89969-29-9Relevant articles and documents
Synthesis and Siderophore Activity of Albomycin-like Peptides Derived from N5-Acetyl-N5-hydroxy-L-ornithine
Dolence, E. Kurt,Lin, Chia-En,Miller, Marvin J.,Payne, Shelley M.
, p. 956 - 968 (2007/10/02)
N5-Acetyl-N5-hydroxy-L-ornithine (1), the key constituent of several microbial siderophores, has been synthesized in 23percent 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>-O-benzylhydroxylamine (8), and diethyl azodicarboxylate and triphenylphosphine followed by deprotection produced the protected N5-acetyl-N5-hydroxy-L-ornithine derivatives 11 and 12 in large quantities (10-20 g).Following α-amino and α-carboxyl deprotections of 11 and 12, EEDQ mediated peptide coupling and final deprotection provided amino acid 1 and six albomycin-like peptides (20, 23, 25, 28, 35, and 36).The growth-promoting ability of each was evaluated with the siderophore biosynthesis mutant Shigella flexneri SA240 (SA 100 iucD:Tn5).These results indicate that substantial modification of the framework of peptide-based siderophores can be tolerated by microbial iron-transport systems.
CONSTITUENTS OF MICROBIAL IRON CHELATORS. THE SYNTHESIS OF OPTICALLY ACTIVE DERIVATIVES OF δ-N-HYDROXY-L-ORNITHINE.
Lee, Byung Hyun,Miller, Marvin J.
, p. 927 - 930 (2007/10/02)
δ-N-Hydroxy-L-ornithine derivatives were synthesized from L-glutamic acid by reduction of the γ-acid chloride to the aldehyde, formation of the substituted oxime, and reductive acylation
