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Updated: Aug 29, 2026

An Inexpensive Adaptation of a Commercial Microwave Reactor for Solid Phase Peptide Synthesis
Published on: November 22, 2024
Organophosphorus and nitro-substituted sulfonate esters of 1-hydroxy-7-azabenzotriazole as highly efficient
Louis A Carpino1, Jusong Xia, Chongwu Zhang
1Department of Chemistry, University of Massachusetts, Amherst, Massachusetts 01003, USA. carpio@chem.umass.edu
Abstract:
Organophosphorus esters 9, 10, 14, and 15 prepared via reaction of diethyl- and diphenylphosphoryl chloride, di(o-tolyl)phosphinyl chloride, and 2,8-dimethylphenoxaphosphinyl chloride with HOAt are excellent coupling reagents for peptide synthesis which are generally superior to their uronium/guanidinium analogues and HOBt- or HODhbt-derived phosphate ester counterparts in minimizing loss of configuration during segment coupling. The phosphinyl analogues are more shelf-stable than the phosphoryl systems. The new reagents have been tested in segment couplings leading to two tripeptides (20, 21) and a hexapeptide 22. Outstanding utility is also shown for the solid-phase assembly of the ACP decapeptide. Similar results were obtained with the 2- and 4-nitro- and 2,4-dinitrophenylsulfonyl esters derived from HOAt.
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