Syntheses of 2-[(1S,3S)-1-amino-3-carboxy-3-hydroxypropyl]-thiazole-4-carboxylic acid and the tripeptide skeleton of nosiheptide containing the acid

Article abstract of DOI:10.1246/bcsj.68.3151

The stereoselective synthesis of an amino acid component called Fragment D, N,O-diprotected 2-[(1S,3S)-1-amino-3-carboxy-3-hydroxypropyl]thiazole-4-carboxylic acid of a macrobicyclic peptide antibiotic nosiheptide, was achieved by two routes. The dipeptide, Fragment B-C, 2-[(Z)-1-(N,O-isopropylidene-L-threonylamino)-1-propenyl]thiazole-4-ca rboxylic acid was also synthesized by the thiazole ring formation from (Z)-2-(N,O-diprotected L-threonylamino)-2-butenethioamide with ethyl bromopyruvate. The coupling of two components by using a condensing agent gave the expected tripeptide 2, which is an important partial skeleton of the nosiheptide.