Decoration of proteins with sugar chains: recent advances in glycoprotein synthesis

Dwek, 1996, Glycobiology: toward understanding the function of sugars, Chem Rev, 96, 683, 10.1021/cr940283b Walsh, 2006, Post-translational modifications in the context of therapeutic proteins, Nat Biotechnol, 24, 1241, 10.1038/nbt1252 Hojo, 2012, Chemoenzymatic synthesis of hydrophobic glycoprotein: synthesis of saposin C carrying complex-type carbohydrate, J Org Chem, 77, 9437, 10.1021/jo3010155 Huang, 2012, Chemoenzymatic glycoengineering of intact IgG antibodies for gain of functions, J Am Chem Soc, 134, 12308, 10.1021/ja3051266 Izumi, 2012, Chemical synthesis of intentionally misfolded homogeneous glycoprotein: a unique approach for the study of glycoprotein quality control, J Am Chem Soc, 134, 7238, 10.1021/ja3013177 Murakami, 2012, Chemical synthesis of an erythropoietin glycoform containing a complex-type disialyloligosaccharide, Angew Chem Int Ed, 51, 3567, 10.1002/anie.201109034 Sakamoto, 2012, Chemical synthesis of homogeneous human glycosyl-interferon-β that exhibits potent antitumor activity in vivo, J Am Chem Soc, 134, 5428, 10.1021/ja2109079 Wilkinson, 2012, Total synthesis of homogeneous antifreeze glycopeptides and glycoproteins, Angew Chem Int Ed, 51, 3606, 10.1002/anie.201108682 Asahina, 2013, Chemoenzymatic synthesis of the immunoglobulin domain of Tim-3 carrying a complex-type N-glycan by using a one-pot ligation, Angew Chem Int Ed, 52, 9733, 10.1002/anie.201303073 Orwenyo, 2013, Chemoenzymatic synthesis and lectin recognition of a selectively fluorinated glycoprotein, Bioorg Med Chem, 21, 4768, 10.1016/j.bmc.2013.03.009 Sato, 2013, Chemical synthesis of biologically active monoglycosylated GM2-activator protein analogue using N-sulfanylethylanilide peptide, Angew Chem Int Ed, 52, 7855, 10.1002/anie.201303390 Wang, 2013, Erythropoietin derived by chemical synthesis, Science, 342, 1357, 10.1126/science.1245095 Okamoto, 2014, Total chemical synthesis and biological activities of glycosylated and non-glycosylated forms of the chemokines CCL1 and Ser-CCL1, Angew Chem Int Ed, 53, 5188, 10.1002/anie.201310574 Okamoto, 2014, (Quasi-)racemic X-ray structures of glycosylated and non-glycosylated forms of the chemokine Ser-CCL1 prepared by total chemical synthesis, Angew Chem Int Ed, 53, 5194, 10.1002/anie.201400679 Smith, 2014, Chemoenzymatic Fc glycosylation via engineered aldehyde tags, Bioconjugate Chem, 25, 788, 10.1021/bc500061s Zhang, 2014, Synthesis of granulocyte-macrophage colony-stimulating factor as homogeneous glycoforms and early comparisons with yeast cell-derived material, Proc Natl Acad Sci U S A, 111, 2885, 10.1073/pnas.1400140111 Mochizuki, 2014, Chemical synthesis of human adiponectin(19–107) bearing post-translational glycosylation, Tetrahedron Lett, 55, 3073, 10.1016/j.tetlet.2014.03.127 Aussedat, 2012, Total synthesis of the α-subunit of human glycoprotein hormones: toward fully synthetic homogeneous human follicle-stimulating hormone, J Am Chem Soc, 134, 3532, 10.1021/ja2111459 Gamblin, 2008, Glycoprotein synthesis: an update, Chem Rev, 109, 131, 10.1021/cr078291i Unverzagt, 2013, Chemical assembly of N-glycoproteins: a refined toolbox to address a ubiquitous posttranslational modification, Chem Soc Rev, 42, 4408, 10.1039/c3cs35485g Wang, 2014, Chemical and chemoenzymatic synthesis of glycoproteins for deciphering functions, Chem Biol, 21, 51, 10.1016/j.chembiol.2014.01.001 Aimoto, 1999, Polypeptide synthesis by the thioester method, Biopolymers, 51, 247, 10.1002/(SICI)1097-0282(1999)51:4<247::AID-BIP2>3.0.CO;2-W Kent, 2009, Total chemical synthesis of proteins, Chem Soc Rev, 38, 338, 10.1039/B700141J Cohen-Anisfeld, 1993, A practical, convergent method for glycopeptide synthesis, J Am Chem Soc, 115, 10531, 10.1021/ja00076a010 Ullmann, 2012, Convergent solid-phase synthesis of N-glycopeptides facilitated by pseudoprolines at consensus-sequence Ser/Thr residues, Angew Chem Int Ed, 51, 11566, 10.1002/anie.201204272 Wang, 2012, An advance in the chemical synthesis of homogeneous N-linked glycopolypeptides by convergent aspartylation, Angew Chem Int Ed, 51, 11571, 10.1002/anie.201205038 Chen, 2010, Study of on-resin convergent synthesis of N-linked glycopeptides containing a large high mannose N-linked oligosaccharide, J Am Chem Soc, 132, 3211, 10.1021/ja9104073 Kochendoerfer, 2003, Design and chemical synthesis of a homogeneous polymer-modified erythropoiesis protein, Science, 299, 884, 10.1126/science.1079085 Kajihara, 2004, Prompt chemoenzymatic synthesis of diverse complex-type oligosaccharides and its application to the solid-phase synthesis of a glycopeptide with Asn-linked sialyl-undeca- and asialo-nonasaccharides, Chem Eur J, 10, 971, 10.1002/chem.200305115 Higuchi, 1992, Role of sugar chains in the expression of the biological activity of human erythropoietin, J Biol Chem, 267, 7703, 10.1016/S0021-9258(18)42572-0 Feeney, 1974, A biological antifreeze: a glycoprotein in the blood of polar fishes lowers the freezing temperature, Am Sci, 62, 712 Kajihara, 2006, Convenient synthesis of a sialylglycopeptide-thioester having an intact and homogeneous complex-type disialyl-oligosaccharide, Carbohydr Res, 341, 1333, 10.1016/j.carres.2006.04.037 Jefferis, 2009, Glycosylation as a strategy to improve antibody-based therapeutics, Nat Rev Drug Discov, 8, 226, 10.1038/nrd2804 Dalziel, 2014, Emerging principles for the therapeutic exploitation of glycosylation, Science, 343 Goodfellow, 2012, An endoglycosidase with alternative glycan specificity allows broadened glycoprotein remodelling, J Am Chem Soc, 134, 8030, 10.1021/ja301334b 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 Li, 2005, Highly efficient endoglycosidase-catalyzed synthesis of glycopeptides using oligosaccharide oxazolines as donor substrates, J Am Chem Soc, 127, 9692, 10.1021/ja051715a Rising, 2006, Endohexosaminidase M: exploring and exploiting enzyme substrate specificity, ChemBioChem, 7, 1177, 10.1002/cbic.200600183 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 Izumi, 2013, Misfolded glycoproteins as probes for analysis of folding sensor enzyme UDP-glucose: glycoprotein glucosyltransferase, Trends Glycosci Glycotechnol, 25, 1, 10.4052/tigg.25.1 Parodi, 2000, Protein glycosylation and its role in protein folding, Annu Rev Biochem, 69, 69, 10.1146/annurev.biochem.69.1.69 Helenius, 2004, Roles of N-linked glycans in the endoplasmic reticulum, Annu Rev Biochem, 73, 1019, 10.1146/annurev.biochem.73.011303.073752 Makimura, 2012, Efficient synthesis of glycopeptide-α-thioesters with a high-mannose type oligosaccharide by means of tert-Boc-solid phase peptide synthesis, Carbohydr Res, 364, 41, 10.1016/j.carres.2012.10.011 Dedola, 2014, Folding of synthetic homogeneous glycoproteins in the presence of a glycoprotein folding sensor enzyme, Angew Chem Int Ed, 53, 2883, 10.1002/anie.201309665 Pentelute, 2008, X-ray structure of snow flea antifreeze protein determined by racemic crystallization of synthetic protein enantiomers, J Am Chem Soc, 130, 9695, 10.1021/ja8013538 Yeates, 2012, Racemic protein crystallography, Annu Rev Biophys, 41, 41, 10.1146/annurev-biophys-050511-102333