3588-60-1

Basic information

• Product Name: N-CARBOBENZOXY-DL-LEUCINE
• Synonyms: 2-[[(BENZYLOXY)CARBONYL]AMINO]-4-METHYLPENTANOIC ACID;CARBOBENZYLOXY-DL-LEUCINE;CARBOBENZOXY-DL-LEUCINE;N-CBZ-DL-LEUCINE;N-CARBOBENZOXY-DL-LEUCINE;N-ALPHA-CARBOBENZOXY-DL-LEUCINE;Z-DL-LEUCINE;Z-DL-LEU-OH
• CAS NO: 3588-60-1
• Molecular Formula: C₁₄H₁₉NO₄
• Molecular Weight: 265.3
• EINECS: 206-759-6
• Product Categories: Amino Acids;Amino Acids (N-Protected);Biochemistry;Cbz-Amino Acids
• Mol File: 3588-60-1.mol
• Article Data: 14

Chemical Properties

• Melting Point: 54 °C
• Boiling Point: 442.8 °C at 760 mmHg
• Flash Point: 221.6 °C
• Appearance: White or colorless powder
• Density: 1.158 g/cm³
• Storage Temp.: 2-8°C
• Solubility: Acetonitrile (Slightly), Chloroform (Slightly), DMSO (Slightly), Ethanol (Slight
• PKA: 4.00±0.21(Predicted)
• BRN: 4695869
• CAS DataBase Reference: N-CARBOBENZOXY-DL-LEUCINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-CARBOBENZOXY-DL-LEUCINE(3588-60-1)
• EPA Substance Registry System: N-CARBOBENZOXY-DL-LEUCINE(3588-60-1)

Safety Data

• Safety Statements: S24/25:Avoid contact with skin and eyes.
• WGK Germany: 3
• Hazardous Substances Data: 3588-60-1(Hazardous Substances Data)

Usage

Description

It is a biologically active amino acid usually used as nutritional supplements, flavour enhancer, and components for preparing pharmaceutical and biochemical products such as amino acid infusion and comprehensive amino acid, hypoglycemic agent, plant growth promoter. Specifically, it is found that ingestion of a high whey protein, leucine-enriched supplement resulted in a larger overall postprandial muscle protein synthesis rate in healthy older people compared with a conventional dairy product.1 Moreover, this substance possesses the most marked anabolic characteristics in acting as a trigger element for the initiation of protein synthesis, thus guaranteeing the healthy human skeleton muscle metabolism.2 In addition, this chemical may be involved in the promotion of plant growth.3

Reference

Luiking, Y. C.; Deutz, N. E. P.; Memelink, R. G.; Verlaan, S.; Wolfe, R. R., Postprandial muscle protein synthesis is higher after a high whey protein, leucine-enriched supplement than after a dairy-like product in healthy older people: a randomized controlled trial. Nutr. J. 2014, 13, 14. Wilkinson, D. J.; Hossain, T.; Hill, D. S.; Phillips, B. E.; Crossland, H.; Williams, J.; Loughna, P.; Churchward-Venne, T. A.; Breen, L.; Phillips, S. M.; Etheridge, T.; Rathmacher, J. A.; Smith, K.; Szewczyk, N. J.; Atherton, P. J., Effects of leucine and its metabolite -hydroxy--methylbutyrate on human skeletal muscle protein metabolism. J. Physiol.-London 2013, 591, 2911-2923. Glick, B. R.; Todorovic, B.; Czarny, J.; Cheng, Z. Y.; Duan, J.; McConkey, B., Promotion of plant growth by bacterial ACC deaminase. Crit. Rev. Plant Sci. 2007, 26, 227-242.

Chemical Properties

White powder

Upstream product

• 91806-74-5 3,5-dimethyl-pyrazole-1-carboxylic acid benzyl ester 
• 328-39-2 LEUCINE 
• 501-53-1 benzyl chloroformate 
• 100-51-6 benzyl alcohol 
• 26054-60-4 ((S)-2-Oxo-oxetan-3-yl)-carbamic acid benzyl ester 
• 1068-55-9 isopropylmagnesium chloride 
• 127862-69-5 2-Benzyloxycarbonylamino-4-methyl-pentanoic acid 2,2,2-trifluoro-ethyl ester 
• 204922-63-4 2-Benzyloxycarbonylamino-4-methyl-4-nitro-pentanoic acid methyl ester 
• 687-51-4 H-L-Leu-NH₂ 
• 19506-72-0 benzyl-8-quinolyl carbonate 

Downstream Products

• 122272-76-8 (N-benzyloxycarbonyl-leucyl)-phosphoric acid dibenzyl ester 
• 55387-20-7 N-(N-benzyloxycarbonyl-DL-leucyl)-N'-isonicotinoyl-hydrazine 
• 28862-79-5 Z-D-Leu-OH 
• 21931-02-2 (S)-benzyl 4-methyl-1-oxo-1-(phenylamino)pentan-2-ylcarbamate 
• 18869-43-7 DL-leucine methyl ester 
• 93997-21-8 DL-N-Carbobenzoxy-leucin-bis-(2-chloraethyl)-amid 
• 93147-02-5 [1-(2-Chloro-ethylcarbamoyl)-3-methyl-butyl]-carbamic acid benzyl ester 
• 119805-68-4 {1-[4-(6-Dimethylamino-purin-9-ylmethyl)-phenylcarbamoyl]-3-methyl-butyl}-carbamic acid benzyl ester 
• 132246-11-8 (1-Hydroxy-3-methyl-butyl)-carbamic acid benzyl ester 
• 132246-10-7 Acetic acid 1-benzyloxycarbonylamino-3-methyl-butyl ester 
• 49761-04-8 (S)-1-(2-Benzyloxycarbonylamino-4-methyl-pentanoyl)-pyrrolidine-2-carboxylic acid methyl ester 
• 49761-04-8 (S)-1-(2-Benzyloxycarbonylamino-4-methyl-pentanoyl)-pyrrolidine-2-carboxylic acid methyl ester 
• 2018-66-8 Z-Leu-OH 
• 70853-26-8 O-benzyl-N-(4-methyl-1-oxopentan-2-yl)carbamid acid 

Relevant articles and documents

Chiral tetraaryl-and tetraalkynylborates as chiral solvating agents for tetraalkylammonium salts

The application of tetracarbon-substituted chiral borate sodium salts (NaBR*4) as NMR chiral solvating agents for various tetraalkylammonium salts (R4NX) has been successfully demonstrated. Ion exchange between R4NX and NaBR*4 proceeded in excellent yields and provided the corresponding dia-stereomeric salts (R4NBR*4). The ee values of the R4NX salts were determined by1H NMR analysis of R4NBR*4. Two types of chiral borates, tetraaryl-and tetraalkynylborates with optically active 1,1′-binaphthyl components were used. At the beginning of this research, we investigated the efficacy of a known chiral tetraar-ylborate developed by Pommerening et al. for R4NX. To expand the possibility of further structural design of the chiral borate, we designed chiral tetraalkynylborates as a new structure. Their synthesis and application are also described.

Synthesis, screening and docking of small heterocycles as Glycogen Phosphorylase inhibitors

A series of morpholine substituted amino acids (phenylalanine, leucine, lysine and glutamic acid) was synthesized. A fragment-based screening approach was then used to evaluate a series of small heterocycles, including morpholine, oxazoline, dihydro-1,3-oxazine, tetrahydro-1,3-oxazepine, thiazoline, tetrahydro-1,3-pyrimidine, tetrahydro-1,3-diazepine and hexahydro-1H-benzimidazole, as potential inhibitors of Glycogen Phosphorylase a. Thiazoline 7 displayed an improved potency (IC50 of 25 μM) and had good LE and LELP values, as compared to heterocycles 1, 5, 9e13 and 19 (IC50 values of 1.1 mM e23.9 mM). A docking study using the crystal structure of human liver Glycogen Phosphorylase, provided insight into the interactions of heterocycles 5, 7, 9e13 and 19 with Glycogen Phosphorylase.

A Stereoselective entry into functionalized 1,2-diamines by zinc-mediated homologation of α-aminoacids

A general, stereoselective synthsis of 4,5-disubstituted imidazolidines-2-ones from α-aminoacids has been developed: the key steps are a Biaise reaction of bromoacetate on α-aminonitriles and further reduction. Although reduction with sodium cyanoborohydride afforded a mixture of cis and trans isomers 6a-e with moderate to good stereoselectivity, reduction with sodium in liquid ammonia gave the trans isomers 8a-e with complete stereoselectivity. Acidic hydrolysis of the urea gave 4-amino-pyrrolidinones, which can be precursors to β,γ-diaminoacids or 3-aminopyrrolidines.