Novel transglucosylating reaction of sucrose phosphorylase to carboxylic compounds such as benzoic acid

Journal of Bioscience and Bioengineering

Volumn 104, Issue 1, 2007, Pages 22-29

  Sugimoto, Kazuhisa ^a   Nomura, Koji ^a   Nishiura, Hiromi ^a   Ohdan, Kohji ^a   Hayashi, Hideo ^b   Kuriki, Takashi ^a  

^a EZAKI GLICO CO LTD   (Japan)

^b Natural Products Chemistry   (Japan)

Author keywords

benzoic acid; carboxylic compounds; carboxylic group; intramolecular acyl migration; sucrose; sucrose phosphorylase; transglucosylation

Indexed keywords

BENZOIC ACID; CARBOXYLIC COMPOUNDS; CARBOXYLIC GROUPS; INTRAMOLECULAR ACYL MIGRATION; SUCROSE PHOSPHORYLASE; TRANSGLUCOSYLATION;

FATTY ACIDS; MUTAGENS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION KINETICS; SUGAR (SUCROSE);

ENZYMES;

1 O BENZOYL ALPHA DEXTRO GLUCOPYRANOSIDE; 2 O BENZOYL ALPHA DEXTRO GLUCOPYRANOSE; 2 O BENZOYL BETA DEXTRO GLUCOPYRANOSE; BENZOIC ACID; CARBOXYL GROUP; DICARBOXYLIC ACID; HYDROXYACID; PHOSPHORYLASE; SHORT CHAIN FATTY ACID; SUCROSE; SUCROSE PHOSPHORYLASE; UNCLASSIFIED DRUG;

ACIDITY; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENZYME ACTIVITY; GLYCOSYLATION; LEUCONOSTOC MESENTEROIDES; MOLECULAR DYNAMICS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; STREPTOCOCCUS MUTANS;

BACTERIAL PROTEINS; BENZOIC ACID; GLUCOSIDES; GLUCOSYLTRANSFERASES; GLYCOSYLATION; LEUCONOSTOC; STREPTOCOCCUS MUTANS; SUBSTRATE SPECIFICITY; SUCROSE;

LEUCONOSTOC MESENTEROIDES; STREPTOCOCCUS MUTANS;

EID: 34547679566     PISSN: 13891723     EISSN: None     Source Type: Journal    
DOI: 10.1263/jbb.104.22     Document Type: Article

References (28)

1. Scheppach W., Sommer H., Kirchner T., Paganelli G.M., Bartram P., Christl S., Richter F., Dusel G., and Kasper H. Effect of butyrate enemas on the colonic mucosa in distal ulcerative colitis. Gastroenterology 103 (1992) 51-56
2. Scheppach W., Bartram P., Richter A., Richter F., Liepold H., Dusel G., Hofstetter G., Ruthlein J., and Kasper H. Effect of short-chain fatty acids on the human mucosa in vitro. J. Parenter. Enteral Nutr. 16 (1992) 43-48
3. Kim S.J., and Won T.H. The effect of glycolic acid on cultured human skin fibroblasts: cell proliferative effect and increased collagen synthesis. J. Dermatol. 25 (1998) 85-89
4. Nishimura T., Kometani T., Takii H., Terada Y., and Okada S. Purification and some properties of α-amylase from Bacillus subtilis X-23 that glucosylates phenolic compounds such as hydroquinone. J. Ferment. Bioeng. 78 (1994) 31-36
5. Ohdan K., Kuriki T., Takata H., Kaneko H., and Okada S. Introduction of raw starch-binding domains into Bacillus subtilis α-amylase by fusion with the starch-binding domain of Bacillus cyclomaltodextrin glucanotransferase. Appl. Environ. Microbiol. 66 (2000) 3058-3064
6. Sugimoto K., Nomura K., Nishimura T., Kiso T., Sugimoto K., and Kuriki T. Syntheses of α-arbutin-α-glycosides and their inhibitory effects on human tyrosinase. J. Biosci. Bioeng. 99 (2005) 272-276
7. Sugimoto K., Nishimura T., Nomura K., Sugimoto K., and Kuriki T. Syntheses of arbutin-α-glycosides and comparison of their inhibitory effects with those of α-arbutin and arbutin on human tyrosinase. Chem. Pharm. Bull. 51 (2003) 798-801
8. Sugimoto K., Nishimura T., Nomura K., Sugimoto K., and Kuriki T. Inhibitory effects of α-arbutin on melanin synthesis in cultured human melanoma cells and a three-dimentional human skin model. Biol. Pharm. Bull. 27 (2004) 510-514
9. Takenaka F., and Uchiyama H. Synthesis of α-d-glucosylglycerol by α-glucosidase and some of its characteristics. Biosci. Biotech. Biochem. 64 (2000) 1821-1826
10. Nishimura T., Kometani T., Takii H., Terada Y., and Okada S. Acceptor specificity in the glucosylation reaction of Bacillus subtilis X-23 α-amylase towards various phenolic compounds and the structure of kojic acid glucoside. J. Ferment. Bioeng. 78 (1994) 37-41
11. Ohdan K., Kuriki T., Kaneko H., Shimada J., Takada T., Fujimoto Z., Mizuno H., and Okada S. Characteristics of two forms of α-amylases and structural implication. Appl. Environ. Microbiol. 65 (1999) 4652-4658
12. Kuriki T., Kaneko H., Yanase M., Takata H., Shimada J., Handa S., Takeda T., Umeyama H., and Okada S. Controlling substrate preference and transglycosylation activity of neopullulanase by manipulating steric constraint and hydrophobicity in active center. J. Biol. Chem. 271 (1996) 17321-17329
13. Takata H., Kuriki T., Okada S., Takesada Y., Iizuka M., Minamiura N., and Imanaka T. Action of neopullulanase. J. Biol. Chem. 267 (1992) 18447-18452
14. Nakano H., Kiso T., Okamoto K., Tomita T., Manan M.B., and Kitahata S. Synthesis of glycosyl glycerol by cyclodextrin glucanotransferases. J. Biosci. Bioeng. 95 (2003) 583-588
15. Kitao S., and Sekine H. α-d-Glucosyl transfer to phenolic compounds by sucrose phosphorylase from Leuconostoc mesenteroides and production of α-arbutin. Biosci. Biotech. Biochem. 58 (1994) 38-42
16. Fujii K., Iiboshi M., Yanase M., Takaha T., and Kuriki T. Enhancing the thermal stability of sucrose phosphorylase from Streptococcus mutans by random mutagenesis. J. Appl. Glycosci. 53 (2006) 91-97
17. Silverstein R., Voet J., Reed D., and Abeles R.H. Purification and mechanism of action of sucrose phosphorylase. J. Biol. Chem. 242 (1967) 1338-1346
18. Clarke D.J., and Burchell B. The uridine diphosphate glucronosyltransferase multigene family: function and regulation. In: Kauffman F.C. (Ed). Handbook of experimental pharmacology, vol. 112. Conjugation-deconjugation reactions in drug metabolism and toxicity (1994), Springer-Verlag, Budapest 3-43
19. Mieyal J.J., and Abeles R.H. Disaccharide phosphorylases. In: Boyer P.D. (Ed). The enzymes. 3rd ed. vol. 7 (1972), Academic Press, New York 515-532
20. Kitao S., Ariga T., Matsudo T., and Sekine H. The syntheses of catechin-glucosides by transglycosylation with Leuconostoc mesenteroides sucrose phosphorylase. Biosci. Biotech. Biochem. 57 (1993) 2010-2015
21. Mieyal J.J., Simon M., and Abeles R.H. Mechanism of action of sucrose phosphorylase. J. Biol. Chem. 247 (1972) 532-542
22. Kitaoka K., Takahashi H., Hara K., Hashimoto H., Sasaki T., and Taniguchi H. Purification and characterization of sucrose phosphorylase from Leuconostoc mesenteroides ATCC 12291 cells, and disaccharides synthesis by the enzyme. Oyo Toshitsu Kagaku 41 (1994) 165-172
23. Fenselau C. Acyl glucuronides as chemically reactive intermediates. In: Kauffman F.C. (Ed). Handbook of experimental pharmacology, vol. 112. Conjugation-deconjugation reactions in drug metabolism and toxicity (1994), Springer-Verlag, Berlin 367-389
24. Spahn-Langguth H., and Benet L.Z. Acyl glucuronides revisited: Is the glucuronidation process a toxification as well as a detoxification mechanism. Drug Metab. Rev. 24 (1992) 5-48
25. Fisher E. Migration of the acyl in glycerides. Chem. Ber. 53 (1920) 1621-1633
26. Adachi S., and Kobayashi T. Synthesis of esters by immobilized-lipase-catalyzed condensation reaction of sugars and fatty acids in water-miscible organic solvent. J. Biosci. Bioeng. 99 (2005) 87-94
27. Arcos J.A., Bernabe M., and Otero C. Quantitative enzymatic production of 6-O-acylglucose esters. Biotechnol. Bioeng. 57 (1998) 505-509
28. Ljunger G., Adlercreutz P., and Mattiasson B. Lipase catalyzed acylation of glucose. Biotechnol. Lett. 16 (1994) 1167-1172