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

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

Journal Name: Protein & Peptide Letters

Volume 16 , Issue 2 , 2009

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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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Article Details

VOLUME: 16
ISSUE: 2
Year: 2009
Page: [105 - 111]
Pages: 7
DOI: 10.2174/092986609787316270
Price: $65

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