Dmpic as an Orthogonal Protecting Group for Aspartic Acid Side Chains: Facilitating the Synthesis of Lactam-Cyclized Peptides

The Journal of Organic Chemistry 2026

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Authors: Bin Liu, Hanxi Bai, Farong Ye, Kommuru Goutham, Dalovai Purnachandar, Chanjuan Liu, Ping Huang, Ping Wang
DOI: 10.1021/acs.joc.6c00442
Cited by: 1
References: 38

Abstract

Orthogonal protection of the Asp side chain is critical in peptide synthesis. We introduce the 2-pyridyl isopropyl (Dmpic) group as a photolabile protecting group for the Asp side-chain carboxyl functionality. Dmpic demonstrates excellent stability under both strongly acidic and basic conditions, effectively suppresses aspartimide formation, and can be removed under mild conditions, facilitating the efficient synthesis of diverse Asp-containing lactam-cyclized peptides. Moreover, Dmpic exhibits excellent orthogonality with common protecting groups, offering a straightforward strategy for the synthesis of Asp-containing lactam-cyclized peptides.

Fields of Study & Subjects

Chemical Synthesis and Analysis Photochromic and Fluorescence Chemistry Click Chemistry and Applications

Publication details

Journal / source
The Journal of Organic Chemistry
Publisher
American Chemical Society (ACS)
Volume
91
Issue
19
Pages
6724–6731
Publication date
30 April 2026
Language
EN