53054-01-6

Basic information

• Product Name: (S)-2-amino-5-(((benzyloxy)carbonyl)amino)pentanoic acid tert-butyl ester
• Synonyms: (S)-2-amino-5-(((benzyloxy)carbonyl)amino)pentanoic acid tert-butyl ester
• CAS NO: 53054-01-6
• Molecular Weight: 322.404
• Mol File: 53054-01-6.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (S)-2-amino-5-(((benzyloxy)carbonyl)amino)pentanoic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-amino-5-(((benzyloxy)carbonyl)amino)pentanoic acid tert-butyl ester(53054-01-6)
• EPA Substance Registry System: (S)-2-amino-5-(((benzyloxy)carbonyl)amino)pentanoic acid tert-butyl ester(53054-01-6)

Safety Data

• Hazardous Substances Data: 53054-01-6(Hazardous Substances Data)

Upstream product

• 540-88-5 acetic acid tert-butyl ester 
• 3304-51-6 N-carboxybenzyl-L-ornithine 
• 501-53-1 benzyl chloroformate 
• 3184-13-2 L-ornithine hydrochloride 
• 53054-02-7 N_α-(1,1-dimethylethoxycarbonyl)-N_δ-(phenylmethoxycarbonyl)-L-ornithine 1,1-dimethylethyl ester 
• 115-11-7 isobutene 

Downstream Products

• 53054-03-8 tert-butyl (2S)-5-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate 
• 133565-49-8 N_α-(1,1-dimethylethoxycarbonyl)-N_δ-aminothiocarbonylornithine 1,1-dimethylethyl ester 
• 1407512-89-3 (S)-di-tert-butyl 2,2'-((5-((4-((2-(((benzyloxy)carbonyl)amino)ethyl)amino)-6-(octadecylamino)-1,3,5-triazin-2-yl)amino)-1-(tert-butoxy)-1-oxopentan-2-yl)azanediyl)diacetate? 
• 1175686-41-5 (S)-di-tert-butyl 2,2'-((5-(((benzyloxy)carbonyl)amino)-1-(tert-butoxy)-1-oxopentan-2-yl)azanediyl)diacetate 
• 1350629-61-6 (S)-tert-butyloxycarbonylalanyl-(S)-(Nδ-benzyloxycarbonyl)ornithine tert-butyl ester 
• 53054-07-2 L-NOHA 
• 80407-73-4 N^α-(4-amino-4-deoxy-N¹⁰-methylpteroyl)-L-ornithine 
• 96846-20-7 N^α-(4-amino-4-deoxy-N¹⁰-methylpteroyl)-L-ornithine trifluoroacetate 
• 80407-74-5 N^α-(4-amino-4-deoxy-N¹⁰-methylpteroyl)-N^δ-carbobenzoxy-L-ornithine 
• 133565-48-7 N^ω-Hydroxy-L-arginine dihydrochloride 
• 656248-77-0 5-benzyloxycarbonylamino-2-[2-(6-octyl-1,3,5,7-tetraoxo-3,5,6,7-tetrahydro-1H-pyrrolo[3,4-f]isoindol-2-yl)-acetylamino]-pentanoic acid tert-butyl ester 
• 53054-02-7 N_α-(1,1-dimethylethoxycarbonyl)-N_δ-(phenylmethoxycarbonyl)-L-ornithine 1,1-dimethylethyl ester 
• 80407-76-7 N^α-(4-amino-4-deoxy-N¹⁰-methylpteroyl)-N^δ-carbobenzoxy-L-ornithine tert-butyl ester 

Relevant articles and documents

Synthesis and bioactivity of N(ω)-hydroxyarginine: A possible intermediate in the biosynthesis of nitric oxide from arginine [1]

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Dynamic interface imprinting: High-affinity peptide binding sites assembled by analyte-induced recruiting of membrane receptors

Come together: Dynamic molecular recognition events at biological membrane receptors play a key role in cell signaling. Artificial membranes have been prepared with embedded synthetic receptors which dynamically arrange and selectively respond to external stimuli, such as, small peptide ligands. Copyright

Heterocyclic analogues of L-citrulline as inhibitors of the isoforms of nitric oxide synthase (NOS) and identification of N(δ)-(4,5-dihydrothiazol-2-yl)ornithine as a potent inhibitor

L-Thiocitrulline is a known potent inhibitor of several isoforms of nitric oxide synthase (NOS). To explore the structure-activity relationships (SARs) for this molecule in more depth than has previously been reported, three analogues substituted at the sulphur of the isothioureas have been synthesised. In two of these, the S-substituent was 'tied back' sterically by cyclisation to the nitrogen remote from the amino-acid unit. N(δ)-(4,5-Dihydrothiazol-2-yl)ornithine was identified as an inhibitor of rat inducible and constitutive isoforms of NOS and of a constitutive NOS derived from a human tumour xenograft. Analogous N(δ)-(thiazol-2-yl)ornithines were less active, whereas the corresponding N(δ)-(oxazol-2-yl)ornithine and N(δ)-(pyrimidin-2-yl)ornithine failed completely to inhibit NOS. A new efficient preparation of the critical synthetic intermediate, N(α)-Boc-thiocitrulline t-butyl ester, has been developed. Further exploration of the SAR with 2-amino-5-(heterocyclylthio)pentanoic acids (synthesised from 2-(Boc-amino)-5-bromopentanoic acid t-butyl ester), with N-(4-aminobutyl)thiourea and with 2-(4-aminobutylamino)-4,5-dihydrothiazole enabled refinement of our previous model for binding of the substrate, L-arginine, and the inhibitors to NOS.