A Photolabile Carboxyl Protecting Group for Solid Phase Peptide Synthesis

Hongpeng Yang; Tao Peng; Xiaoxue Wen; Tingting Chen; Yunbo Sun; Shuchen Liu; Gang Wang; Shouguo Zhang; Lin Wang

doi:10.1002/open.202000324

A Photolabile Carboxyl Protecting Group for Solid Phase Peptide Synthesis

ChemistryOpen. 2021 Apr;10(4):497-502. doi: 10.1002/open.202000324.

Authors

Hongpeng Yang^{1

2}, Tao Peng², Xiaoxue Wen², Tingting Chen², Yunbo Sun², Shuchen Liu², Gang Wang², Shouguo Zhang², Lin Wang^{1

2}

Affiliations

¹ Faculty of Environment & Life, Beijing University of Technology, Beijing, 100124, China.
² Beijing Institute of Radiation Medicine, 27 Taiping Road, Haidian District, Beijing, 100850, China.

Abstract

A new kind of photolabile protecting group (PLPG) for carboxyl moieties was designed and synthesized as the linker between resin and peptide. This group can be used for the protection of amino acid carboxyl groups. The peptide was synthesized on Nph (2-hydroxy-3-(2-nitrophenyl)-heptanoic acid)-derivatized resins and could be cleaved under UV exposure, thus avoiding the necessity for harsh acid-mediated resin cleavage. The PLPG has been successfully used for solid-phase synthesis of peptides.

Keywords: linker molecules; peptides; photolabile compounds; protecting groups; solid-phase synthesis.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Heptanoic Acids / chemistry*
Heptanoic Acids / radiation effects
Nitrobenzenes / chemistry*
Nitrobenzenes / radiation effects
Peptides / chemical synthesis*
Solid-Phase Synthesis Techniques / methods
Ultraviolet Rays

Substances

Heptanoic Acids
Nitrobenzenes
Peptides