Synthesis of analogs of D-Ala-D-Ala as potential inhibitors of bacterial cell wall biosynthesis.
The syntheses of the L,L- and D,D-stereoisomers of N- phenoxyacetyl -X-alanine in which X = Ser, Ala( beta Cl ) or Arg, are described. The antibacterial activity of these peptides and some of their synthetic intermediates has been examined. Four of the intermediates in which X = Ala( beta Cl ) and Arg(NO2), which possess C-terminal benzyl ester groups, were active against viridans streptococci and Streptococcus agalactiae. The D,D-enantiomers were more active than the corresponding L,L-isomers. None of the compounds were active against beta-lactamase producing bacteria or acted as beta-lactamase inhibitors.
D001419:Bacteria / Q000187:drug effects* / Q000378:metabolism; D002473:Cell Wall / Q000187:drug effects* / Q000378:metabolism; D004151:Dipeptides / Q000138:chemical synthesis* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D013292:Streptococcus agalactiae / Q000187:drug effects
D004151:Dipeptides; C002956:alanylalanine