Synthesis of β-Thiol Phenylalanine for Applications in One-Pot Ligation-Desulfurization Chemistry

Lara R Malins; Andrew M Giltrap; Luke J Dowman; Richard J Payne

doi:10.1021/acs.orglett.5b00597

Synthesis of β-Thiol Phenylalanine for Applications in One-Pot Ligation-Desulfurization Chemistry

Org Lett. 2015 May 1;17(9):2070-3. doi: 10.1021/acs.orglett.5b00597. Epub 2015 Apr 10.

Authors

Lara R Malins¹, Andrew M Giltrap¹, Luke J Dowman¹, Richard J Payne¹

Affiliation

¹ School of Chemistry, The University of Sydney, New South Wales, 2006, Australia.

PMID: 25860301
DOI: 10.1021/acs.orglett.5b00597

Abstract

The efficient synthesis of a β-thiol phenylalanine derivative is described starting from Garner's aldehyde. The utility of this amino acid in peptide ligation-desulfurization chemistry is described, including the trifluoroethanethiol (TFET)-promoted one-pot assembly of the 62 residue peptide hormone augurin.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aldehydes / chemistry
Ligation
Molecular Structure
Neoplasm Proteins / chemistry
Peptide Hormones / chemistry
Peptides / chemistry
Phenylalanine / analogs & derivatives*
Phenylalanine / chemical synthesis*
Phenylalanine / chemistry
Sulfhydryl Compounds / chemical synthesis*
Sulfhydryl Compounds / chemistry
Trifluoroethanol / analogs & derivatives
Trifluoroethanol / chemistry
Tumor Suppressor Proteins

Substances

2,2,2-trifluoroethanethiol
Aldehydes
ECRG4 protein, human
Neoplasm Proteins
Peptide Hormones
Peptides
Sulfhydryl Compounds
Tumor Suppressor Proteins
Phenylalanine
Trifluoroethanol