Issue 5, 2017
From the journal:

Chemical Communications

Chemoselective and site-selective peptide and native protein modification enabled by aldehyde auto-oxidation†

Landa Purushottam,a   Srinivasa Rao Adusumalli,a   Maheshwerreddy Chilamaria  and  Vishal Rai ORCID logo *a  

* Corresponding authors

a Organic and Bioconjugate Chemistry Laboratory, Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhauri, Bhopal Bypass Road, Bhopal 462066, India
E-mail: vrai@iiserb.ac.in

Abstract

We report a chemoselective and site-selective formylation of ε-amine in native proteins. The aldehyde auto-oxidation re-routing, regulated generation of formate, and reversible N-terminus protection drive the transformation. It labels a single ε-amine in a pool of its copies, other nucleophilic residues, and α-amine. The extension of the methodology leads to site-selective acylation.

Graphical abstract: Chemoselective and site-selective peptide and native protein modification enabled by aldehyde auto-oxidation

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Article information

DOI
https://doi.org/10.1039/C6CC09555K
Article type
Communication
Submitted
01 Dec 2016
Accepted
19 Dec 2016
First published
19 Dec 2016

Chem. Commun., 2017,53, 959-962

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Chemoselective and site-selective peptide and native protein modification enabled by aldehyde auto-oxidation

L. Purushottam, S. R. Adusumalli, M. Chilamari and V. Rai, Chem. Commun., 2017, 53, 959 DOI: 10.1039/C6CC09555K

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