Generic placeholder image

Protein & Peptide Letters

Author(s): Chennakrishnareddy Gundala, Subramanyam J. Tantry, Shankar A. Naik and Vommina Venkata Sureshbabu

DOI: 10.2174/092986609787316270

DownloadDownload PDF Flyer Cite As
Synthesis of 1,1-Dioxobenzo[b]thiophene-2-ylmethyloxycarbonyl (Bsmoc) Protected N-Methyl Amino Acids by Reduction of Bsmoc-5-Oxazolidinones and Their Use in Peptide Synthesis

Page: [105 - 111] Pages: 7

  • * (Excluding Mailing and Handling)

Abstract

The synthesis of Bsmoc-N-methyl amino acids is presented. The first step involves p-toluenesulfonic acid (TsOH) catalysed condensation of a Bsmoc-amino acid with paraformaldehyde to furnish N-Bsmoc-5-oxazolidinone under MW irradiation. This intermediate is reduced to the corresponding N-methyl amino acid using triethylsilane (Et3SiH) and trifluoroacetic acid (TFA) at r.t. The N-methyl amino acids are converted into corresponding acid fluorides using diethylaminosulfur trifluoride (DAST) and employed as coupling agents in the synthesis of dipeptides. The peptide coupling was mediated by KOAt in CH2Cl2.

Keywords: Bsmoc N methyl amino acids, 5-Oxazolidinone, Amino acid fluorides, KOAt