Synthesis of Cycloprodigiosin Identifies the Natural Isolate as a Scalemic Mixture.

ABSTRACT: The enantiomers of the natural product cycloprodigiosin were prepared using an expedient five-step synthetic sequence that takes advantage of a Schöllkopf-Barton-Zard (SBZ) pyrrole annulation with a chiral isocyanoacetate and a nitrocyclohexene derivative. Using chiral HPLC and X-ray crystallographic analyses of the synthetically prepared material and natural isolate (isolated from the marine bacterium Pseudoalteromonas rubra), naturally occurring cycloprodigiosin was determined to be a scalemic mixture occurring in an enantiomeric ratio of 83:17 (R)/(S) at C4'.

SUBMITTER: Johnson RE 

PROVIDER: S-EPMC4509414 | biostudies-literature | 2015 Jul

REPOSITORIES: biostudies-literature