Modulating OxyB-Catalyzed Cross-Coupling Reactions in Vancomycin Biosynthesis by Incorporation of Diverse d -Tyr Analogues

Seyma Ozturk, Clarissa C. Forneris, Andy K.L. Nguy, Erik J. Sorensen, Mohammad R. Seyedsayamdost

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

We report a general method for synthesizing diverse d-Tyr analogues, one of the constituents of the antibiotic vancomycin, using a Negishi cross-coupling protocol. Several analogues were incorporated into the vancomycin substrate-peptide and reacted with the biosynthetic enzymes OxyB and OxyA, which install the characteristic aromatic cross-links. We find that even small structural perturbations are not accepted by OxyA. The same modifications, however, enhance the catalytic capabilities of OxyB leading to the formation of a new macrocycle within the vancomycin framework.

Original languageEnglish (US)
Pages (from-to)7309-7317
Number of pages9
JournalJournal of Organic Chemistry
Volume83
Issue number13
DOIs
StatePublished - Jul 6 2018

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Modulating OxyB-Catalyzed Cross-Coupling Reactions in Vancomycin Biosynthesis by Incorporation of Diverse d -Tyr Analogues'. Together they form a unique fingerprint.

Cite this