Cysteine-Selective Modification of Peptides and Proteins via Desulfurative C-C Bond Formation

被引：11

作者：

Griffiths, Rhys C. ^{[1
]}

Smith, Frances R. ^{[1
]}

Li, Diyuan ^{[1
]}

Wyatt, Jasmine ^{[2
]}

Rogers, David M. ^{[1
]}

Long, Jed E.

Cusin, Lola M. L. ^{[3
,4
]}

Tighe, Patrick J. ^{[3
,4
]}

Layfield, Robert

Hirst, Jonathan D. ^{[1
]}

Mueller, Manuel M. ^{[2
]}

Mitchell, Nicholas J. ^{[1
]}

机构：

[1] Univ Nottingham, Sch Chem, Univ Pk, Nottingham NG7 2RD, England

[2] Kings Coll London, Dept Chem, London SE1 1DB, England

[3] Univ Nottingham, Med Sch, Sch Life Sci, Univ Pk, Nottingham NG7 2UH, England

[4] Univ Nottingham, Sch Life Sci, Univ Pk, Nottingham NG7 2RD, England

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2023年 / 29卷 / 16期

基金：

英国惠康基金; 英国工程与自然科学研究理事会;

关键词：

bioconjugation; cysteine; desulfurization; post-translational modifications; site-selective; CHEMISTRY; LIGATION; INSTALLATION; POLYPEPTIDES; EXPANSION;

D O I：

10.1002/chem.202202503

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The site-selective modification of peptides and proteins facilitates the preparation of targeted therapeutic agents and tools to interrogate biochemical pathways. Among the numerous bioconjugation techniques developed to install groups of interest, those that generate C(sp(3))-C(sp(3)) bonds are significantly underrepresented despite affording proteolytically stable, biogenic linkages. Herein, a visible-light-mediated reaction is described that enables the site-selective modification of peptides and proteins via desulfurative C(sp(3))-C(sp(3)) bond formation. The reaction is rapid and high yielding in peptide systems, with comparable translation to proteins. Using this chemistry, a range of moieties is installed into model systems and an effective PTM-mimic is successfully integrated into a recombinantly expressed histone.

引用

页数：8

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