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

页码：1658 / 1662

页数：5

共 46 条

[1] Regioselective monoacylation of 2-O-α-D-glucopyranosyl-L-ascorbic acid by a polymer catalyst in N,N-dimethylformamide
Tai, Akihiro
Iwaoka, Yuji
Ito, Hideyuki
CARBOHYDRATE RESEARCH, 2011, 346 (15) : 2511 - 2514
[2] Protease-Catalyzed Monoacylation of 2-O-α-D-Glucopyranosyl-L-ascorbic Acid in Three Solvent Systems
Tai, Akihiro
Iwaoka, Yuji
Mori, Tasuku
Ito, Hideyuki
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2010, 74 (09) : 1969 - 1971
[3] Protease-catalyzed monoacylation of 2-O-α-D-glucopyranosyl-L-ascorbic acid in pyridine
Tai, A
Okazaki, S
Tsubosaka, N
Yamamoto, I
CHEMICAL & PHARMACEUTICAL BULLETIN, 2001, 49 (08) : 1047 - 1049
[4] Enhancing effect of 2-O-α-D-glucopyranosyl-L-ascorbic acid, a stable ascorbic acid derivative, on collagen synthesis
Kumano, Y
Sakamoto, T
Egawa, M
Tanaka, M
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[5] Producing 2-O-α-D-glucopyranosyl-L-ascorbic acid by modified cyclodextrin glucosyltransferase and isoamylase
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[6] Structural evidence for the DPPH radical-scavenging mechanism of 2-O-α-D-glucopyranosyl-L-ascorbic acid
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[7] Current studies on the enzymatic preparation 2-O-α-D-glucopyranosyl-L-ascorbic acid with cyclodextrin glycosyltransferase
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[8] Protection of free radical-induced cytotoxicity by 2-O-α-D-glucopyranosyl-L-ascorbic acid in human dermal fibroblasts
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