Monoacylation of 2-O-α-D-glucopyranosyl-L-ascorbic acid by protease in N,N-dimethylformamide with low water content

被引：6
|
作者：
Tai, Akihiro [1 ]
Mori, Tasuku [1 ]
Kimura, Yuka [2 ]
Ito, Hideyuki [2 ]
机构：
[1] Prefectural Univ Hiroshima, Fac Life & Environm Sci, Hiroshima 7270023, Japan
[2] Okayama Univ, Div Pharmaceut Sci, Grad Sch Med Dent & Pharmaceut Sci, Okayama 7008530, Japan
来源：
CARBOHYDRATE RESEARCH | 2010年 / 345卷 / 12期
关键词：
Protease; Transacylation; 2-O-alpha-D-Glucopyranosyl-L-ascorbic acid; Vinyl laurate; N; N-Dimethylformamide; Water; L-ASCORBIC-ACID; CATALYZED REGIOSELECTIVE ESTERIFICATION; BRANCHED-ACYL CHAIN; 6-O-ACYL-2-O-ALPHA-D-GLUCOPYRANOSYL-L-ASCORBIC ACIDS; COLLAGEN-SYNTHESIS; ALPHA-GLUCOSIDE; LIPASE; SUCROSE; TRANSGLUCOSYLATION; 2-GLUCOSIDE;
D O I：
10.1016/j.carres.2010.04.028
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
2-O-alpha-D-Glucopyranosyl-L-ascorbic acid (AA-2G) laurate was synthesized from AA-2G and vinyl laurate with a protease from Bacillus subtilis in N,N-dimethylformamide (DMF) with low water content. Addition of water to DMF dramatically enhanced monoacyl AA-2G synthesis. Maximum synthetic activity was observed when 3% (v/v) water was added to the reaction medium. Under the optimal reaction conditions, 5-O-dodecanoyl-2-O-alpha-D-glucopyranosyl-L-ascorbic acid, 2-O-(6'-O-dodecanoyl-alpha-D-glucopyranosyl)-L-ascorbic acid, and 6-O-dodecanoyl-2-O-alpha-D-glucopyranosyl-L-ascorbic acid were synthesized in yields of 5.5%, 3.2%, and 20.4%, respectively. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1658 / 1662
页数：5
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