Synthesis and Stereochemical Determination of the Peptide Antibiotic Novo29.

ABSTRACT: This paper describes the synthesis and stereochemical determination of Novo29 (clovibactin), a new peptide antibiotic that is related to teixobactin and is active against Gram-positive bacteria. Novo29 is an eight-residue depsipeptide that contains the noncanonical amino acid hydroxyasparagine of hitherto undetermined stereochemistry in a macrolactone ring. The amino acid building blocks Fmoc-(2R,3R)-hydroxyasparagine-OH and Fmoc-(2R,3S)-hydroxyasparagine-OH were synthesized from (R,R)- and (S,S)-diethyl tartrate. Novo29 and epi-Novo29 were then prepared by solid-phase peptide synthesis using these building blocks. Correlation with an authentic sample of Novo29 through ¹H NMR spectroscopy, LC-MS, and in vitro

SUBMITTER: Krumberger M 

PROVIDER: S-EPMC9942206 | biostudies-literature | 2023 Feb

REPOSITORIES: biostudies-literature