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

Chennakrishnareddy      Gundala; Subramanyam   J.   Tantry; Shankar   A.   Naik; Vommina   Venkata   Sureshbabu

doi:10.2174/092986609787316270

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

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Protein & Peptide Letters

Title: 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

Volume: 16 Issue: 2

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

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

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.

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Gundala Chennakrishnareddy, Tantry J. Subramanyam, Naik A. Shankar and Sureshbabu Venkata Vommina, 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, Protein & Peptide Letters 2009; 16 (2) . https://dx.doi.org/10.2174/092986609787316270