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Titre du document / Document title

Sucrose phosphorylases catalyze transglycosylation reactions on carboxylic acid compounds

Auteur(s) / Author(s)

Sugimoto Kazuhisa (1) ; Nomura Koji (1) ; Nishiura Hiromi (1) ; Ohdan Kohji (1) ; Nishimura Takahisa (1) ; Hayashi Hideo (2) ; Kuriki Takashi (1) ;

Affiliation(s) du ou des auteurs / Author(s) Affiliation(s)

(1) Biochemical Research Laboratory, Ezaki Glico Co., Ltd., 555-8502, Osaka, Japan
(2) Graduate School of Life and Environmental Sciences, Osaka Prefecture University, 590-8531, Osaka, Japan

Résumé / Abstract

Two sucrose phosphorylases were employed for glycosylation of carboxylic acid compounds. Streptococcus mutans sucrose phosphorylase showed remarkable transglycosylating activity, especially under acidic conditions. Leuconostoc mesenteroides sucrose phosphorylase exhibited very weak transglycosylating activity. Three main products were detected from the reaction mixture using benzoic acid and sucrose as an acceptor and a donor molecule, respectively. These compounds were identified as 1-O-benzoyl α-d-glucopyranoside, 2-O-benzoyl α-d-glucopyranose, and 2-O-benzoyl β-d-glucopyranose by 1D-and 2D-NMR analyses of the isolated products and their acetylated products. Time-course analyses proved that 1-O-benzoyl α-d-glucopyranoside was initially produced by the transglycosylation reaction of the enzyme. 2-O-Benzoyl α-d-glucopyranose and 2-O-benzoyl β-d-glucopyranose were produced from 1-O-benzoyl α-d-glucopyranoside by intramolecular acyl migration reaction. S. mutans sucrose phosphorylase showed broad acceptor-specificity. This sucrose phosphorylase catalyzed transglycosylation to various carboxylic compounds such as short-chain fatty acids, hydroxy acids, dicarboxylic acids, and phenolic carboxylic acids. 1-O-Acetyl α-d-glucopyranoside was also enzymatically synthesized by transglucosylation reaction of the enzyme. The sensory test of acetic acid and the glucosides revealed that the sour taste of acetic acid glucosides was significantly lower than that of acetic acid.

Revue / Journal Title

Biologia    ISSN  1336-9563 

Source / Source

2008, vol. 63, no6, pp. 1015-1019 [5 page(s) (article)]

Langue / Language

Anglais

Editeur / Publisher

Springer, Heidelberg, ALLEMAGNE  (2004) (Revue)

Mots-clés d'auteur / Author Keywords

sucrose phosphorylase

;

transglycosylation

;

carboxylic acid

;

benzoic acid

;

acetic acid

;

Localisation / Location

35400060113058.0041

© Versita Warsaw and Springer-Verlag Berlin Heidelberg, 2008
Nº notice refdoc (ud4) : 20844960



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