21691-43-0

Basic information

• Product Name: N-CARBOBENZOXY-DL-NORVALINE
• Synonyms: Z-DL-APE(2)-OH;Z-DL-2-AMINOVALERIC ACID;Z-DL-NHCH[CH3(CH2)2]-COOH;Z-DL-NORVALINE;Z-DL-NVA-OH;N-ALPHA-CARBOBENZOXY-DL-NORVALINE;N-ALPHA-CARBOBENZOXY-DL-2-AMINO-PENTANOIC ACID;Carbobenzoxynorvaline
• CAS NO: 21691-43-0
• Molecular Formula: C₁₃H₁₇NO₄
• Molecular Weight: 251.28
• Product Categories: Amino Acids;Amino Acids (N-Protected);Biochemistry;Cbz-Amino Acids
• Mol File: 21691-43-0.mol

Chemical Properties

• Melting Point: 88 °C
• Boiling Point: 439.4°Cat760mmHg
• Flash Point: 219.6°C
• Appearance: Off-white to white/Powder
• Density: 1.184g/cm³
• Vapor Pressure: 1.69E-08mmHg at 25°C
• Refractive Index: 1.533
• Solubility: almost transparency in Methanol
• CAS DataBase Reference: N-CARBOBENZOXY-DL-NORVALINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-CARBOBENZOXY-DL-NORVALINE(21691-43-0)
• EPA Substance Registry System: N-CARBOBENZOXY-DL-NORVALINE(21691-43-0)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 21691-43-0(Hazardous Substances Data)

Usage

Chemical Properties

White powder

InChI:InChI=1/C13H17NO4/c1-2-6-11(12(15)16)14-13(17)18-9-10-7-4-3-5-8-10/h3-5,7-8,11H,2,6,9H2,1H3,(H,14,17)(H,15,16)

Upstream product

• 760-78-1 2-aminopentanoic acid 
• 501-53-1 benzyl chloroformate 
• 127862-67-3 N-benzyloxycarbonyl-DL-norvaline 2,2,2-trifluoroethyl ester 

Downstream Products

• 42918-89-8 (R)-2-(N-benzyloxycarbonylamino)pentanoic acid 
• 117402-83-2 (S)-ethyl 2-(benzyloxycarbonylamino)pentanoate 
• 98980-64-4 Benzyloxycarbonyl-DL-norvalin-seleno-phenylester 
• 178904-00-2 [1-(5-Carbamoyl-3H-[1,2,3]triazol-4-ylcarbamoyl)-butyl]-carbamic acid benzyl ester 
• 114264-10-7 benzyl 1-(diethoxyphosphoryl)butylcarbamate 
• 129960-71-0 benzyl N-[1-(dimethoxyphosphoryl)butyl]carbamate 
• 92235-12-6 Z-DL-Norval-Gly-OC₂H₅ 
• 220953-41-3 4-N-<2-bromo-4-(1-methylethyl)phenyl>-6-<1-(N,N-dimethylcarboxamido)butylamino>-2-methyl-5-nitropyrimidin-4-amine 
• 220953-42-4 4-N-<2-bromo-4-(1-methylethyl)phenyl>-6-<1-(N,N-dimethylamino)-2-pentylamino>-2-methyl-5-nitropyrimidine-4-amine 
• 220953-48-0 4-N-<2-bromo-4-(1-methylethyl)phenyl>-6-<1-(N,N-dimethylamino)-2-pentylamino>-2-methylpyrimidine-4,5-diamine 
• 197803-19-3 D,L-norvaline dimethylamide 

Relevant articles and documents

Primary amino acid derivatives: Compounds with anticonvulsant and neuropathic pain protection activities

Pharmacological management remains the primary method to treat epilepsy and neuropathic pain. We have advanced a novel class of anticonvulsants termed functionalized amino acids (FAAs). In this study, we examine FAA derivatives from which the terminal acetyl moiety was removed and termed these compounds primary amino acid derivatives (PAADs). Twenty-seven PAADs were prepared; the central C(2) R-substituent was varied, including C(2) stereochemistry, and the compounds were tested in rodent models of seizures and neuropathic pain. C(2)-Hydrocarbon N-benzylamide PAADs were potent anticonvulsants and excellent anticonvulsant activity (mice, ip; rat, po) was observed for C(2) R-substituted PAADs in which the R group was ethyl, isopropyl, or tert-butyl, and the C(2) stereochemistry conformed to the d-amino acid configuration ((R)-stereoisomer). These values surpassed the activities of several clinical antiepileptic drugs. The C(2) (R)-ethyl and C(2) (R)-isopropyl PAADs also displayed excellent activities in the mouse (ip) formalin neuropathic pain model. Significantly, unlike the FAA structure-activity relationship, PAAD anticonvulsant activity increased upon substitution of a methylene unit for a heteroatom in the R-substituent that was one atom removed from the C(2) site, suggesting that these PAADs function by a different pathway than FAAs.

Resolution of non-proteinogenic amino acids via microbial lipase-catalyzed enantioselective transesterification

A number of non-proteinogenic amino acids bearing aliphatic side chains were resolved with moderate to good enantioselectivities (E = 15-42) through the Burkholderia cepacia lipase-catalyzed enantioselective transesterification of the 2,2,2-trifluoroethyl esters of their N-benzyloxycarbonyl derivatives with methanol as a nucleophile in diisopropyl ether.

Resolution of non-protein amino acids via Carica papaya lipase-catalyzed enantioselective transesterification

Carica papaya lipase-catalyzed transesterification of the 2,2,2-trifluoroethyl esters of N-benzyloxycarbonylated dl-amino acids carrying aliphatic side chains proceeded smoothly and, in almost all the cases, enantiospecifically (E = >200), affording the l-methyl esters and leaving the d-trifluoroethyl esters intact.

Enantioselective synthesis and absolute configuration of (-)-1-(benzofuran-2-yl)-2-propylaminopentane, ((-)-BPAP), a highly potent and selective catecholaminergic activity enhancer

Enantioselective synthesis and absolute configuration of (-)-1-(benzofuran-2-yl)-2-propylaminopentane ((-)-BPAP), which is a highly potent and selective catecholaminergic activity enhancer (CAE) substance, are described. The synthetic approach consists of the coupling reaction of benzofuran with (R)-N-tosyl-2-propylazirizine or (R)-N-methoxy-N-methylnorvaliamide, followed by appropriate modifications of the resulting coupling products. As the results, (-)-BPAP turned out to have the R configuration, which was finally confirmed by X-ray crystallographic analysis.

Porcine Pancreatic Lipase Catalyzed Enantioselective Hydrolysis of Esters of N-Protected Unusual Amino Acids

Porcine pancreatic lipase catalyzed the highly enantioselective hydrolysis of a kind of α-substituted carboxylic esters, i.e., the 2,2,2-trifluoroethyl esters of the N-benzyloxycarbonyl derivatives of unusual amino acids.

Composition containing a penem or carbapenem antibiotic and the use of the same

Administration of an N-acylated amino acid in association with a penem or carbapenem antibiotic relieves or eliminates the renal problems associated with administration of the antibiotic alone. The amino acid derivative and antibiotic may be formulated together as a composition or administered separately, either simultaneously or sequentially.

Composition containing a penem or carbapenem antibiotic

Administration of an N-acylated amino acid in association with a penem or carbapenem antibiotic relieves or eliminates the renal problems associated with administration of the antibiotic alone. The amino acid derivative and antibiotic may be formulated together as a composition or administered separately, either simultaneously or sequentially. The composition may be prepared by simple mixing.