β-Glycosidases: An alternative enzyme based method for synthesis of alkyl-glycosides

Yakimchuk OD, Kotomin AA, Petel’skii MB, Naumov VN: Cleaning action and surfactant properties of alkyl glucosides. Russ J Appl Chem. 2004, 77: 2001-2005. 10.1007/s11167-005-0208-0. Lin JT, Riedel S, Kinne R: The use of octyl-β-D-glucoside as detergent for hog kidney brush border membrane. Biochim Biophys Acta. 1979, 557: 179-187. 10.1016/0005-2736(79)90100-7. Svensson D, Ulvenlund S, Adlercreutz P: Enzymatic route to alkyl glycosides having oligomeric head groups. Green Chem. 2009, 11: 1222-1226. 10.1039/b904849a. Izawa S, Sakai-Tomito Y, Kinomura K, Kitazawa S, Tsuda M, Tsuchiya T: Introduction of a series of alkyl thiomaltosides, useful new non-ionic detergents, to membrane biochemistry. J Biochem. 1993, 113: 573-576. Drouet P, Zhang M, Legoy MD: Enzymatic synthesis of alkyl β-D-xylosides by transxylosylation and reverse hydrolysis. Biotechnol Bioeng. 1994, 43: 1075-1080. 10.1002/bit.260431110. Milkerert G, Garamus VM, Veermans K, Willumert R, Vill V: Strutures of micelles formed by dynthetic alkyl glycosides with unsaturated alkyl chains. J Coll Int Sci. 2005, 284: 704-713. 10.1016/j.jcis.2004.10.039. VanAken T, Foxall-vanAken S, Castleman S, Ferguson-Miller S: Alkyl glycoside detergents: synthesis and applications to the study of membrane proteins. Methods Enzymol. 1986, 125: 27-35. Von Rybinski W, Hill K: ChemInform Abstract: Alkyl polyglycosides — properties and applications of a new class of surfactants. Angew Chem Int Ed. 1998, 37: 1328-1345. 10.1002/(SICI)1521-3773(19980605)37:10<1328::AID-ANIE1328>3.0.CO;2-9. Tesmann H, Kahre J, Hensen H, Salka BA: Alkyl polyglycosides in personal care products. Alkyl Polyglycosides. Wiley-VCH Verlag GmbH. 2008, ch5: 71-98. Corma A, Iborra S, Miquel S, Primo J: Preparation of long-chain alkyl-glucoside surfactants by one-step direct Fischer glucosidation, and by transacetylation of butyl glucosides, on beta zeolite catalysts. J Catal. 1998, 180: 218-224. 10.1006/jcat.1998.2272. Igarashi K: The Koenigs-Knorr reaction. Adv Carbohydr Chem Biochem. 1977, 34: 243-283. Bojarová P, Křen V: Glycosidases: a key to tailored carbohydrates. Trends Biotechnol. 2009, 27: 199-209. 10.1016/j.tibtech.2008.12.003. Van Rantwijk F, Woudenberg-van Oosterom M, Sheldon RA: Glycosidase-catalysed synthesis of alkyl glycosides. J Mol Catal B: Enzym. 1999, 6: 511-632. 10.1016/S1381-1177(99)00042-9. Crout DHG, Vic G: Glycosidases and glycosyl transferases in glycoside and oligosaccharide synthesis. Curr Opin Chem Biol. 1998, 2: 98-111. 10.1016/S1367-5931(98)80041-0. Vulfson EN, Patel R, Law BA: Alkyl-β-glucoside synthesis in a water-organic two-phase system. Biotechnol Lett. 1990, 12: 397-402. 10.1007/BF01024392. Hansson T, Adlercreutz P: Enhanced transglucosylation/hydrolysis ratio of mutants of Pyrococcus furiosus β-glucosidase: Effects of donor concentration, water content, and temperature on activity and selectivity in hexanol. Biotechnol Bioeng. 2001, 75: 656-665. 10.1002/bit.10043. Basso A, Ducret A, Gardossi L, Lortie R: Synthesis of octyl glucopyranoside by almond β-glucosidase adsorbed onto Celite R-640®. Tetrahedron Lett. 2002, 43: 2005-2008. 10.1016/S0040-4039(02)00197-1. Gargouri M, Smaali I, Maugard T, Legoy MD, Marzouki N: Fungus β-glycosidases: immobilization and use in alkyl-β-glycoside synthesis. J Mol Catal B: Enzym. 2004, 29: 89-94. 10.1016/j.molcatb.2003.11.020. Kouptsova OS, Klyachko NL, Levashov AV: Synthesis of alkyl glycosides catalyzed by β-glycosidases in a system of reverse micelles. Russ J Bioorg Chem. 2001, 27: 380-384. 10.1023/A:1012936702457. Rather MY, Mishra S, Chand S: β-Glucosidase catalyzed synthesis of octyl-β-D-glucopyranoside using whole cells of Pichia etchellsii in micro aqueous media. J Biotechnol. 2010, 150: 490-496. Ismail A, Soultani S, Ghoul M: Enzymatic-catalyzed synthesis of alkyl-glycosides in monophasic and biphasic systems I. The transglycosylation reaction. J Biotechnol. 1999, 69: 135-143. 10.1016/S0168-1656(99)00041-3. Lang M, Kamrat T, Nidetzky B: Influence of ionic liquid cosolvent on transgalactosylation reactions catalyzed by thermostable β-glycosylhydrolase CelB from Pyrococcus furiosus. Biotechnol Bioeng. 2006, 95: 1093-1100. 10.1002/bit.21068. De Carvalho CCCR: Enzymatic and whole cell catalysis: finding new strategies for old processes. Biotechnol Adv. 2011, 29: 75-83. 10.1016/j.biotechadv.2010.09.001. Rather MY, Mishra S, Verma V, Chand S: Biotransformation of methyl-β-D-glucopyranoside to higher chain alkyl glucosides by cell bound β-glucosidase of Pichia etchellsii. Bioresour Technol. 2012, 107: 287-294. Rather MY, Mishra S, Aravinda S: Exploring the synthetic potential of cell bound β-glycosidase of Pichia etchellsii. J Biotechnol. 2013, 165: 63-68. 10.1016/j.jbiotec.2013.02.011. Das-Bradoo S, Svensson I, Santos J, Plieva F, Mattiasson B, Hatti-Kaul R: Synthesis of alkylgalactosides using whole cells of Bacillus pseudofirmus species as catalysts. J Biotechnol. 2004, 110: 273-286. 10.1016/j.jbiotec.2004.03.004. Ito J, Ebe T, Shibasaki S, Fukuda H, Kondo A: Production of alkyl glucoside from cellooligosaccharides using yeast strains displaying Aspergillus aculeatus β-glucosidase 1. J Mol Catal B: Enzym. 2007, 49: 92-97. 10.1016/j.molcatb.2007.08.008. Bae J, Choi EH, Pan JG: Efficient synthesis of octyl-β-D-galactopyranoside by Bacillus spore-displayed β-galactosidase using an amphiphilic 1,2-dimethoxyethane co-solvent. Enzyme Microb Technol. 2011, 48: 232-238. 10.1016/j.enzmictec.2010.11.002. Kwon SJ, Jung HC, Pan JG: Transgalactosylation in a water-solvent biphasic reaction system with β-galactosidase displayed on the surfaces of Bacillus subtilis spores. Appl Environ Microbiol. 2007, 73: 2251-2256. 10.1128/AEM.01489-06. Ly HD, Withers SG: Mutagenesis of glycosidases. Annu Rev Biochem. 1999, 68: 487-522. 10.1146/annurev.biochem.68.1.487. Mackenzie LF, Wang Q, Warren RAJ, Withers SG: Glycosynthases: mutant glycosidases for oligosaccharide synthesis. J Am Chem Soc. 1998, 120: 5583-5584. 10.1021/ja980833d. Villandier N, Corma A: Transformation of cellulose into biodegradable alkyl glycosides by following two different chemical routes. ChemSusChem. 2011, 4: 508-513. 10.1002/cssc.201000371. Roy B, Mukhopadhyay B: Sulfuric acid immobilized on silica: an excellent catalyst for Fischer type glycosylation. Tetrahedron Lett. 2007, 48: 3783-3787. 10.1016/j.tetlet.2007.03.165. Bornaghi LF, Poulsen SA: Microwave-accelerated Fischer glycosylation. Tetrahedron Lett. 2005, 46: 3485-3488. 10.1016/j.tetlet.2005.03.126. Wimmer Z, Pechova L, Saman D: Koenigs-Knorr synthesis of cycloalkyl glycosides. Molecules. 2004, 9: 902-912. 10.3390/91100902. Richel A, Laurent P, Wathelet B, Wathelet JP, Paquot M: Microwave-assisted conversion of carbohydrates. State of the art and outlook. Comptes Rendus Chimie. 2011, 14: 224-234. 10.1016/j.crci.2010.04.004. Panintrarux C, Adachi S, Araki Y, Kimura Y, Matsuno R: Equilibrium yield of n-alkyl-β-D-glucoside through condensation of glucose and -alcohol by β-glucosidase in a biphasic system. Enzyme Microb Technol. 2005, 17: 32-40. Chahid Z, Montet D, Pina M, Bonnot F, Graille J: Biocatalyzed octylglycoside synthesis from a disaccharide. Biotechnol Lett. 1994, 16: 795-800. 10.1007/BF00133956. Rye CS, Withers SG: Glycosidase mechanisms. Curr Opin Chem Biol. 2000, 4: 573-580. 10.1016/S1367-5931(00)00135-6. Withers SG: Mechanisms of glycosyltransferases and hydrolases. Carbohydr Polym. 2001, 44: 325-337. 10.1016/S0144-8617(00)00249-6. Davies G, Henrissat B: Structures and mechanisms of glycosyl hydrolases. Structure. 1995, 3: 853-859. 10.1016/S0969-2126(01)00220-9. McCarter JD, Stephen Withers G: Mechanisms of enzymatic glycoside hydrolysis. Curr Opin Struct Biol. 1994, 4: 885-892. 10.1016/0959-440X(94)90271-2. Desmet T, Soetaert W, Bojarová P, Křen V, Dijkhuizen L, Eastwick-Field V, Schiller A: Enzymatic glycosylation of small molecules: challenging substrates require tailored catalysts. Chem Euro J. 2012, 18: 10786-10801. 10.1002/chem.201103069. Cantarel BL, Coutinho PM, Rancurel C, Bernard T, Lombard V, Henrissat B: The Carbohydrate-Active EnZymes database (CAZy): an expert resource for Glycogenomics. Nucleic Acids Res. 2009, 37: D233-D238. 10.1093/nar/gkn663. Ketudat CJ, Esen A: β-Glucosidases. Cell Mol Life Sci. 2010, 67: 3389-3405. 10.1007/s00018-010-0399-2. Weignerova L, Bojarova P, Kren V: Glycosidases in synthesis. Carbohyd Chem Chem Biol Appro. 2009, 35: 310-332. De Roode BM, Franssen MCR, Padt A, Boom RM: Perspectives for the industrial enzymatic production of glycosides. Biotechnol Prog. 2003, 19: 1391-1402. 10.1021/bp030038q. Vic G, Hastings JJ, Crout DHG: Glycosidase-catalysed synthesis of glycosides by an improved procedure for reverse hydrolysis: application to the chemoenzymatic synthesis of galactopyranosyl-(1–4)-O-α-galactopyranoside derivatives. Tetrahed Asymm. 1996, 7: 1973-1984. 10.1016/0957-4166(96)00238-8. Stevenson DE, Stanley RA, Furneaux RH: Optimization of alkyl β-D-galactopyranoside synthesis from lactose using commercially available β-galactosidases. Biotechnol Bioeng. 1993, 42: 657-666. 10.1002/bit.260420514. Concie J, Levy GA, Whistler RL, Wolfrom ML, BeMiller JN: Methods in Carbohydrate Chemistry,Vol. II. 1963, New York: Academic Press, 335- Gibson RR, Dickinson RP, Boons GJ: Vinyl glycosides in oligosaccharide synthesis. 4. Glycosidase-catalyzed preparation of substituted allyl-glycosides. J Chem Soc Perkin Trans. 1997, 1: 3357-3360. Boons GJ, Isles S: Vinyl glycosides in oligosaccharide synthesis. 2. The use of allyl and vinyl glycosides in oligosaccharide synthesis. J Org Chem. 1996, 61: 4262-4271. 10.1021/jo960131b. Millqvist-Fureby A, Gill IS, Vulfson EN: Enzymatic transformations in supersaturated substrate solutions: I. A general study with glycosidases. Biotechnol Bioeng. 1998, 60: 190-196. 10.1002/(SICI)1097-0290(19981020)60:2<190::AID-BIT6>3.0.CO;2-I. Wang Q, Yu H, Zhao N, Li C, Shang Y, Liu H, Xu J: Significantly improved equilibrium yield of long-chain alkyl glucosides via reverse hydrolysis in a water-poor system using cross-linked almond meal as a cheap and robust biocatalyst. Chinese J Catal. 2012, 33: 275-280. 10.1016/S1872-2067(11)60333-1. Vic G, Thomas D, Crout DHG: Solvent effect on enzyme-catalyzed synthesis of β-D-glucosides using the reverse hydrolysis method: Application to the preparative-scale synthesis of 2-hydroxybenzyl and octyl β-D-glucopyranosides. Enzyme Microb Technol. 1997, 20: 597-603. 10.1016/S0141-0229(96)00201-3. Yan TR, Liau JC: Synthesis of alkyl β-glucosides from cellobiose with Aspergillus niger β-glucosidase II. Biotechnol Lett. 1998, 20: 653-657. 10.1023/A:1005362305545. Makropoulou M, Christakopoulos P, Tsitsimpikou C, Kekos D, Kolisis FN, Macris BJ: Factors affecting the specificity of β-glucosidase from Fusarium oxysporum in enzymatic synthesis of alkyl-β-D-glucosides. Int J Biol Macromol. 1998, 22: 97-101. 10.1016/S0141-8130(97)00092-5. Yan TR, Lin YH, Lin CL: Purification and characterization of an extracellular β-glucosidase II with high hydrolysis and transglucosylation activities from Aspergillus niger. J Agr Food Chem. 1998, 46: 431-437. 10.1021/jf9702499. Benešová E, Lipovová P, Dvořáková H, Králová B: β-D-Galactosidase from Paenibacillus thiaminolyticus catalyzing transfucosylation reactions. Glycobiol. 2010, 20: 442-451. 10.1093/glycob/cwp196. Gueguen Y, Chemardin P, Pommares P, Arnaud A, Galzy P: Enzymatic synthesis of dodecyl β-D-glucopyranoside catalyzed by Candida molischiana 35M5N β-glucosidase. Bioresour Technol. 1995, 53: 263-267. García-Garibay M, López-Munguía A, Barzana E: Alcoholysis and reverse hydrolysis reactions in organic one-phase system with a hyperthermophilic β-glycosidase. Biotechnol Bioeng. 2000, 69: 627-632. 10.1002/1097-0290(20000920)69:6<627::AID-BIT6>3.0.CO;2-7. Lirdprapamongkol K, Svasti J: Alkyl glucoside synthesis using Thai rosewood β-glucosidase. Biotechnol Lett. 2000, 22: 1889-1894. 10.1023/A:1005696625268. Ducret A, Trani M, Lortie R: Screening of various glycosidases for the synthesis of octyl glucoside. Biotechnol Bioeng. 2002, 77: 752-757. 10.1002/bit.10156. Papanikolaou S: Enzyme-catalyzed synthesis of alkyl-β-glucosides in a water-alcohol two-phase system. Bioresour Technol. 2001, 77: 157-161. 10.1016/S0960-8524(00)00153-X. Yi Q, Sarney DB, Khan JA, Vulfson EN: A novel approach to biotransformations in aqueous-organic two-phase systems: Enzymatic synthesis of alkyl β-D-glucosides using microencapsulated β-glucosidase. Biotechnol Bioeng. 1998, 60: 385-390. 10.1002/(SICI)1097-0290(19981105)60:3<385::AID-BIT16>3.0.CO;2-L. Turner P, Svensson D, Adlercreutz P, Karlsson EN: A novel variant of Thermotoga neapolitana β-glucosidase B is an efficient catalyst for the synthesis of alkyl glucosides by transglycosylation. J Biotechnol. 2007, 130: 67-74. 10.1016/j.jbiotec.2007.02.016. Smaali I, Maugard T, Limam F, Legoy M-D, Marzouki N: Efficient synthesis of gluco-oligosaccharides and alkyl-glucosides by transglycosylation activity of β-glucosidase from Sclerotinia sclerotiorum. World J Microb Biotechnol. 2007, 23: 145-149. 10.1007/s11274-006-9185-6. Makowski K, Białkowska A, Olczak J, Kur J, Turkiewicz M: Antarctic, cold-adapted β-galactosidase of Pseudoalteromonas sp. 22b as an effective tool for alkyl galactopyranosides synthesis. Enzyme Microb Technol. 2009, 44: 59-64. 10.1016/j.enzmictec.2008.09.010. Bilanikova D, Mastihuba V, Mastihubova M, Balesova J, Schmidt S: Improvements in enzymatic preparations of alkyl glycosides. Czech J Food Sci. 2010, 28: 69-73. Ochs M, Muzard M, Plantier-Royon R, Estrine B, Remond C: Enzymatic synthesis of alkyl β-D-xylosides and oligoxylosides from xylans and from hydrothermally pretreated wheat bran. Green Chem. 2011, 13: 2380-2388. 10.1039/c1gc15719a. Ljunger G, Adlercreutz P, Mattiasson B: Enzymatic synthesis of octyl-β-D-glucoside in octanol at controlled water activity. Enzyme Microb Technol. 1994, 16: 751-755. 10.1016/0141-0229(94)90031-0. Andersson M, Adlercreutz P: A kinetic study of almond β-glucosidase catalysed synthesis of hexyl-glycosides in low aqueous media. Influence of glycosyl donor and water activity. J Mol Catal B: Enzym. 2000, 607: 1-8. Bojarová P, Petrásková L, Ferrandi EE, Monti D, Pelantová H, Kuzma M: Glycosyl azides – an alternative way to disaccharides. Adv Synth Catal. 2007, 2007 (349): 1514-1520. Svasti J, Phongsak T, Sarnthima R: Transglucosylation of tertiary alcohols using cassava β-glucosidase. Biochem Biophys Res Commun. 2003, 305: 470-475. 10.1016/S0006-291X(03)00793-9. Zaks A, Klibanov AM: Enzymatic catalysis in nonaqueous solvents. J Biol Chem. 1998, 263: 3194-3201. Wallecha A, Mishra S: Purification and characterization of two β-glucosidases from a thermo-tolerant yeast Pichia etchellsii. Biochim Biophys Acta-Protein Struct Mech. 2003, 1649: 74-84. 10.1016/S1570-9639(03)00163-8. Zou ZZ, Yu HL, Li CX, Zhou XW, Hayashi C, Sun J: A new thermostable β-glucosidase mined from Dictyoglomus thermophilum: Properties and performance in octyl glucoside synthesis at high temperatures. Bioresour Technol. 2012, 118: 425-430. Basso A, De Martin L, Ebert C, Gardossi L, Linda P: High isolated yields in thermodynamically controlled peptide synthesis in toluene catalysed by thermolysin adsorbed on Celite R-640. Chem Commun. 2000, 6: 467-468. Park DW, Kim HS, Jung JK, Haam S, Kim WS: Enzymatic synthesis of alkyl-glucosides by amphiphilic phase enzyme reaction. Biotechnol Lett. 2000, 22: 951-956. 10.1023/A:1005620707624. Klyachko NL, Levashov AV: Bioorganic synthesis in reverse micelles and related systems. Curr Opin Colloid In. 2003, 8: 179-186. 10.1016/S1359-0294(03)00016-5. Earle MJ, Esperanca JMSS, Gilea MA, Canongia Lopes JN, Rebelo LPN, Magee JW: The distillation and volatility of ionic liquids. Nature. 2006, 439: 831-834. 10.1038/nature04451. Van Rantwijk F, Sheldon RA: Biocatalysis in ionic liquids. Chem Rev. 2007, 107: 2757-2785. 10.1021/cr050946x. Kragl U, Eckstein M, Kaftzik N: Enzyme catalysis in ionic liquids. Curr Opin Biotechnol. 2002, 13: 565-571. 10.1016/S0958-1669(02)00353-1. Earle M, Wasserscheid P, Schulz P, Olivier-Bourbigou H, Favre F, Vaultier M, Kirschning A, Singh V, Riisager A, Fehrmann R, Kuhlmann S: Organic synthesis. Edited by: Wasserscheid P, Wetton T. 2008, Weinheim: Wiley-VCH, 265-568. Gorke J, Srienc F, Kazlauskas R: Toward advanced ionic liquids. Polar, enzyme-friendly solvents for biocatalysis. Biotechnol Bioprocess Eng. 2010, 15: 40-53. 10.1007/s12257-009-3079-z. Kaftzik N, Wasserscheid P, Kragl U: Use of ionic liquids to increase the yield and enzyme stability in the β-galactosidase catalysed synthesis of N-acetyllactosamine. Org Process Res Dev. 2002, 6: 553-557. 10.1021/op0255231. Yang RL, Li N, Zong MH: Using ionic liquid co-solvents to improve enzymatic synthesis of arylalkyl β-D-glucopyranosides. J Mol Catal B: Enzym. 2012, 74: 24-28. 10.1016/j.molcatb.2011.08.009. Villandier N, Corma A: One pot catalytic conversion of cellulose into biodegradable surfactants. Chem Comm. 2010, 46: 4408-4410. 10.1039/c0cc00031k. Bornscheuer UT, Huisman GW, Kazlauskas RJ, Lutz S, Moore JC, Robins K: Engineering the third wave of biocatalysis. Nature. 2012, 485: 185-194. 10.1038/nature11117. Hancock SM, Corbett K, Fordham-Skelton AP, Gatehouse JA, Davis BG: Developing promiscuous glycosidases for glycoside synthesis: residues W433 and E432 in Sulfolobus solfataricus β-glycosidase are important glucoside- and galactoside-specificity determinants. ChemBioChem. 2005, 6: 866-875. 10.1002/cbic.200400341.