Document Detail


Lipase-catalyzed enantioselective esterification of mono-aza-benzo-15-crown-5-ether derivatives in organic media.
MedLine Citation:
PMID:  15604788     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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.
Authors:
Tatsuro Kijima; Noriyasu Sato; Taeko Izumi
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Publication Detail:
Type:  Comparative Study; Journal Article    
Journal Detail:
Title:  Biotechnology letters     Volume:  26     ISSN:  0141-5492     ISO Abbreviation:  Biotechnol. Lett.     Publication Date:  2004 Oct 
Date Detail:
Created Date:  2004-12-17     Completed Date:  2005-05-16     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  8008051     Medline TA:  Biotechnol Lett     Country:  Netherlands    
Other Details:
Languages:  eng     Pagination:  1505-9     Citation Subset:  IM    
Affiliation:
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
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MeSH Terms
Descriptor/Qualifier:
Catalysis
Crown Ethers / chemistry*
Esterification
Isomerism
Lipase / chemistry*
Organic Chemicals / chemistry*
Sensitivity and Specificity
Chemical
Reg. No./Substance:
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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