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Synfacts 2023; 19(03): 0319
DOI: 10.1055/s-0042-1753292
Peptide Chemistry

One-Pot Synthesis of N-Methyl Dipeptides from Amino Acid-Derived Oxazolidinones

Contributor(s):
Hisashi Yamamoto
,
Isai Ramakrishna
Dorow RL, *, Gingrich DE. DuPont Pharmaceuticals Company, Wilmington, USA
A Novel, One-Pot Preparation of N-Methyl-α-Amino Acid Dipeptides from Oxazolidinones and Amino Acids.

Tetrahedron Lett. 1999;
40: 467-470
DOI: 10.1016/S0040-4039(98)02426-5.
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Key words

oxazolidinones - N-methyl dipeptides - amino acid esters

Significance

N-Methyl peptides play a crucial role in peptide drug discovery. This N-methyl peptide is especially useful for the improvement of biological properties such as target affinity, proteolytic stability and membrane permeability as well as the alteration of the conformational rigidity and hydrophobicity of the peptides. In 1999, R. L. Dorow and co-workers developed a one-pot synthesis of N-methyl-α-amino acid dipeptides from oxazolidinones and amino acids.


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Comment

A series of amino-acid-derived oxazolidinones reacted smoothly with the amino acid esters to produce N-hydroxymethyl dipeptides, which were treated with TFAA and Et3SiH to produce the corresponding N-methyl dipeptides in good yields. This one-pot protocol is a practically simple and highly efficient method to produce various N-methyl peptides.


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Publication History

Article published online:
13 February 2023

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