Synthesis and siderophore activity of albomycin-like peptides derived from N5-acetyl-N5-hydroxy-L-ornithine

EK Dolence, CE Lin, MJ Miller…

Index: Dolence, E. Kurt; Lin, Chia-En; Miller, Marvin J.; Payne, Shelley M. Journal of Medicinal Chemistry, 1991 ,  vol. 34,  # 3  p. 956 - 968

Full Text: HTML

Citation Number: 38

Abstract

N6-Acetyl-P-hydroxyL-ornithine (l), the key constituent of several microbial siderophores, has been synthesized in 23% yield overall from N-Cbz-L-glutamic acid 1-tert-butyl ester (6) derived from L-glutamic acid. Reduction of 6 to 7 and treatment with N-[(trichloroethoxy) carbonyl]-0-benzylhydroxylamine (8), and diethyl azodicartmxylate and triphenylphosphine followed by deprotection produced the protected M-acetyl-N6-hydroxy-L-omithme ...