Leucine

Base Information

• Chemical Name: Leucine
• CAS No.: 21675-61-6
• Deprecated CAS: 7005-03-0
• Molecular Formula: C6H13NO2
• Molecular Weight: 131.17
• European Community (EC) Number: 200-522-0
• NSC Number: 760100
• UNII: GMW67QNF9C
• DSSTox Substance ID: DTXSID9023203
• Nikkaji Number: J1.167C
• Wikipedia: Leucine
• Wikidata: Q483745
• NCI Thesaurus Code: C29599
• RXCUI: 6308
• Metabolomics Workbench ID: 42493
• ChEMBL ID: CHEMBL291962
• Mol file: 21675-61-6.mol

Synonyms:L-Isomer Leucine;L-Leucine;Leucine;Leucine, L Isomer;Leucine, L-Isomer

Chemical Property of Leucine

Chemical Property:

• Melting Point: 293oC
• Boiling Point: 225.772 °C at 760 mmHg
• Flash Point: 90.344 °C
• PSA: 63.32000
• Density: 1.036 g/cm³
• LogP: 1.14470
• Storage Temp.: 2-8°C
• XLogP3: -1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 131.094628657
• Heavy Atom Count: 9
• Complexity: 101

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s): R
• Hazard Codes: R
• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Amino Acids and Derivatives
• Canonical SMILES: CC(C)CC(C(=O)O)N
• Isomeric SMILES: CC(C)C[C@@H](C(=O)O)N
• Recent ClinicalTrials: Rapid Antidepressant Effects of Leucine
• Recent EU Clinical Trials: A Phase 2, Multicenter, Randomized, Double-Blind, Placebo-Controlled Trial to Evaluate the Efficacy and Safety of AXA1665 in Subjects With Liver Cirrhosis and Prior Overt Hepatic Encephalopathy (EMMPOWER)
• Recent NIPH Clinical Trials: Phase III trial to evaluate the efficacy of nutrition and exercise intervention on lean body mass loss after gastrectomy for gastric cancer (NEx-RCT)-Open-label randomized trial

Technology Process of Leucine

There total 655 articles about Leucine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

L-leucine-p-nitroanilide (16010-99-4,110893-28-2,86237-92-5,63324-49-2,6664-98-8) → 4-nitro-aniline (100-01-6,104810-17-5) + LEUCINE (328-39-2,21675-61-6,25248-98-0,70-45-1)

Guidance literature:

With Rhodococcus erythropolis TA₃₇ acylamidase; at 37 ℃; for 0.333333h; pH=7.5; Kinetics; aq. buffer; Enzymatic reaction;

DOI:10.1134/S0006297910080080

Reference yield:

pholipeptin → D-Serine (312-84-5,83245-15-2) + L-threonine (72-19-5,134357-96-3,7013-32-3,82822-12-6) + (R)-leucine (328-38-1,21675-61-6,25248-98-0,70-45-1) + L-isoleucine (73-32-5,959215-79-3,18875-42-8) + (2R)-aspartic acid (1783-96-6,25608-40-6,27881-03-4,32505-46-7,52526-39-3) + L-Aspartic acid (56-84-8,25608-40-6,27881-03-4,32505-46-7,52526-39-3)

Guidance literature:

With hydrogenchloride; at 120 ℃; for 20h; Product distribution;

DOI:10.1021/jo9603993

Reference yield:

(S)-2-amino-4-methyl-N-(4-nitrophenyl)valeramide (4178-93-2,110893-28-2,86237-92-5,63324-49-2,6664-98-8) → L-leucine (61-90-5,21675-61-6,25248-98-0,70-45-1) + 4-nitro-aniline (100-01-6,104810-17-5)

Guidance literature:

With water; leucine aminopeptidase; at 25 ℃; under 750.06 Torr; Rate constant; Thermodynamic data; influence of Zn⁽²⁺⁾, influence of pH, Mg⁽²⁺⁾ modified enzyme, different pressures, activation volume;

DOI:10.1246/bcsj.58.1349

upstream raw materials:

(RS)-leucinonitrile

L-leucine

ethyl 2-acetyl-4-methylpentanoate

2-isobutyl-malonamic acid

Downstream raw materials:

N-(N-benzoyl-glycyl)-leucine

DL-leucine methyl ester

Ac-ΔPhe-(S)-Leu-OH

DL-leucine ethyl ester

Refernces

• 1、 Goto, Yoshikuni,Yoshioka, Rina,Arisaka, Naomi,Hattori, Akira,Tsujimoto, Masafumi. "Involvement of glutamine-238 in the substrate specificity of human laeverin/aminopeptidase Q". . p. 24 - 27. Retrieved 2011.
• 2、 Shimojima, Yukiji,Hayashi, Hiroshi,Ooka, Tadaaki,Shibukawa, Mitsuru,Iitaka, Yoichi. "(STUDIES ON AI-77s, MICROBIAL PRODUCTS WITH PHARMACOLOGICAL ACTIVITY) STRUCTURES AND THE CHEMICAL NATURE OF AI-77s". . p. 5435 - 5438. Retrieved 1982.
• 3、 Meierhenrich, Uwe J.,Filippi, Jean-Jacques,Meinert, Cornelia,Hoffmann, Soren V.,Bredehoeft, Jan Hendrik,Nahon, Laurent. "Photolysis of rac-leucine with circularly polarized synchrotron radiation". . p. 1651 - 1659. Retrieved 2010.
• 4、 Zhuravleva,Afiyatullov,Ermakova,Nedashkovskaya,Dmitrenok,Denisenko,Kuznetsova. "New C14-surfactin methyl ester from the marine bacterium Bacillus pumilus KMM 456". . p. 2137 - 2142. Retrieved 2010.
• 5、 Lee, Seoung Rak,Lee, Dahae,Yu, Jae Sik,Benndorf, René,Lee, Sullim,Lee, Dong-Soo,Huh, Jungmoo,Wilhelm de Beer,Kim, Yong Ho,Beemelmanns, Christine,Kang, Ki Sung,Kim, Ki Hyun. "Natalenamides A–C, cyclic tripeptides from the termite-associated Actinomadura sp. RB99". . . Retrieved 2018.
• 6、 Tong, Ling,Zhu, Zhi,Pi, Hui-Fang,Ruan, Han-Li,Wu, Ji-Zhou,Zhang, Peng. "A New Cyclic Peptide from Bulbs of Fritillaria hupehensis". . p. 923 - 925. Retrieved 2015.
• 7、 Tareq, Fakir Shahidullah,Shin, Hee Jae. "Bacilotetrins A and B, Anti-Staphylococcal Cyclic-Lipotetrapeptides from a Marine-Derived Bacillus subtilis". . p. 2889 - 2892. Retrieved 2017.
• 8、 Freer, Isabel,Pedrocchi-Fantoni, Giuseppe,Picken, Douglas J.,Overton, Karl H.. "Stereochemistry of the Leucine 2,3-Aminomutase from Tissue Cultures of Andrographis paniculata". . p. 80 - 82. Retrieved 1981.
• 9、 Rubinstein, Irina,Clodic, Gilles,Bolbach, Gerard,Weissbuch, Isabelle,Lahav, Meir. "Racemic β-sheets as templates for the generation of homochiral (isotactic) peptides from aqueous solutions of (RS)-valine or -leucine N-carboxy-anhydrides: relevance to biochirogenesis". . p. 10999 - 11009. Retrieved 2008.
• 10、 Chen, Min,Chen, Rouwen,Ding, Wenping,Li, Yanqun,Tian, Xinpeng,Yin, Hao,Zhang, Si. "Structures and antitumor activities of ten new and twenty known surfactins from the deep-sea bacterium Limimaricola sp. SCSIO 53532". . . Retrieved 2022/01/11.