Issue 94, 2024

Loss of fluorine during crosslinking by the biarylitide P450Blt proceeds due to restricted peptide orientation

Abstract

The biarylitide crosslinking enzyme P450Blt can perform crosslinking between m-F-Tyr-3 and His-5 residues within peptide substrates with concomitant and specific loss of fluorine. Our investigations suggest that a small intrinsic preference for coupling ipso to fluorine is magnified by the binding of the peptide in a specific orientation that enforces the loss of fluorine during peptide crosslinking, likely via a two-step reaction mechanism involving the non-enzyme catalysed reductive elimination of fluoride.

Graphical abstract: Loss of fluorine during crosslinking by the biarylitide P450Blt proceeds due to restricted peptide orientation

Supplementary files

Article information

Article type
Communication
Submitted
11 Aug 2024
Accepted
04 Nov 2024
First published
05 Nov 2024

Chem. Commun., 2024,60, 13951-13954

Loss of fluorine during crosslinking by the biarylitide P450Blt proceeds due to restricted peptide orientation

Y. Zhao, J. Gullick, M. H. Hansen, L. Coe, M. Treisman, R. B. Schittenhelm, A. McKay, L. A. M. Murray, J. Tailhades, J. J. De Voss, E. H. Krenske and M. J. Cryle, Chem. Commun., 2024, 60, 13951 DOI: 10.1039/D4CC04092A

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