Work

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

Year: 2015

Type: article

Abstract: -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.

Source: RSC Advances

DOI: 10.1039/c4ra14829k

Authors: Andrew S. Olson, Haotong Chen, Liangcheng Du, Patrick H. Dussault

Institution: University of Nebraska–Lincoln

Language: English

Topic: Microbial Natural Products and Biosynthesis

Subfield: Pharmacology

Field: Medicine

Domain: Health Sciences

Open Access status: green

Funders: National Institutes of Health, National Institute of Allergy and Infectious Diseases, National Center for Research Resources

Awards: EXTRAMURAL RES FACILITIES CONSTR, Discovering New Anti-Infective Agents from Lysobacter