Selective N-Arylation of p-Aminophenylalanine in Unprotected Peptides with Organometallic Palladium Reagents
The Pentelute Lab aims to invent new chemistry for the efficient and selective modification of proteins, to ‘hijack’ these biological machines for efficient drug delivery into cells and to create new machines to rapidly and efficiently manufacture peptides and proteins.
Pentelute Lab, Chemistry, MIT, Chemistry Department, Boston, Cambridge, Biology, Peptides, Peptide, Proteins, Science, Rapid, Brad Pentelute, Brad,
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Selective N-Arylation of p-Aminophenylalanine in Unprotected Peptides with Organometallic Palladium Reagents

Selective N-Arylation of p-Aminophenylalanine in Unprotected Peptides with Organometallic Palladium Reagents

First published: 20 May 2021 https://doi.org/10.1002/anie.202104780


Aaron J. Mallek,Prof. Bradley L. Pentelute,Prof. Stephen L. Buchwald

Abstract

Pre-formed oxidative addition complexes (OACs) are utilized to selectively arylate p-aminophenylalanine (pAF) in the presence of native functional groups, except cysteine. In phosphate buffer pH 7.5, OACs derived from electron-poor arenes provide full conversion in as little as 2 hours at micromolar concentration. A complimentary procedure using the weak base 1,5-diazabicyclo(4.3.0)non-5-ene (DBN) is also presented enabling arylation with electron-rich substrates with up to 97 % conversion.

Category
2021, Publications