Enzymatic synthesis of salicin glycosides through transglycosylation catalyzed by amylosucrases from Deinococcus geothermalis and Neisseria polysaccharea.
Amylosucrase (ASase, EC 2.4.1.4) is a member of family 13 of the glycoside hydrolases that catalyze the synthesis of an alpha-(1-->4)-linked glucan polymer from sucrose instead of an expensive activated sugar, such as ADP- or UDP-glucose. Transglycosylation reactions mediated by the ASases of Deinococcus geothermalis (DGAS) and Neisseria polysaccharea (NPAS) were applied to the synthesis of salicin glycosides with sucrose serving as the glucopyranosyl donor and salicin as the acceptor molecule. Two salicin glycoside transfer products were detected by TLC and HPLC analyses. The synthesis of salicin glycosides was very efficient with NPAS with a yield of over 90%. In contrast, DGAS specifically synthesized only one salicin transglycosylation product. The transglycosylation products were identified as alpha-d-glucopyranosyl-(1-->4)-salicin (glucosyl salicin) and alpha-D-glucopyranosyl-(1-->4)-alpha-D-glucopyranosyl-(1-->4)-salicin (maltosyl salicin) by NMR analysis. The ratio between donor and acceptor had a significant effect on the type of product that resulted from the transglycosylation reaction. With more acceptors present in the reaction, more glucosyl salicin and less maltosyl salicin were synthesized.
Jung
Jong-Hyun
JH
Graduate School of Biotechnology, and Institute of Life Science and Resources, Kyung Hee University, Yongin 446-701, Republic of Korea.
Seo
Dong-Ho
DH
Ha
Suk-Jin
SJ
Song
Myoung-Chong
MC
Cha
Jaeho
J
Yoo
Sang-Ho
SH
Kim
Tae-Jip
TJ
Baek
Nam-In
NI
Baik
Moo-Yeol
MY
Park
Cheon-Seok
CS
D001592:Benzyl Alcohols / Q000737:chemistry*; D055162:Biocatalysis; D002240:Carbohydrate Sequence; D002851:Chromatography, High Pressure Liquid; D034301:Deinococcus / Q000201:enzymology*; D005947:Glucose / Q000737:chemistry / Q000378:metabolism; D005960:Glucosides; D005964:Glucosyltransferases / Q000096:biosynthesis / Q000302:isolation & purification / Q000378:metabolism*; D006027:Glycosides / Q000032:analysis / Q000737:chemistry / Q000378:metabolism*; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D009343:Neisseria / Q000201:enzymology*; D011994:Recombinant Proteins / Q000096:biosynthesis / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism; D013395:Sucrose / Q000737:chemistry / Q000378:metabolism; D013696:Temperature
D001592:Benzyl Alcohols; D005960:Glucosides; D006027:Glycosides; D011994:Recombinant Proteins; C005696:salicin; D013395:Sucrose; D005964:Glucosyltransferases; C019700:amylosucrase; D005947:Glucose