Synthesis of a 2,4,6,8,10-dodecapentanoic acid thioester as a substrate for biosynthesis of Heat Stable Antifungal Factor (HSAF).
TheN-acetylcystamine (SNAC) thioester of dodecapentaenoic acid, an analog of a putative intermediate in the biosynthesis of Heat Stable Antifungal Factor (HSAF), is synthesized. Key steps include sequential Horner-Emmons homologations with the Weinreb amide of diethylphosponoacetic acid, and thioesterification of an aldol-derived 3-hydroxyalkanoate, which serves as a stable precursor of the sensitive polyenoate. The thioester was investigated as a biosynthetic substrate using a purified nonribosomal peptide synthetase and was not incorporated in the observed products.
Department of Chemistry, University of Nebraska-Lincoln Lincoln, NE 68588-0304.
Andrew S
AS
Olson
Department of Chemistry, University of Nebraska-Lincoln Lincoln, NE 68588-0304.
Haotong
H
Chen
Department of Chemistry, University of Nebraska-Lincoln Lincoln, NE 68588-0304.
Liangcheng
L
Du
Department of Chemistry, University of Nebraska-Lincoln Lincoln, NE 68588-0304.
Patrick H
PH
Dussault