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Dehydroalanine has emerged in recent years as a non-proteinogenic residue with strong chemical utility in proteins for the study of biology. In this review we cover the several methods now available for its flexible and site-selective incorporation via a variety of complementary chemical and biological techniques and examine its reactivity, allowing both creation of modified protein side-chains through a variety of bond-forming methods (C-S, C-N, C-Se, C-C) and as an activity-based probe in its own right. We illustrate its utility with selected examples of biological and technological discovery and application.

Original publication

DOI

10.1016/j.cbpa.2018.05.022

Type

Journal article

Journal

Curr Opin Chem Biol

Publication Date

10/2018

Volume

46

Pages

71 - 81

Keywords

Alanine, Animals, Biocatalysis, Chemistry Techniques, Synthetic, Humans, Models, Molecular, Protein Processing, Post-Translational, Proteins