Document Detail

The first total synthesis of (+/-)-4-methoxydecanoic acid: a novel antifungal fatty acid.
MedLine Citation:
PMID:  20161109     Owner:  NLM     Status:  Publisher    
The hitherto unknown (+/-)-4-methoxydecanoic acid was synthesized in six steps and in 25% overall yield starting from commercially available 4-penten-1-ol. The title compound demonstrated seventeen fold higher antifungal activity (MIC = 1.5 mM) against Candida albicans ATCC 60193 and Cryptococcus. neoformans ATCC 66031 when compared to unsubstituted n-decanoic acid. Our results demonstrate that Mid-chain methoxylation appears to be a viable strategy for increasing the fungitoxicity of fatty acids.
Néstor M Carballeira; Carlos Miranda; Keykavous Parang
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Publication Detail:
Journal Detail:
Title:  Tetrahedron letters     Volume:  50     ISSN:  0040-4039     ISO Abbreviation:  -     Publication Date:  2009 Oct 
Date Detail:
Created Date:  2010-7-13     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2984819R     Medline TA:  Tetrahedron Lett     Country:  -    
Other Details:
Languages:  ENG     Pagination:  5699-5700     Citation Subset:  -    
Department of Chemistry, University of Puerto Rico, Rio Piedras campus, PO BOX 23346, San Juan, Puerto Rico 00931.
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MeSH Terms
Grant Support
SC1 GM084708-01//NIGMS NIH HHS

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