Document Detail


Conformationally restricted analog and biotin-labeled probe based on beauveriolide III.
MedLine Citation:
PMID:  22079027     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
A conformationally restricted oxazoline analog 7 was designed on the basis of a SAR study of beauveriolide III (2) and its analogs reported previously. Conformational analysis by molecular mechanics calculation suggested that the three side chains of 7 mostly occupy the same spaces as those of 2. The analog 7 was synthesized by peptide coupling of the d-cyclohexylglycine-containing ester 11 and d-Ser-containing dipeptide 12, macrolactamization, and cyclodehydration of 6 for the construction of an oxazoline ring. The bicyclic 7 exhibited potential inhibitory activity for cholesteryl ester synthesis similar to that by 2. These results revealed biologically important 3D spaces of the three side chains in inhibitory activity for cholesteryl ester synthesis. In addition, we accomplished the synthesis of a biotin-labeled probe 8 by copper-catalyzed (3+2) cycloaddition of a biotin-containing alkyne 16 and azido-containing beauveriolide analog 15 prepared from 6.
Authors:
Takayuki Doi; Terushige Muraoka; Taichi Ohshiro; Daisuke Matsuda; Masahito Yoshida; Takashi Takahashi; Satoshi Omura; Hiroshi Tomoda
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2011-10-21
Journal Detail:
Title:  Bioorganic & medicinal chemistry letters     Volume:  -     ISSN:  1464-3405     ISO Abbreviation:  -     Publication Date:  2011 Oct 
Date Detail:
Created Date:  2011-11-14     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9107377     Medline TA:  Bioorg Med Chem Lett     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Copyright Information:
Copyright © 2011 Elsevier Ltd. All rights reserved.
Affiliation:
Tohoku University, Graduate School of Pharmaceutical Sciences, 6-3 Aza-aoba, Aramaki, Aoba-ku, Sendai 980-8578, Japan.
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