A high-yielding biocatalytic process for the production of 2-O-(α-D-glucopyranosyl)-sn-glycerol, a natural osmolyte and useful moisturizing ingredient

Angewandte Chemie - International Edition

Volumn 47, Issue 52, 2008, Pages 10086-10089

  Goedl, Christiane ^a   Sawangwan, Thornthan ^a   Mueller, Mario ^a   Schwarz, Alexandra ^a   Nidetzky, Bernd ^a  

^a GRAZ UNIVERSITY OF TECHNOLOGY   (Austria)

Author keywords

Enzymatic synthesis; Glycosides; Kinetics; Regioselectivity; Transglucosylation

Indexed keywords

GLYCEROL; REGIOSELECTIVITY; SUGAR (SUCROSE); SUGARS;

BIOCATALYTIC PROCESSES; ENZYMATIC SYNTHESIS; GLYCOSIDES; GLYCOSYLTRANSFERASES; GLYCOSYNTHASES; HIGH YIELDS; OSMOLYTE; SUCROSE PHOSPHORYLASES; TRANSGLUCOSYLATION;

SYNTHESIS (CHEMICAL);

GLUCOSIDE; GLUCOSYLGLYCEROL; GLYCOSIDASE; MULTIENZYME COMPLEX; TRANSFERASE; TRANSGLYCOSIDASE ENZYME SYSTEM;

ARTICLE; BIOSYNTHESIS; CATALYSIS; CHEMISTRY;

CATALYSIS; GLUCOSIDES; GLYCOSIDE HYDROLASES; MULTIENZYME COMPLEXES; TRANSFERASES;

EID: 57749102704     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200803562     Document Type: Article

References (37)

1. a) H. Santos, P. Lamosa, T. Q. Faria, N. Borges, C. Neves in Physiology and Biochemistry of Extremophiles (Eds.: C. Gerday, N. Glansdorff), ASM Press, Washington, DC, 2007, pp. 86-103;
2. b) N. Empadinhas, M. S. da Costa, Int. Microbiol. 2006, 9, 199-206;
3. c) M. S. da Costa, H. Santos, E. A. Galinski, Adv. Biochem. Eng./Biotechnol. 1998, 61, 117-153.
4. a) G. Lentzen, T. Schwarz, Appl. Microbiol. Biotechnol. 2006, 72, 623-634;
5. b) "Orally used compatible solute containing agents": T. Schwarz, G. Lentzen, J. Krutmann, Germany, WO 2006097263, 2006.
6. D. K. Hincha, M. Hagemann, Biochem. J. 2004, 383, 277-283.
7. S. Fulda, J. Huckauf, A. Schoor, M. Hagemann, J. Plant Physiol. 1999, 154, 240-249.
8. a) "α-D-Glucopyranosyl glycerol derivatives as antiallergic agents, health foods, and cosmetics": K. Yoshida, A. Takenaka, T. Nitta, M. Iki, Japan, JP 2007137862, 2007;
9. b) "Cosmetic preparations containing glucosyl glycerides and one or more acrylamidomethyl propylsulphonic acid polymers": U. Breitenbach, V. Kallmayer, T. Raschke, C. Scherner, W. Siefken, S. Viala, Germany, WO 2006122669, 2006;
10. c) "Cosmetic preparations with an effective amount of glycosylglycerides as skin moisturizers": J. Thiem, O. Scheel, G. Schneider, Germany, EP 770378, 1997.
11. F. Takenaka, H. Uchiyama, Biosci. Biotechnol. Biochem. 2000, 64, 1821-1826.
12. a) "Antitumor agents containing α-D- glucopyranosylglycerols and food and cosmetics containing them": T. Nitta, A. Takenaka, M. Iki, E. Matsumura, M. Sakaguchi, JP 2007262023, 2007;
13. b) D. Colombo, F. Compostella, F. Ronchetti, A. Scala, L. Toma, H. Tokuda, H. Nishino, Eur. J. Med. Chem. 2000, 35, 1109-1113.
14. a) R. Suhr, O. Scheel, J. Thiem, J. Carbohydr. Chem. 1998, 17, 937-968;
15. b) N. Ohta, K. Achiwa, Chem. Pharm. Bull. 1991, 39, 1337-1339;
16. c) A. Roder, E. Hoffmann, M. Hagemann, G. Berg, FEMS Microbiol. Lett. 2005, 243, 219-226.
17. a) C. Goedl, A. Schwarz, M. Mueller, L. Brecker, B. Nidetzky, Carbohydr. Res. 2008, 343, 2032-2040;
18. b) J. J. Mieyal, R. H. Abeles, in The Enzymes, Vol. 7, 3rd ed., Academic Press, New York, 1972, pp. 515-532.
19. A. Schwarz, B. Nidetzky, FEBS Lett. 2006, 580, 3905-3910.
20. D. H. Crout, G. Vic, Curr. Opin. Chem. Biol. 1998, 2, 98-111.
21. M. Scigelova, S. Singh, D. H. G. Crout, J. Mol. Catal. B 1999, 6, 483-494.
22. H. Nakano, T. Kiso, K. Okamoto, T. Tomita, M. B. Manan, S. Kitahata, J. Biosci. Bioeng. 2003, 95, 583-588.
23. F. A. Shaikh, S. G. Withers, Biochem. Cell Biol. 2008, 86, 169-177.
24. a) M. Faijes, A. Planas, Carbohydr. Res. 2007, 342, 1581-1594;
25. b) G. Perugino, A. Trincone, M. Rossi, M. Moracci, Trends Biotechnol. 2004, 22, 31-37;
26. c) G. J. Davies, S. J. Charnock, B. Henrissat, Trends Glycosci. Glycotechnol. 2001, 13, 105-120.
27. S. Kitao, H. Sekine, Biosci. Biotechnol. Biochem. 1992, 56, 2011-2014.
28. O. Mirza, L. K. Skov, D. Sprogoe, L. A. van den Broek, G. Beldman, J. S. Kastrup, M. Gajhede, J. Biol. Chem. 2006, 281, 35576-35584.
29. a) E. J. Vandamme, J. van Loo, L. Machtelinckx, A. de Laporte, in Adv. Appl. Microbiol., Vol. 32, Academic Press, New York, 1987, pp. 163-201;
30. b) A. Schwarz, L. Brecker, B. Nidetzky, Biochem. J. 2007, 403, 441-449.
31. S. J. Williams, S. G. Withers, Carbohydr. Res. 2000, 327, 27-46.
32. S. M. Hancock, M. D. Vaughan, S. G. Withers, Curr. Opin. Chem. Biol. 2006, 10, 509-519.
33. "Preparation of 2-O-glyceryl-α-D- glucopyranoside from a glucosyl donor and a glucosyl acceptor": C. Goedl, T. Sawangwan, B. Nidetzky, M. Mueller, Austria, WO 2008034158, 2008.
34. C. Goedl, A. Schwarz, A. Minani, B. Nidetzky, J. Biotechnol. 2007, 129, 77-86.
35. M. Slatner, B. Nidetzky, K. D. Kulbe, Biochemistry 1999, 38, 10489-10498.
36. S. Saheki, A. Takeda, T. Shimazu, Anal. Biochem. 1985, 148, 277-281.
37. Y. W. Kim, H. Chen, S. G. Withers, Carbohydr. Res. 2005, 340, 2735-2741.