Synthesis of disulfide-rich C-terminal Cys-containing peptide acids through a photocleavable side-chain anchoring strategy

Luo, J.; Gao, Y.; Zhao, R.; Shi, J.; Li, Y.-M.

Organic and Biomolecular Chemistry 21(44): 8863-8867

2023


ISSN/ISBN: 1477-0539
PMID: 37888757
Accession: 090686760

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Abstract
A side-chain anchoring strategy has been developed as an effective method for the synthesis of C-terminal Cys-containing peptide acids. However, the application of this strategy to CCAs containing more than one disulfide bond is still hindered due to the trifluoroacetic acid (TFA) lability of the anchored side-chain groups. Herein, we report a photocleavable side-chain anchoring strategy using newly developed molecules having photocleavable side-chain protecting groups that are stable against TFA cleavage to assist in the formation of disulfide bonds. The utility of this new strategy was demonstrated by the synthesis of Riparin 1.1 and hCNP22 containing one disulfide bond and α-conotoxin Vc1.1 containing two disulfide bonds. This new strategy will provide new possibilities for the synthesis of disulfide-rich C-terminal Cys-containing peptide acids.