Synthesis of Sulfonated Peptides Using a Trifluoromethyltoluene-Protected Amino Acid.

The Journal of organic chemistry
Authors
Abstract

A scalable, seven step synthesis is reported for a trifluoromethyl toluene protected sulfonated phenylalanine building block whose utility was demonstrated in the synthesis of four CXCR4-derived sulfonopeptides. When compared to a conventional trichloroethyl protected building block, overall yield was improved by up to 4-fold. We believe this building block will prove to be of significant value for the synthesis of a variety of peptide targets containing phenylalanine sulfonate, a bioisostere of tyrosine sulfate, enabling orthogonal protection strategies and improving synthetic efficiency and yield.

Year of Publication
2025
Journal
The Journal of organic chemistry
Date Published
01/2025
ISSN
1520-6904
DOI
10.1021/acs.joc.4c02529
PubMed ID
39809455
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