92412-96-9

Basic information

• Product Name: N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithine 1-tert-butyl ester
• Synonyms: N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithine 1-tert-butyl ester
• CAS NO: 92412-96-9
• Molecular Weight: 470.566
• Mol File: 92412-96-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithine 1-tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithine 1-tert-butyl ester(92412-96-9)
• EPA Substance Registry System: N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithine 1-tert-butyl ester(92412-96-9)

Safety Data

• Hazardous Substances Data: 92412-96-9(Hazardous Substances Data)

Upstream product

• 81470-51-1 tert-butyl N-benzyloxycarbonyl-L-pyroglutamate 
• 124620-51-5 (S)-tert-butyl 2-(((benzyloxy)carbonyl)amino)-5-hydroxypentanoate 
• 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 
• 34582-33-7 α-tert-butyl-γ-methyl L-Glu diester hydrochloride 
• 92412-88-9 N⁵-Acetyl-N²,N²-diallyl-N⁵-benzyloxy-L-ornithin-tert-butylester 
• 92412-92-5 tert-Butyl-<5-(benzyloxyimino)-2-(diallylamino)valerat> 
• 92412-93-6 N²,N²-Diallyl-N⁵-benzyloxy-L-ornithin-tert-butylester 
• 92412-89-0 N²,N²-Diallyl-L-glutaminsaeure-1-tert-butyl-5-methylester 
• 92412-90-3 tert-Butyl-<2-(diallylamino)-5-hydroxyvalerat> 
• 92412-91-4 tert-Butyl-<2-(diallylamino)-4-formylbutyrat> 
• 2687-43-6 O-benzylhydoxylamine hydrochloride 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 124620-55-9 N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithine 
• 124620-54-8 allyl N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithinate 
• 124620-56-0 (N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl)-(N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl)-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithine 
• 124650-79-9 Allyl N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithinate 
• 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 
• 130761-72-7 benzyl N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithinate 
• 130761-71-6 allyl N²-(3,5-dinitrobenzoyl)-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithinate 
• 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 
• 89969-29-9 N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithine 

Relevant articles and documents

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.

Albomycins, III. - Synthesis of N5-acetyl-N5-hydroxy-L-ornithine from L-glutamic acid

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