Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Selective Chemical Cleavage of Threonine Peptides
Takeo KanekoShoichi KusumotoToshishige InuiTetsuo Shiba
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1968 Volume 41 Issue 9 Pages 2155-2161

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Abstract

Threonine peptide was converted to an oxazolidone derivative via an O-chlorocarbonyl derivative by treatment with phosgene and dimethylaniline followed by refluxing in xylene, wherever the threonine residue was located in peptide chain, that is, either at amino or carboxyl terminal, or in the middle of the chain. When the oxazolidone peptide was treated with alkali at room temperature, the peptide bond of the original threonine residue of which the amino group participated was selectively cleaved giving a mixture of the carboxylic acid derived from the N-terminal amino acid or peptide, and 5-methyl-2-oxo-oxazolidine-4-carbonyl derivative, whereas other peptide bonds remained unchanged in this reaction. Several threonine peptides were synthesized and were subjected to the cleavage reaction. In all cases the expected cleavage occurred in a satisfactory yield.

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