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J Org Chem. 2018 Jul 6;83(13):7309-7317. doi: 10.1021/acs.joc.8b00916. Epub 2018 Jun 19.

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

Author information

1
Department of Chemistry , Princeton University , Princeton , New Jersey 08544 , United States.
2
Department of Molecular Biology , Princeton University , Princeton , New Jersey 08544 , United States.

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.

PMID:
29806454
DOI:
10.1021/acs.joc.8b00916
[Indexed for MEDLINE]

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