Work

Total synthesis of micrococcin P1 and thiocillin I enabled by Mo( vi ) catalyst

Year: 2018

Type: article

Abstract: Thiopeptides are a class of potent antibiotics with promising therapeutic potential. We developed a novel Mo(vi)-oxide/picolinic acid catalyst for the cyclodehydration of cysteine peptides to form thiazoline heterocycles. With this powerful tool in hand, we completed the total syntheses of two representative thiopeptide antibiotics: micrococcin P1 and thiocillin I. These two concise syntheses (15 steps, longest linear sequence) feature a C-H activation strategy to install the trisubstituted pyridine core and thiazole groups. The synthetic material displays promising antimicrobial properties measured against a series of Gram-positive bacteria.

Source: Chemical Science

DOI: 10.1039/c8sc04885a

Authors: Siddhartha Akasapu, Aaron B. Hinds, Wyatt C. Powell, Maciej A. Walczak

Institution: University of Colorado Boulder

Language: English

Topic: Chemical Synthesis and Analysis

Subfield: Molecular Biology

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

Open Access status: diamond