Synthesis of a 2,4,6,8,10-dodecapentanoic acid thioester as a substrate for biosynthesis of heat stable antifungal factor (HSAF)

Authors

Andrew S. Olson, University of Nebraska-LincolnFollow
Haotong Chen, University of Nebraska-Lincoln
Liangcheng Du, University of Nebraska-LincolnFollow
Patrick Dussault, University of Nebraska-LincolnFollow

Document Type

Article

Date of this Version

2015

Citation

RSC Adv., 2015, 5, 11644–11648

Comments

This journal is © The Royal Society of Chemistry 2015

Abstract

The N-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.