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
|
| Links |