3588-60-1

Usage

Uses

Used in Nutritional Supplements:
N-CARBOBENZOXY-DL-LEUCINE is used as a nutritional supplement to support muscle protein synthesis and overall muscle health, particularly in older individuals.
Used in Pharmaceutical and Biochemical Products:
N-CARBOBENZOXY-DL-LEUCINE is used as a component in the preparation of amino acid infusions and comprehensive amino acid solutions, which are essential for various medical applications.
Used in Hypoglycemic Agents:
This amino acid is utilized in the development of hypoglycemic agents, which help regulate blood sugar levels in individuals with diabetes.
Used in Plant Growth Promotion:
N-CARBOBENZOXY-DL-LEUCINE is used as a plant growth promoter, potentially enhancing plant growth and development.
Used in Flavor Enhancement:
This amino acid is also employed as a flavor enhancer in the food industry, improving the taste and overall sensory experience of certain products.

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.

Upstream product

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

Downstream Products

• 4108-19-4 D(L)-Z-Leu-PNP 
• 122272-76-8 (N-benzyloxycarbonyl-leucyl)-phosphoric acid dibenzyl ester 
• 55387-20-7 N-(N-benzyloxycarbonyl-DL-leucyl)-N'-isonicotinoyl-hydrazine 
• 4821-82-3 N-benzyloxycarbonyl-DL-leucine cyanomethyl 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 
• 21931-02-2 (S)-benzyl 4-methyl-1-oxo-1-(phenylamino)pentan-2-ylcarbamate 
• 127862-69-5 2-Benzyloxycarbonylamino-4-methyl-pentanoic acid 2,2,2-trifluoro-ethyl ester 
• 33042-97-6 Z-DL-Leu-NH₂ 
• 615-82-7 DL-Leucyl-glycin 
• 5276-79-9 Benzyloxycarbonyl-DL-leucyl-glycyl-glycin-ethylester 
• 252351-90-9 N-benzyloxycarbonyl-leucyl-glycine 
• 123754-61-0 N-benzyloxycarbonyl-glycyl=>valyl=>-thioleucine S-phenyl ester 

Relevant academic research and scientific papers

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 and evaluation of chirally defined side chain variants of 7-chloro-4-aminoquinoline to overcome drug resistance in malaria chemotherapy

A novel 4-aminoquinoline derivative [(S)-7-chloro-N-(4-methyl-1-(4-methyl-piperazin-1-yl)pentan-2-yl)-quinolin-4-amine triphosphate] exhibiting curative activity against chloroquine-resistant malaria parasites has been identified for preclinical development as a blood schizonticidal agent. The lead molecule selected after detailed structure-activity relationship (SAR) studies has good solid-state properties and promising activity against in vitro and in vivo experimental malaria models. The in vitro absorption, distribution, metabolism, and excretion (ADME) parameters indicate a favorable drug-like profile.

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.

Synthesis of enantiopure free and N-benzyloxycarbonyl-protected 3-substituted homotaurines from naturally occurring amino acids

Enantiopure N-benzyloxycarbonyl-protected and free 3-substituted homotaurines were synthesized from naturally occurring amino acids via N-benzyloxycarbonyl protection, Arndt-Eistert homologation, reduction, esterification with thioacetic acid, and oxidation with performic acid. The current method is a convenient, practical, and salt-free method for the synthesis of enantiopure 3-substituted homotaurine with moderate to good yields.

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.

α-Chymotrypsin-catalyzed peptide synthesis in frozen aqueous solution using N-protected amino acid carbamoylmethyl esters as acyl donors

A kinetically controlled peptide synthesis catalyzed by α-chymotrypsin was performed in frozen aqueous solution (ice, -24 °C). The yield of the peptide was significantly improved by the use of the carbamoylmethyl (Cam) ester as the acyl donor instead of the conventional ethyl ester. The peptide yield increased up to ca. 90% when N-benzyloxycarbonyl (CBZ)-Phe-OCam and H-Phe-NH2 were used as the acyl donor and nucleophile, respectively. Such an improvement of the peptide yield in ice was also observed in the coupling of other CBZ-amino acid Cam esters as acyl donors. Furthermore, this approach was applied to the synthesis of peptides containing d-amino acids. The peptides such as CBZ-d-Phe-Phe-NH2, CBZ-Phe-d-Phe-NH2 and CBZ-d-Phe-d-Phe-NH2 were also obtained in excellent to moderate yields in ice. A high diastereoselectivity towards the l-l peptide was observed when the racemic amino acid Cam ester was used as the acyl donor in ice.

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.

A novel concept in combinatorial chemistry in solution with the advantages of solid-phase synthesis: Formation of N-betaines by multicomponent domino reactions

Advantages of solid-phase and liquid-phase synthesis are combined in a new concept of combinatorial chemistry: a domino sequence comprising Knoevenagel and hetero-Diels-Alder reactions, with subsequent hydrogenation starting from protected aminoaldehydes, 1.3-dicarbonyl compounds, and enol ethers leads to N-heterocycles of high diversity with a betaine structure, which are isolated in highly pure form by precipitation with diethyl ether (see scheme), Cbz = benzylocycarbonyl, Bn = benzyl.

New facile alkoxycarbonylating agent, alkyl pyrazole-1-carboxylates. The preparation and the utilities

Alkyl pyrazole-1-carboxylates (2), which were readily prepared from alkyl chloroformate or carbazate in good yields, were provided as the new facile alkoxycarbonylating agents toward the Grignard reagents for the synthesis of one carbon higher carboxylic esters. Also amines were alkoxycarbonylated by 2 to produce the corresponding urethanes even in an aqueous medium. Benzyl 3,5-dimethylpyrazole-1-carboxylate (2d) could be utilized for the Cbz-protection of amino acids and esters in good yield without any racemization.

New synthetic routes to α-amino acids and γ-oxygenated α-amino acids. Reductive denitration and oxidative transformations of γ-nitro-α-amino acids

Transformation of γ-nitro-α-amino acid derivatives into α-amino acids by reductive denitration, into the γ-oxo-α-amino acids by ozonolysis of the corresponding amino acid ester nitronate derivatives, and into γ-hydroxy-α-amino acid derivatives by subsequent reduction of the oxo functionality, can be achieved in good yields. As the γ-nitro-α-amino acid derivatives are prepared from N,O-protected dehydroalanines derivable from the corresponding alanine, serine and cysteine derivatives by specific routes, the overall procedures provide a means for selective conversion of these simple α-amino acids into more complex ones.