148823-30-7Relevant articles and documents
Synthesis of new peptide inhibitors of the meso-diaminopimelate-adding enzyme
Le Roux,Auger,Va Heijenoort,Blanot
, p. 899 - 907 (1992)
In order to obtain inhibitors of the meso-diaminopimelate-adding enzyme, which catalyzes an early reaction in the biosynthesis of bacterial peptidoglycan, several new peptide derivatives of general formula, N(α)-propionyl-L-alanyl-D (or ambo)-Xaa were synthesized: four transition-state analogs (Xaa = phosphinothricin, homocysteic acid, buthionine sulfoximine, buthionine sulfoximine phosphate), three analogs of γ-D-glytamyl phosphate (Xaa = 3-phosphonoacetamideo-alanine, 3-phosphonomethylamino-aspartic acid, 2-amino-6-phosphonohexanoic acid), and one derivative with Xaa = ornithine. After preincubation with partially purified meso-diaminopimelate-adding enzyme from Escherichia coli, peptide derivatives with Xaa - buthionine sulfoximine, 3-phosphonoacetamido-alanine and 2-amino-6-phosphonohexanoic acid appeard to be among the best inhibitors obtained up to date, with I50 values between 0.6 and 1.2 mM. When the two first compounds were tested for in vitro antibacterial activity, they gave negative results.
