A new synthetic pathway to preparation of selectively thionated peptides will be described. The new method uses thiophosphoramidate synthons containing a methyl ester of an amino acid. When these are coupled with boc-protected di- or tripeptides a thiophosphoryl carbonyl mixed imide is formed. This rearranges to a phosphoryl thiocarbonyl mixed imide where only one amino acid has a sulfur. This compound is easily cleaved in mild conditions to form a pseudopeptide with potential activity against viral agents.

Preparation of pseudotripeptides from novel rearrangement of mixed imides of thiophosphoryl carbonyl compounds to phosphoryl thiocarbonyl compounds

239th National Meeting (2010)

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