Total synthesis and further scrutiny of the in vitro antifungal activity of 6-nonadecynoic acid.
The antifungal, naturally occurring acetylenic fatty acid 6-nonadecynoic acid was synthesized in three steps (18 % overall yield), for the first time starting with commercially available 1-tetradecyne. The synthesis developed herein will facilitate the further study of the antifungal properties of this naturally occurring acetylenic fatty acid. The 6-nonadecynoic acid exhibited the best antifungal activity (< 4.3 microM) against Cryptococcus neoformans ATCC 66031 in Sabouraud Dextrose Broth (SDB) media. In our hands, it was not active against Candida albicans ATCC 14053 and Candida albicans ATCC 60193.
Carballeira
Néstor M
NM
Department of Chemistry, University of Puerto Rico, San Juan, Puerto Rico. ncarball@upracd.upr.clu.edu
Sanabria
David
D
Parang
Keykavous
K
D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001234:Aspergillus niger / Q000187:drug effects; D002176:Candida albicans / Q000187:drug effects; D003455:Cryptococcus neoformans / Q000187:drug effects; D005229:Fatty Acids, Monounsaturated / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D013329:Structure-Activity Relationship
C479851:6-nonadecynoic acid; D000935:Antifungal Agents; D005229:Fatty Acids, Monounsaturated