Synthesis of alkyl glycosides from cyclodextrin using cyclodextrin glycosyltransferase from Paenibacillus sp. RB01

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 70, Issue 3-4, 2011, Pages 359-368

  Chotipanang, Kwanjai ^a   Bhunthumnavin, Worawan ^a   Prousoontorn, Manchumas Hengsakul ^a  

^a CHULALONGKORN UNIVERSITY   (Thailand)

Author keywords

Alcohol; Alkyl glycoside; Cyclodextrin glycosyltransferase; Paenibacillus sp; Transglycosylation

Indexed keywords

EID: 80051789077     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-010-9888-z     Document Type: Conference Paper

References (35)

1. DB Sarney EN Vulfson 1995 Application of enzymes to the synthesis of surfactants Trends Biotechnol. 13 164 172 10.1016/S0167-7799(00)88933-7 1:CAS:528:DyaK2MXlvVans74%3D
2. F van Rantwijk M Woudenberg-van Oosterom RA Sheldon 1999 Glycosidase-catalysed synthesis of alkyl glycosides J. Mol. Catal. B. 6 511 532 10.1016/S1381-1177(99)00042-9 (Pubitemid 29232612)
3. K Lirdprapamongkol J Svasti 2000 Alkyl glucoside synthesis using Thai rosewood β- glucosidase Biotechnol. Lett. 22 1889 1894 10.1023/A: 1005696625268 1:CAS:528:DC%2BD3MXhtFWjsg%3D%3D (Pubitemid 32002226)
4. J Svasti T Phongsak R Sarnthima 2003 Transglucosylation of tertiary alcohols using cassava β-glucosidase Biochem. Biophys. Res. Commun. 305 470 475 10.1016/S0006-291X(03)00793-9 1:CAS:528:DC%2BD3sXjvFeku7w%3D (Pubitemid 36579253)
5. MR Martearena S Blanco G Ellenrieder 2003 Synthesis of alkyl-α-L-rhamnosides by water soluble alcohols enzymatic glycosylation Bioresour. Technol. 90 297 303 10.1016/S0960-8524(03)00131-7 1:CAS:528:DC%2BD3sXot1OhsL8%3D (Pubitemid 37324164)
6. K Makowski A Bialkowska J Olczak J Kur M Turkiewicz 2009 Antarctic, cold- adapted β-galactosidase of Pseudoalteromonas sp. 22b as an effective tool for alkyl galactopyranosides synthesis Enzym. Microb. Technol. 44 59 64 10.1016/j.enzmictec.2008.09.010 1:CAS:528:DC%2BD1cXhsFamur%2FN
7. AM Pereira FAA Costa MI Rodrigues F Maugeri 1998 In vitro synthesis of oligosaccharides by acceptor reaction of dextransucrase from Leuconostoc mesenteroides Biotechnol. Lett. 20 397 401 10.1023/A:1005387632760 1:CAS:528:DyaK1cXislCisb0%3D (Pubitemid 28181793)
8. CY Lee CY Yun JW Yun TK Oh CJ Kim 1997 Production of glucooligosaccharides by an acceptor reaction using two types of glucansucrase from Streptococcus sobrinus Biotechnol. Lett. 19 1227 1230 10.1023/A: 1018446122823 1:CAS:528:DyaK1cXltFWitg%3D%3D (Pubitemid 28010402)
9. PT Sangeetha MN Ramesh S.G Prapulla 2005 Fructooligosaccharide production using fructosyl transferase obtained from recycling culture of Aspergillus oryzae CFR 202 Process Biochem 40 1085 1088 10.1016/j.procbio.2004.03.009 1:CAS:528:DC%2BD2cXhtVaksbvN (Pubitemid 39568336)
10. MG Kim CH Kim JS Lee KB Song SK Rhee 2000 Synthesis of methyl β-D- fructoside catalyzed by levansucrase from Rahnella aquatilis Enzyme Microb. Technol. 27 646 651 10.1016/S0141-0229(00)00267-2
11. A Tonkova 1998 Bacterial cyclodextrin glucanotransferase. Enzyme Microb Technol 22 678 686 1:CAS:528:DyaK1cXjvFKktrc%3D (Pubitemid 28312623)
12. BA van der Veen JCM Uitdehaag BW Dijkstra L Dijkhuizen 2000 Engineering of cyclodextrin glycosyltransferase reaction and product specificity Biochim. Biophys. Acta 1543 336 360 10.1016/S0167-4838(00)00233-8 (Pubitemid 32057098)
13. S Kitahata K Hara K Fujita H Nakano N Kuwahara K Koizumi 1992 Acceptor specificity of cyclodextrin glycosyltransferase from Bacillus stearothermophilus and synthesis of α-D-glucosyl O-β-D-galactosyl-(1 → 4)-β-D-glucoside Biosci. Biotechnol. Biochem. 56 1386 1391 10.1271/bbb.56.1386 1:CAS:528:DyaK3sXhsVagsLg%3D
14. W Wongsangwattana J Kaulpiboon K Ito P Pongsawasdi 2010 Synthesis of cellobiose-containing oligosaccharides by intermolecular transglucosylation of cyclodextrin glycosyltransferase from Paenibacillus sp A11 Process Biochem. 45 947 953 10.1016/j.procbio.2010.02.024 1:CAS:528:DC%2BC3cXlt1Ciu7s%3D
15. T Kometani Y Terada T Nishimura H Takii S Okada 1994 Transglycosylation to hesperidin by cyclodextrin glucanotransferase from an alkalophilic Bacillus species in alkaline pH and properties of hesperidin glycosides Biosci. Biotechnol. Biochem. 58 1990 1994 10.1271/bbb.58.1990 1:CAS:528: DyaK2MXisVCrtLc%3D
16. H Zhao H Naito Y Ueda K Okada K Sadagane M Izumi S Nakajima N Baba 2008 Cyclomaltodextrin glucanotransferase-catalyzed transglycosylation from dextrin to alkanol maltosides Biosci. Biotechnol. Biochem 72 3006 3010 10.1271/bbb.80295 1:CAS:528:DC%2BD1cXhsVOjt7bJ
17. D Svensson S Ulvenlund P Adlercreutz 2009 Enzymatic route to alkyl glycosides having oligomeric head groups Green Chem. 11 1222 1226 10.1039/b904849a 1:CAS:528:DC%2BD1MXpsFSitbk%3D
18. D Svensson S Ulvenlund P Adlercreutz 2009 Efficient synthesis of a long carbohydrate chain alkyl glycoside catalyzed by cyclodextrin glycosyltransferase (CGTase) Biotechnol. Bioeng. 104 854 861 10.1002/bit.22472 1:CAS:528: DC%2BD1MXhtlSqs7jE
19. R Mosi S He J Uitdehaag BW Dijkstra SG Withers 1997 Trapping and characterization of the reaction intermediate in cyclodextrin glycosyltransferase by use of activated substrates and a mutant enzyme Biochemistry 36 9927 9934 10.1021/bi970618u 1:CAS:528:DyaK2sXlsVShur8%3D (Pubitemid 27364705)
20. H Aga M Yoneyama S Sakai I Yamamoto 1991 Synthesis of 2-O-α-D-glucopyranosyl L-ascorbic acid by cyclomaltodextrin glucanotransferase from Bacillus stearothermophilus Agric. Biol. Chem. 55 1751 1756 1:CAS:528:DyaK3MXlsFOjs7g%3D
21. M Tanaka N Muto I Yamamoto 1991 Characterization of Bacillus stearothermophilus cyclodextrin glucanotransferase in ascorbic acid 2-O-α-D-glucoside formation Biochim. Biophys. Acta 1078 127 132 10.1016/0167-4838(91)99000-1 1:CAS:528:DyaK3MXkvVyitrw%3D
22. HK Jun KM Bae SK Kim 2001 Production of 2-O-α-D-glucopyranosyl L-ascorbic acid using cyclodextrin glucanotransferase from Paenibacillus sp Biotechnol. Lett. 23 1793 1797 10.1023/A:1012413301061 1:CAS:528: DC%2BD3MXosl2rtLs%3D (Pubitemid 33072442)
23. MH Prousoontorn S Pantana 2007 Production of 2-O-α-glucopyranosyl L-ascorbic acid from ascorbic acid and β-cyclodextrin using immobilized cyclodextrin glycosyltransferase J. Incl. Phenom. Macrocycl. Chem. 57 39 46 10.1007/s10847-006-9163-5 1:CAS:528:DC%2BD2sXjs12mtb8%3D
24. M Funayama T Nishino A Hirota S Murao S Takenishi H Nakano 1993 Enzymatic synthesis of (+) catechin-α-glucoside and its effect on Tyrosinase activity Biosci. Biotechnol. Biochem 57 1666 1669 10.1271/bbb.57.1666 1:CAS:528:DyaK2cXhtVShs7Y%3D (Pubitemid 2009148)
25. D Penninga B Strokopytov HJ Rozeboom CL Lawson BW Dijkstra J Bergsma L Dijkhuizen 1995 Site-directed mutations in tyrosine 195 of cyclodextrin glycosyltransferase from Bacillus circulans strain 251 affect activity and product specificity Biochemistry 34 3368 3376 10.1021/bi00010a028 1:CAS:528:DyaK2MXjvFOktL0%3D
26. R Charoensakdi M Iizuka K Ito V Rimphanitchayakit T Limpaseni 2007 A recombinant cyclodextrin glycosyltransferase cloned from Paenibacillus sp. strain RB01 showed improved catalytic activity in coupling reaction between cyclodextrins and disaccharides J. Incl. Phenom. Macrocycl. Chem. 57 53 59 10.1007/s10847-006-9162-6 1:CAS:528:DC%2BD2sXjs12msrw%3D
27. K Horikoshi 1971 Production of alkaline enzymes by alkalophilic microorganisms Agric. Biol. Chem. 35 1783 1791 1:CAS:528:DyaE38Xht1ehurs%3D
28. T Kato K Horikoshi 1984 Immobilized cyclomaltodextrin glucanotransferase of an alkalophilic Bacillus sp. No. 38-2 Biotechnol. Bioeng. 26 595 598 10.1002/bit.260260606 1:CAS:528:DyaL2cXksFSrsrc%3D (Pubitemid 14077331)
29. J Kaulpiboon P Pongsawasdi 2005 Purification and characterization of cyclodextrinase from Paenibacillus sp A11 36 168 175 1:CAS:528:DC%2BD2MXjtlKh
30. MM Bradford 1976 A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding Anal. Biochem. 72 248 254 10.1016/0003-2697(76)90527-3 1:CAS:528: DyaE28XksVehtrY%3D
31. H Fuwa 1954 A new method for microdetermination of amylase activity by the use of amylose as the substrate J. Biochem. 41 583 603 1:CAS:528: DyaG2MXitVChtQ%3D%3D
32. T Kaneko T Kato N Nakamura K Horikoshi 1987 Spectrophotometric determination of cyclization activity of β-cyclodextrin forming cyclomaltodextrin glucanotransferase J. Jpn. Soc. Starch Sci. 34 45 48 1:CAS:528:DyaL2sXlvFemuro%3D
33. A Goel SN Nene 1995 Modifications in the phenolphthalein method for spectrophotometric estimation of beta cyclodextrin Starch/starke 47 399 400 10.1002/star.19950471006 1:CAS:528:DyaK2MXovVertrY%3D
34. J Larsson D Svensson P Adlercreutz 2005 α-Amylase-catalysed synthesis of alkyl glycosides J. Mol. Catal. B. 37 84 87 10.1016/j.molcatb.2005. 09.009 1:CAS:528:DC%2BD2MXht1GnurrJ (Pubitemid 41674653)
35. Z Chahid D Montet M Pina J Graille 1992 Effect of water activity on enzymatic synthesis of alkylglycosides Biotechnol. Lett. 14 281 284 10.1007/BF01022324 1:CAS:528:DyaK38XktVKjtr8%3D