Synthesis of Sulfonated Peptides Using a Trifluoromethyltoluene-Protected Amino AcidClick to copy article linkArticle link copied!
- Ashley E. DeYongAshley E. DeYongDepartment of Surgery, Beth Israel Deaconess Medical Center, Harvard Medical School, Boston, Massachusetts 02215, United StatesMore by Ashley E. DeYong
- Kaicheng LiKaicheng LiDepartment of Surgery, Beth Israel Deaconess Medical Center, Harvard Medical School, Boston, Massachusetts 02215, United StatesMore by Kaicheng Li
- Elliot L. Chaikof*Elliot L. Chaikof*Email: [email protected]. Phone: (617) 632-9581. Fax: (617) 632-9701.Department of Surgery, Beth Israel Deaconess Medical Center, Harvard Medical School, Boston, Massachusetts 02215, United StatesDivision of Health Sciences and Technology, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United StatesBroad Institute of MIT and Harvard, Cambridge, Massachusetts 02142, United StatesMore by Elliot L. Chaikof
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.
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