124650-79-9

Upstream product

• 4124-76-9 N-(benzyloxycarbonyl)-L-glutamic acid anhydride 
• 81470-51-1 tert-butyl N-benzyloxycarbonyl-L-pyroglutamate 
• 124620-51-5 (S)-tert-butyl 2-(((benzyloxy)carbonyl)amino)-5-hydroxypentanoate 
• 124620-52-6 N²-(benzyloxycarbonyl)-N⁵-(benzyloxy)-N⁵-<(2,2,2-trichloroethoxy)carbonyl>-L-ornithine 1-tert-butyl ester 
• 92412-96-9 N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithine 1-tert-butyl ester 
• 124620-53-7 allyl N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithinate 
• 89969-29-9 N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithine 
• 32159-21-0 Cbz-L-pGlu-OH 
• 5891-45-2 (S)-2-(benzyloxycarbonylamino)pentanedioic acid tert-butyl ester 
• 1155-62-0 N-benzyloxycarbonyl-L-glutamic acid 
• 124620-55-9 N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithine 

Downstream Products

• 130761-77-2 N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-L-seryl-1,4-dibenzyl-D-aspartate 
• 130761-84-1 N⁵-acetyl-N⁵-hydroxy-L-ornithyl-N⁵-acetyl-N⁵-hydroxy-L-ornithyl-N⁵-acetyl-N⁵-hydroxy-L-ornithyl-D-4-hydroxyphenylglycine 
• 130761-74-9 benzyl N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-L-serinate 
• 130761-82-9 benzyl N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-D-4-hydroxyphenylglycinate 
• 124620-56-0 (N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl)-(N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl)-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithine 

Relevant academic research and scientific papers

Synthesis and Siderophore Activity of Albomycin-like Peptides Derived from N5-Acetyl-N5-hydroxy-L-ornithine

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.