Efficient synthesis of a long carbohydrate chain alkyl glycoside catalyzed by cyclodextrin glycosyltransferase (CGTase)

Biotechnology and Bioengineering

Volumn 104, Issue 5, 2009, Pages 854-861

  Svensson, David ^a   Ulvenlund, Stefan ^b   Adlercreutz, Patrick ^a  

^a LUND UNIVERSITY   (Sweden)

^b ASTRAZENECA R AND D   (Sweden)

Author keywords

Alkyl glycoside; Coupling reaction; Cyclodextrin; Cyclodextrin glycosyltransferase; Dodecyl D maltooctaoside; Transglycosylation

Indexed keywords

ALKYL GLYCOSIDE; ALKYLGLYCOSIDES; BACILLUS MACERANS; CARBOHYDRATE CHAINS; COUPLING REACTION; CYCLODEXTRIN GLYCOSYLTRANSFERASE; DISPROPORTIONATION REACTIONS; EFFICIENT SYNTHESIS; GLYCOSYL DONORS; HIGH YIELD; KINETIC CONTROL; PRODUCT RANGES; SINGLE-STEP; TRANSGLYCOSYLATION;

ALKYLATION; BACTERIOLOGY; CATALYSIS; CATALYSTS; ENZYMES; ORGANIC COMPOUNDS; SULFUR COMPOUNDS; SURFACE ACTIVE AGENTS; SYNTHESIS (CHEMICAL);

SUGARS;

CARBOHYDRATE DERIVATIVE; CYCLOMALTODEXTRIN GLUCANOTRANSFERASE; DODECYL BETA DEXTRO MALTOOCTAOSIDE; DODECYL BETA DEXTRO MALTOSIDE; GLYCOSIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; NONHUMAN; PH MEASUREMENT; SYNTHESIS; TEMPERATURE MEASUREMENT; THERMOANAEROBACTER;

ALPHA-CYCLODEXTRINS; BACILLUS; GLUCOSIDES; GLUCOSYLTRANSFERASES; GLYCOSIDES; MODELS, CHEMICAL; SURFACE-ACTIVE AGENTS; THERMOANAEROBACTER;

PAENIBACILLUS MACERANS; THERMOANAEROBACTER;

EID: 70350534537     PISSN: 00063592     EISSN: 10970290     Source Type: Journal    
DOI: 10.1002/bit.22472     Document Type: Article

References (41)

1. Bender H. 1978. (1 → 4)-alpha-D-Glucopyranosyltransfer-produkte aus cyclohexaamylose. Carbohydr Res 65(1):85-97.
2. Bernat V, Ringard-Lefebvre C, Le Bas G, Perly B, Djedaieni-Pilard F, Lesieur S. 2008. Inclusion complex of n-octyl-beta-D-glucopyranoside and alpha-cyclodextrin in aqueous solutions: Thermodynamic and structural characterization. Langmuir 24(7):3140-3149. (Pubitemid 351549151)
3. Boyd BJ, Drummond CJ, Krodkiewska I, Grieser F. 2000. How chain length, headgroup polymerization, and anomeric configuration govern the thermotropic and lyotropic liquid crystalline phase behavior and the air-water interfacial adsorption of glucose-based surfactants. Langmuir 16(19):7359-7367. (Pubitemid 30939146)
4. Casu B, Grenni A, Naggi A, Torri G, Virtuani M, Focher B. 1990. Interaction of cyclodextrins (cyclomalto-oligosaccharides) with glycolipids: n.m.r. studies of aqueous systems of cyclo-maltohexaose and alkyl glycosides. Carbohydr Res 200:101-109.
5. Dols-Lafargue M, Willemot R-M, Monsan PF, Remaud-Simeon M. 2001. Factors affecting alpha,-1,2 glucooligosaccharide synthesis by Leuconostoc mesenteroides NRRL B-1299 dextransucrase. Biotechnol Bioeng 74(6):498-504. (Pubitemid 32821754)
6. Ericsson CA, Ericsson LC, Kocherbitov V, Soederman O, Ulvenlund S. 2005a. Thermotropic phase behaviour of long-chain alkylmaltosides. Phys Chem Chem Phys 7(15):2970-2977. (Pubitemid 41168557)
7. Ericsson CA, Soderman O, Garamus VM, Bergstrom M, Ulvenlund S. 2005b. Effects of temperature, salt, and deuterium oxide on the selfaggregation of alkylglycosides in dilute solution. 2. n-Tetradecyl-beta- D-maltoside. Langmuir 21(4):1507-1515.
8. Gomez de Segura A, Alcalde M, Bernabe M, Ballesteros A, Plou FJ. 2006. Synthesis of methyl alpha-D-glucooligosaccharides by entrapped dextransucrase from Leuconostoc mesenteroides B-1299. J Biotechnol 124(2):439-445. (Pubitemid 43912930)
9. Hamada H, Nishida K, Furuya T, Ishihara K, Nakajima N. 2001. Preparation of a new pepper: Chemoenzymatic synthesis of capsaicin oligosaccharide and 8-nordihydrocapsaicin oligosaccharide. J Mol Catal B Enzymatic 16(2):115-119. (Pubitemid 33016366)
10. Hiroyuki D, Toshiyuki S, Kohtaro K, Kuniki K, Shoji U. 2002. Enzymatic synthesis of l-menthyl alpha-maltoside and l-menthyl alpha-maltooligosides from l-menthyl alpha-glucoside by cyclodextrin glucanotransferase. J Biosci Bioeng 94(2):119-123.
11. Kim Y-M, Okuyama M, Mori H, Nakai H, Saburi W, Chiba S, Kimura A. 2005. Enzymatic synthesis of alkyl alpha-2-deoxyglucosides by alkyl alcohol resistant alpha-glucosidase from Aspergillus niger. Tetrahedron Asymmetry 16(2):403-409. (Pubitemid 40174820)
12. Kobayashi T, Adachi S, Nakanishi K, Matsuno R. 2000. Synthesis of alkyl glycosides through beta-glucosidase-catalyzed condensation in an aqueous-organic biphasic system and estimation of the equilibrium constants for their formation. J Mol Catal B Enzymatic 11:13-21.
13. Kochikyan VT, Markosyan AA, Abelyan LA, Balayan AM, Abelyan VA. 2006. Combined enzymatic modification of stevioside and rebaudioside A. Appl Biochem Microbiol 42(1):31-37.
14. Kometani T, Terada Y, Nishimura T, Takii H, Okada S. 1994. Purification and characterization of cyclodextrin glucanotransferase from an alkalophilic Bacillus species and transglycosylation at alkaline pHs. Biosci Biotechnol Biochem 58(3):517-520. (Pubitemid 2080951)
15. Kometani T, Terada Y, Nishimura T, Takii H, Okada S. 1995. Synthesis of hesperidin glycosides by cyclodextrin glucanotransferase and stabilization of the natural pigments. Nippon Shokuhin Kagaku Kogaku Kaishi 42(5):376-382.
16. Koshland DE, Jr. 1953. Stereochemistry and the mechanism of enzymic reactions. Biol Rev Camb Philos Soc 28:416-436.
17. Larsson J, Svensson D, Adlercreutz P. 2005. Alpha-Amylase-catalysed synthesis of alkyl glycosides. J Mol Catal B Enzymatic 37(1-6):84-87.
18. Ljunger G, Adlercreutz P, Mattiasson B. 1994. Enzymatic synthesis of octyl-beta- glucoside in octanol at controlled water activity. Enzyme Microb Technol 16:751-755. (Pubitemid 2134095)
19. Mine Y, Zhang L, Fukunaga K, Sugimura Y. 2005. Enhancement of enzyme activity and enantioselectivity by cyclopentyl methyl ether in the transesterification catalyzed by Pseudomonas cepacia lipase co-lyophilized with cyclodextrins. Biotechnol Lett 27(6):383-388. (Pubitemid 40572967)
20. Okada K, Zhao H, Izumi M, Nakajima S, Baba N. 2007. Glucosylation of sucrose laurate with cyclodextrin glucanotransferase. Biosci Biotechnol Biochem 71(3):826-829. (Pubitemid 46481454)
21. Park JY, Lee SO, Lee TH. 1999. Syntheses of 1-O-benzyl-alpha-glucoside and 1-O-benzyl-alpha-maltoside by transglycosylation of alpha-amylase from soluble starch in aqueous solution. Biotechnol Lett 21(1):81-86.
22. Pedersen S, Dijkhuizen L, Dijkstra BW, Jensen BF, Jorgensen ST. 1995. A better enzyme for cyclodextrins. Chemtech 25(12):19-25.
23. Popova EI, Topchieva IN. 2001. Complex formation between polyethylene oxide-containing nonionic surfactants and alpha- and beta-cyclodextrins. Russ Chem Bull 50(4):620-625. (Pubitemid 33328799)
24. Prousoontorn MH, Pantatan S. 2007. Production of 2-O-alpha-glucopyranosyl L-ascorbic acid from ascorbic acid and beta-cyclodextrin using immobilized cyclodextrin glycosyltransferase. J Incl Phenom Macro Chem 57(1-4):39-46.
25. Qi Q, Zimmermann W. 2005. Cyclodextrin glucanotransferase: From gene to applications. Appl Microbiol Biotechnol 66(5):475-485.
26. Richard G, Morel S, Willemot R-M, Monsan P, Remaud-Simeon M. 2003. Glucosylation of alpha-butyl- and alpha-octyl-D-glucopyranosides by dextransucrase and alternansucrase from Leuconostoc mesenteroides. Carbohydr Res 338(9):855-864. (Pubitemid 36398005)
27. Sarney DB, Vulfson EN. 1995. Application of enzymes to the synthesis of surfactants. Trends Biotechnol 13(5):164-172.
28. Sathishkumar M, Jeong ES, Yun SE, Mun SP, Rusling JF. 2008. Bicontinuous microemulsion as reaction medium for the beta-glucosidase-catalyzed synthesis of n-hexyl-beta-D-glucopyranoside. Enzyme Microb Technol 42(3):252-258.
29. Sato M, Nakamura K, Nagano H, Yagi Y, Koizumi K. 1992. Synthesis of glucosyl-inositol using a CGTase, isolation and characterization of the positional isomers, and assimilation profiles for intestinal bacteria. Biotechnol Lett 14(8):659-664.
30. Sjogren H, Ericsson CA, Evenas J, Ulvenlund S. 2005. Interactions between charged polypeptides and nonionic surfactants. Biophys J 89(6):4219-4233. (Pubitemid 41725641)
31. Srinivasulu S, Rao AGA. 1993. Kinetic and structural studies on the interaction of surfactants with lipoxygenase L1 from soybeans (Glycine max). J Agric Food Chem 41(3):366-371.
32. Suzuki Y, Suzuki K. 1991. Enzymic formation of 4G-alpha-D-glucopyranosyl- rutin. Agric Biol Chem 55(1):181-187.
33. Svensson D, Ulvenlund S, Adlercreutz P. 2009. Novel enzymatic route to alkyl glycosides having oligomeric head groups. Green Chem DOI: 10.1039/b904849a
34. Tramice A, Pagnotta E, Romano I, Gambacorta A, Trincone A. 2007. Transglycosylation reactions using glycosyl hydrolases from Thermotoga neapolitana, a marine hydrogen-producing bacterium. J Mol Catal B Enzymatic 47(1-2):21-27. (Pubitemid 46819150)
35. van Rantwijk F, Woudenberg-van Oosterom M, Sheldon RA. 1999. Glycosidase- catalyzed synthesis of alkyl glycosides. J Mol Catal B Enzymatic 6(6):511-532.
36. Vetter D, Thorn W, Brunner H, Konig WA. 1992. Directed enzymatic synthesis of linear and branched glucooligosaccharides, using cyclodextrin- glucanosyltransferase. Carbohydr Res 223:61-69.
37. von Rybinski W, Hill K. 1998. Alkyl polyglycosides-properties and applications of a new class of surfactants. Angew Chem Int Ed 37(10):1328-1345. (Pubitemid 28290232)
38. Wallenfels K, Foldi P, Niermann H, Bender H, Linder D. 1978. The enzymic synthesis, by transglucosylation of a homologous series of glycosidically substituted malto-oligosaccharides, and their use as amylase substrates. Carbohydr Res 60(2):359-368.
39. Yoon S-H, Robyt JF. 2006. Optimized synthesis of specific sizes of maltodextrin glycosides by the coupling reactions of Bacillus macerans cyclomaltodextrin glucanyltransferase. Carbohydr Res 341(2):210-218.
40. Zhao H, Naito H, Ueda Y, Okada K, Sadagane K, Izumi M, Nakajima S, Baba N. 2008. Cyclomaltodextrin glucanotransferase-catalyzed transglycosylation from dextrin to alkanol maltosides. Biosci Biotechnol Biochem 72(11):3006-3010.
41. Zheng M, Endo T, Zimmermann W. 2002. Synthesis of large-ring cyclodextrins by cyclodextrin glucanotransferases from bacterial isolates. J Inclusion Phenom 44(1-4):387-390. (Pubitemid 38075729)