Sucrose phosphorylases catalyze transglycosylation reactions on carboxylic acid compounds

Biologia

Volumn 63, Issue 6, 2008, Pages 1015-1019

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

^a EZAKI GLICO CO LTD   (Japan)

^b Osaka Prefecture University   (Japan)

Author keywords

Acetic acid; Benzoic acid; Carboxylic acid; Sucrose phosphorylase; Transglycosylation

Indexed keywords

LEUCONOSTOC MESENTEROIDES; STREPTOCOCCUS MUTANS;

EID: 57349169628     PISSN: 00063088     EISSN: 13369563     Source Type: Journal    
DOI: 10.2478/s11756-008-0161-5     Document Type: Review

References (20)

1. Clarke D.J. & Burchell B. 1994. The uridine diphosphate glucuronosyltransferase multigene family: function and regulation, pp. 3-43. In: Kauffman F.C. (ed.) Handbook of Experimental Pharmacology, Vol. 112, Conjugation-Deconjugation Reactions in Drug Metabolism and Toxicity, Springer-Verlag, Budapest.
2. M. Doudoroff 1943 Studies on the phosphorolysis of sucrose J. Biol. Chem. 151 351 361
3. Fenselau C. 1994. Acyl glucuronides as chemically reactive intermediates, pp. 367-389. In: Kauffman F.C. (ed.) Handbook of Experimental Pharmacology, Vol. 112, Conjugation-Deconjugation Reactions in Drug Metabolism and Toxicity, Springer-Verlag, Budapest.
4. K. Fujii M. Iiboshi M. Yanase T. Takaha T. Kuriki 2006 Enhancing the thermal stability of sucrose phosphorylase from Streptococcus mutans by random mutagenesis J. Appl. Glycosci. 53 91 97
5. M. Funayama H. Arakawa R. Yamamoto T. Nishino T. Shin S. Murao 1995 Effects of α-and β-arbutin on activity of tyrosinases from mushroom and mouse melanoma Biosci. Biotechnol. Biochem. 59 143 144
6. M. Kishi M. Fukaya Y. Tsukamoto T. Nagasawa K. Takehana N. Nishizawa 1999 Enhancing effect of dietary vinegar on the intestinal absorption of calcium in ovariectomized rats Biosci. Biotechnol. Biochem. 63 905 910
7. S. Kitao H. Sekine 1994 α-d-Glucosyl transfer to phenolic compounds by sucrose phosphorylase from Leuconostoc mesenteroides and production of α-arbutin Biosci. Biotechnol. Biochem. 58 38 42
8. K. Kitaoka H. Takahashi K. Hara H. Hashimoto T. Sasaki H. Taniguchi 1994 Purification and characterization of sucrose phosphorylase from Leuconostoc mesenteroides ATCC 12291 cells, and disaccharides synthesis by the enzyme Oyo Toshitsu Kagaku 41 165 172
9. T. Kometani Y. Terada T. Nishimura T. Hiroshi 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. S. Kondo K. Tayama Y. Tsukamoto K. Ikeda Y. Yamori 2001 Antihypertensive effects of acetic acid and vinegar on spontaneously hypertensive rats Biosci. Biotechnol. Biochem. 65 2690 2694
11. rd Ed., Academic Press, New York.
12. O. Mirza L.K. Skov D. Sprogøe L.A. van den Broek G. Beldman J.S. Kastrup M. Gajhede 2006 Structural rearrangements of sucrose phosphorylase from Bifidobacterium adolescentis during sucrose conversion J. Biol. Chem. 281 35576 35584
13. H. Nakano T. Kiso K. Okamoto T. Tomita M.B. Manan S. Kitahata 2003 Synthesis of glycosyl glycerol by cyclodextrin glucanotransferases J. Biosci. Bioeng. 95 583 588
14. T. Nishimura T. Kometani H. Takii Y. Terada S. Okada 1994 Purification and some properties of α-amylase from Bacillus subtilis X-23 that glucosylates phenolic compounds such as hydroquinone J. Ferment. Bioeng. 78 31 36
15. K. Nomura K. Sugimoto H. Nishiura K. Ohdan T. Nishimura H. Hayashi T. Kuriki 2008 Glucosylation of acetic acid by sucrose phosphorylase Biosci. Biotechnol. Biochem. 72 82 87
16. H. Spahn-Langguth L.Z. Benet 1992 Acyl glucuronides revisited: is the glucuronidation process a toxification as well as a detoxification mechanism? Drug Metab. Rev. 24 5 48
17. K. Sugimoto T. Nishimura K. Nomura K. Sugimoto T. Kuriki 2003 Syntheses of arbutin-α-glycosides and a comparison of their inhibitory effects with those of α-arbutin and arbutin on human tyrosinase Chem. Pharm. Bull. 51 798 801
18. K. Sugimoto K. Nomura T. Nishimura T. Kiso K. Sugimoto T. Kuriki 2005 Syntheses of α-arbutin-α-glycosides and their inhibitory effects on human tyrosinase J. Biosci. Bioeng. 99 272 276
19. K. Sugimoto K. Nomura H. Nishiura K. Ohdan T. Nishimura H. Hayashi T. Kuriki 2007 Novel transglucosylating reaction of sucrose phosphorylase to carboxylic compounds such as benzoic acid J. Biosci. Bioeng. 104 22 29
20. F. Takenaka H. Uchiyama 2000 Synthesis of α-d-glucosylglycerol by α-glucosidase and some of its characteristics Biosci. Biotechnol. Biochem. 64 1821 1826