| Monoacylation of 2-O-alpha-D-glucopyranosyl-L-ascorbic acid by protease in N,N-dimethylformamide with low water content. | |
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MedLine Citation:
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PMID: 20566192 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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. |
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Authors:
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Akihiro Tai; Tasuku Mori; Yuka Kimura; Hideyuki Ito |
Publication Detail:
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Type: Journal Article Date: 2010-05-04 |
Journal Detail:
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Title: Carbohydrate research Volume: 345 ISSN: 1873-426X ISO Abbreviation: Carbohydr. Res. Publication Date: 2010 Aug |
Date Detail:
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Created Date: 2010-07-19 Completed Date: 2010-12-13 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 0043535 Medline TA: Carbohydr Res Country: Netherlands |
Other Details:
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Languages: eng Pagination: 1658-62 Citation Subset: IM |
Copyright Information:
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Copyright 2010 Elsevier Ltd. All rights reserved. |
Affiliation:
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Faculty of Life and Environmental Sciences, Prefectural University of Hiroshima, Shobara, Hiroshima 727-0023, Japan. atai@pu-hiroshima.ac.jp |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Acylation Ascorbic Acid / analogs & derivatives*, chemistry, metabolism Biocatalysis Carbohydrate Sequence Formamides* Molecular Conformation Peptide Hydrolases / metabolism* Stereoisomerism Water / analysis* |
| Chemical | |
Reg. No./Substance:
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0/Formamides; 0/N,N-dimethylformamide; 129499-78-1/ascorbic acid 2-O-glucoside; 50-81-7/Ascorbic Acid; 7732-18-5/Water; EC 3.4.-/Peptide Hydrolases |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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