008.00330.x Sun, 1995, Production and characterization of recombinant human proteinase inhibitor 6 expressed in Pichia pastoris, Biochem Biophys Acta, 1252, 28 Tanaka, 2005, Efficient stereoselective synthesis of gamma-N-glycosyl asparagines by N-glycosylation of primary amide groups, J Am Chem Soc, 127, 1630, 10.1021/ja0450298 Thibodeaux, 2008, Natural-product sugar biosynthesis and enzymatic glycodiversification, Angew Chem Int Ed, 47, 9814, 10.1002/anie.200801204 Truman, 2009, Chimeric glycosyltransferases for the generation of hybrid glycopeptides, Chem Biol, 16, 676, 10.1016/j.chembiol.2009.04.013 Verez-Bencomo, 2004, A synthetic conjugate saccharide vaccine against Haemophilus influenzae, Science, 305, 522, 10.1126/science.1095209 Vervecken, 2004, In vivo synthesis of mammalian-like, hybrid- type N-glycans in Pichia pastoris, Appl Environ Microbiol, 70, 2639, 10.1128/AEM.70.5.2639-2646.2004 Wacker, 2002, N-linked glycosylation in Campylobacter jejuni and its functional transfer into E. coli, Science, 298, 1790, 10.1126/science.298.5599.1790 Wagner, 2003, The (2-phenyl-2-trimethylsilyl)ethyl-(PTMSEL)-linker in the synthesis of glycopeptide partial structures of complex cell surface glycoproteins, Chemistry, 9, 6018, 10.1002/chem.200305304 Walsh, 2003, Biopharmaceutical benchmarks 2003, Nat Biotechnol, 21, 865, 10.1038/nbt0803-865 Walsh, 2010, Biopharmaceutical benchmarks 2010, Nat Biotechnol, 28, 917, 10.1038/nbt0910-917 Wang, 2001, Toward fully synthetic homogeneous glycoproteins: a high mannose core containing glycopeptide carrying full H-Type 2 human blood group specificity, Angew Chem Int Ed, 40, 1728, 10.1002/1521-3773(20010504)40:9<1728::AID-ANIE17280>3.0.CO;2-1 Wang, 2008, Chemoenzymatic syntheses of tumor-associated carbohydrate antigen Globo-H and stage-specific embryonic antigen 4, Adv Synth Catal, 350, 1717, 10.1002/adsc.200800129 Wang, 2011, Concise synthesis of Bacillus anthracis exosporium tetrasaccharide via two-stage activation of allyl glycosyl donor strategy, Tetrahedron Lett, 52, 3912, 10.1016/j.tetlet.2011.05.089 Weishaupt, 2010, Solid phase synthesis of oligosaccharides, Methods Enzymol, 478, 463, 10.1016/S0076-6879(10)78022-8 Williams, 2007, Expanding the promiscuity of a natural-product glycosyltransferase by directed evolution, Nat Chem Biol, 3, 657, 10.1038/nchembio.2007.28 Williams, 2008, Optimizing glycosyltransferase specificity via ‘hot spot’ saturation mutagenesis presents a catalyst for novobiocin glycorandomization, Chem Biol, 15, 393, 10.1016/j.chembiol.2008.02.017 Williams, 2011, Recombinant E. coli prototype strains for in vivo glycorandomization, ACS Chem Biol, 6, 95, 10.1021/cb100267k Wong, 1995, Advances in the use of Bacillus subtilis for the expression and secretion of heterologous proteins, Curr Opin Struct Biol, 5, 517 Wu, 2008, Synthesis and immunochemical characterization of S-linked glycoconjugate vaccines against Candida albicans, Chem Eur J, 14, 6474, 10.1002/chem.200800352 Wuhrer, 2007, Glycoproteomics based on tandem mass spectrometry of glycopeptides, J Chromatogr B Analyt Technol Biomed Life Sci, 15, 115, 10.1016/j.jchromb.2006.09.041 Xia, 2004, A draft sequence for genome of the domesticated silkworm (Bombyx mori), Science, 306, 1937, 10.1126/science.1102210 Yamane-Ohnuki, 2004, Establishment of FUT8 knockout Chinese hamster ovary cells: an ideal host cell line for producing completely defucosylated antibodies with enhanced antibody-dependent cellular cytotoxicity, Biotechnol Bioeng, 87, 614, 10.1002/bit.20151 Yan, 2005, Unraveling the mechanism of protein N-glycosylation, J Biol Chem, 280, 3121, 10.1074/jbc.R400036200 Yu, 2005, One-pot glycosylation for the chemical synthesis of oligosaccharides, Curr Org Chem, 9, 179, 10.2174/1385272053369240 Zanni, 2009, The Golgi α-1,6-mannosyltransferase KlOch1p of Kluyveromyces lactis is required for Ca2+/calmodulin-based signaling and for proper mitochondrial functionality, BMC Cell Biol, 10, 86, 10.1186/1471-2121-10-86 Zhang, 1999, Programmable one-pot oligosaccharide synthesis, J Am Chem Soc, 121, 734, 10.1021/ja982232s Zhou, 2008, Development of a simple and rapid method for producing non-fucosylated oligomannose containing antibodies with increased effector function, Biotechnol Bioeng, 99, 652, 10.1002/bit.21598 Zubarev, 1998, Electron capture dissociation of multiply charged protein cations. A nonergonic process, J Am Chem Soc, 120, 3265, 10.1021/ja973478k