| Lipase-catalyzed enantioselective esterification of mono-aza-benzo-15-crown-5-ether derivatives in organic media. | |
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MedLine Citation:
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PMID: 15604788 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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For the purpose of developing a new chiral crown ether unit as a chiral synthon, three racemic mono azabenzo-15-crown-5-ethers, i.e. (R,S)-1-(6,7,9,10,12,13,15,16-octahydro-5,8,14,17-tetraoxa-11-aza-benzocyclopentadecen-11-yl)-propan-2-ol, (R,S)-2-(6,7,9,10,12,13,15,16-octahydro-5,8,14,17-tetraoxa-11-aza-benzocyclopentadecen-11-yl)-1-phenyl-ethanol and (R , S)-1-[2-(6,7,9,10,12,13,15,16-octahydro-5,8,14,17-tetraoxa-11-aza-benzocyclopentadecen-11-ylmethyl)-phenyl]-ethanol were esterified with vinyl acetate using a lipase from Candida antarctica. The enzymatic acylation of alcohols produced monoacylated products. Two optically active azacrown ethers, (R)-propionic acid 1-methyl-2-(6,7,9,10,12,13,15,16-octahydro-5,8,14,17-tetraoxa-11-aza-benzocyclopentadecen-11-yl)-ethyl ester and (R)-acetic acid 1-[2-(6,7,9,10,12,13,15,16-octahydro-5,8,14,17-tetraoxa-11-aza-benzocyclopentadecen-11-ylmethyl)-phenyl]-ethyl ester were obtained within 48% and 36% yields, respectively and, at an enantiometric excess of over 99% in each case. |
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Authors:
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Tatsuro Kijima; Noriyasu Sato; Taeko Izumi |
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Publication Detail:
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Type: Comparative Study; Journal Article |
Journal Detail:
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Title: Biotechnology letters Volume: 26 ISSN: 0141-5492 ISO Abbreviation: Biotechnol. Lett. Publication Date: 2004 Oct |
Date Detail:
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Created Date: 2004-12-17 Completed Date: 2005-05-16 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 8008051 Medline TA: Biotechnol Lett Country: Netherlands |
Other Details:
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Languages: eng Pagination: 1505-9 Citation Subset: IM |
Affiliation:
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Department of Chemistry and Chemical Engineering, Faculty of Engineering, Yamagata University, 4-3-16 Jonan, Yonezawa, Yamagata 992-8510, Japan. kijima@yz.yamagata-u.ac.jp |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Catalysis Crown Ethers / chemistry* Esterification Isomerism Lipase / chemistry* Organic Chemicals / chemistry* Sensitivity and Specificity |
| Chemical | |
Reg. No./Substance:
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0/Crown Ethers; 0/Organic Chemicals; 33100-27-5/15-crown-5; EC 3.1.1.3/Lipase |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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