Glycosynthases: A novel efficient synthetic tool for oligosaccharides

Progress in Biochemistry and Biophysics

Volumn 33, Issue 4, 2006, Pages 310-320

  Lu, Li Li ^a   Xiao, Min ^a   Zhao, Han ^a   Wang, Peng ^a   Qian, Xin Min ^a  

^a SHANDONG UNIVERSITY   (China)

Author keywords

Glycosidases; Glycosynthases; Improvement of characteristics; Oligosaccharides synthesis; Screening in high throughput assay

Indexed keywords

MAMMALIA;

EID: 33745995147     PISSN: 10003282     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (37)

1. Palcic M M. Biocatalytic synthesis of oligosaccharides. Curr Opin Biotechnol, 1999, 10 (6): 616-624
2. Zopf D, Roth S. Oligosaccharide anti-infective agents. Lancet, 1996, 347 (9007): 1017-1021
3. Crout D H, Vic G. Glycosidases and glycosyl transferases in glycoside and oligosaccharide synthesis. Curr Opin Chem Biol, 1998, 2(1): 98-111
4. Sears P, Wong C H. Toward automated synthesis of oligosaccharides and glycoproteins. Science, 2001, 291(5512): 2344-2350
5. Scigelova M, Singh S, Crout D H G. Glycosidases-a great synthetic tool. J Mol Catal B: Enzym, 1999, 6 (5): 483-494
6. Daines A M, Maltman B A, Flitsch S L. Synthesis and modifications of carbohydrates, using biotransformations. Curr Opin Chem Biol, 2004, 8(2):106-113
7. McCarter J D, Withers S G. Mechanisms of enzymatic glycoside hydrolysis. Curr Opin Struct Biol, 1994, 4 (6): 885-892
8. Rye C S, Withers S G. Glycosidase mechanisms. Curr Opin Chem Biol, 2000, 4 (5): 573-580
9. Mackenzie L F, Wang Q, Warren R A J, et al. Glycosynthases: mutant glycosidases for oligosaccharide synthesis. J Am Chem Soc, 1998, 120 (22): 5583-5584
10. Malet C, Planas A. From β-glucanase to β-glucansynthase: glycosyl transfer to α-glycosyl fluorides catalyzed by a mutant endoglucanase lacking its catalytic nucleophile. FEBS Lett, 1998, 440 (1-2): 208-212
11. Moracci M, Trincone A, Perugino G, et al. Restoration of the activity of active-site mutants of the hyperthermophilic β-glycosidase from Sulfolobus solfataricus: dependence of the mechanism on the action of external nucleophiles. Biochemistry, 1998, 37(49): 17262-17270
12. Trincone A, Perugino G, Rossi M, et al. A novel thermophilic glycosynthase that effects branching glycosylation. Bioorg Med Chem Lett, 2000, 10 (4): 365-368
13. Nashiru O, Zechel D L, Stall D, et al. β-Mannosynthase: synthesis of β-mannosides with a mutant β-mannosidase. Angew Chem Int Ed, 2001, 40 (2): 417-420
14. Jahn M, Stoll D, Warren R A J, et al. Expansion of the glycosynthase repertoire to produce defined manno-oligosaccharides. Chem Commun, 2003, (12): 1327-1329
15. Okuyama M, Mori H, Watanabe K, et al. α-Glucosidase mutant catalyzes "α-glycosynthase"-type reaction. Biosci Biotechnol Biochem, 2002, 66 (4): 928-933
16. Hrmova M, Imai T, Rutten S J, et al. Mutated barley (1,3) -β-D-glucan endohydrolases synthesize crystalline (1,3) -β-D-glucans. J Biol Chem, 2002, 277 (33): 30102-30111
17. Fairweather J K, Hrmova M, Rutten S J, et al. Synthesis of complex oligosaccharides by using a mutated (1,3)-β-D-glucan endohydrolase from barley. Chemistry, 2003, 9(11): 2603-2610
18. van Lieshout J, Faijes M, Nieto J, et al. Hydrolase and glycosynthase activity of endo-1,3-beta-glucanase from the thermophile Pyrococcus furiosus. Archaea, 2004, 1 (4): 285-292
19. Mayer C, Zechel D L, Reid S P, et al. The E358S mutant of Agrobacterium sp. β-glucosidase is a greatly improved glycosynthase. FEBS Lett, 2000, 466 (1): 40-44
20. Trincone A, Giordano A, Perugino G, et al. Glycosynthase-catalysed syntheses at pH below neutrality. Bioorg Med Chem Lett, 2003, 13 (22): 4039-4042
21. Jakeman D L, Withers S G. On expanding the repertoire of glycosynthases: mutant β-galactosidases forming β-(1,6)-linkages. Can J Chem, 2002, 80 (8): 866-870
22. Perugino G, Trincone A, Giordano A, et al. Activity of hyperthermophilic glycosynthases is significantly enhanced at acidic pH. Biochemistry, 2003, 42 (28): 8484-8493
23. Yang X P, Yang S J, Han B Z, et al. Chin J Biotech, 2005, 21(1): 84-91
24. Fairweather J K, Faijes M, Driguez H, et al. Specificity studies of Bacillus 1,3-1,4-β-glucanases and application to glycosynthase-catalyzed transglycosylation. Chem Biochem, 2002, 3(9): 866-873
25. Fort S, Boyer V, Greffe L, et al. Highly efficient synthesis of β-(1→ 4)-oligo- and -polysaccharides using a mutant cellulase. J Am Chem Soc, 2000, 122 (23): 5429-5437
26. Jahn M, Marles J, Warren R A J, et al. Thioglycoligases: mutant glycosidases for thioglycoside synthesis. Angew Chem Int Ed, 2003, 42 (3): 352-354
27. Jahn M, Chen H, Mullegger J, et al. Thioglycosynthases: double mutant glycosidases that serve as scaffolds for thioglycoside synthesis, Chem Commun, 2004, (3): 274-275
28. Perugino G, Trincone A, Rossi M, et al. Oligosaccharide synthesis by glycosynthases. Trends Biotechnol, 2004, 22 (1): 31-37
29. Jahn M, Withers S G. New approaches to enzymatic oligosaccharide synthesis: glycosynthases and thioglycoligases. Biocatal Biotransfor, 2003, 21 (4-5): 159-166
30. Tolborg J F, Petersen L, Jensen K J, et al. Solid-phase oligosaccharide and glycopeptide synthesis using glycosynthases. J Org Chem, 2002, 67 (12): 4143-4149
31. Williams S J, Withers S G. Glycosyl fluorides in enzymatic reactions. Carbohydr Res, 2000, 327 (1-2): 27-46
32. Withers S G. Mechanisms of glycosyl transferases and hydrolases. Carb Polymers, 2001, 44 (4): 325-337
33. Mayer C, Jakeman D L, Mah M, et al. Directed evolution of new glycosynthases from Agrobacterium β-glucosidase: a general screen to detect enzymes for oligosaccharide synthesis. Chem Biol, 2001, 8 (5): 437-443
34. Kim Y W, Lee S S, Warren R A J, et al. Directed evolution of a glycosynthase from Agrobacterium sp. increases its catalytic activity dramatically and expands its substrate repertoire. J Biol Chem, 2004, 279 (41): 42787-42793
35. Lin H, Tao H, Cornish V W. Directed evolution of a glycosynthase via chemical complementation. J Am Chem Soc, 2004, 126 (46): 15051-15059
36. Mullegger J, Jahn M, Chen H M, et al. Engineering of a thioglycoligase: randomized mutagenesis of the acid-base residue leads to the identification of improved catalysts. Protein Eng Des Sel, 2005, 18 (1): 33-40
37. Stick R V, Stubbs K A, Watts A G. Modifying the regioselectivity of glycosynthase reactions through changes in the acceptor. Aust J Chem, 2004, 57 (8): 779-786