61-90-5 Usage
Description
L-Leucine is one of the eight essential amino acids, belonging to the aliphatic amino acids within the twenty types of proteins. It is a white, crystalline powder or small, white, lustrous plates with a slightly bitter taste. L-Leucine is stable in the presence of hydrocarbons and aqueous mineral acid. It is soluble in water, acetic acid, dilute hydrochloric acid, and solutions of alkali hydroxides and carbonates. L-Leucine is an essential nutrient for normal growth, maintenance of nitrogen balance in adults, and plays a vital role in hemoglobin formation, protein synthesis, and metabolic functions.
Uses
1. Used in Amino Acid Drugs:
L-Leucine is used as an amino acid infusion and comprehensive amino acid preparation for the diagnosis and treatment of various conditions such as idiopathic high blood sugar, glucose metabolism disorders, bile liver disease, anemia, poisoning, muscular dystrophy, poliomyelitis, neuritis, and mental illness. However, it is contraindicated for diabetes, cerebral vascular sclerosis, kidney disease associated with proteinuria and hematuria, and gastric and duodenal ulcer patients.
2. Used as a Nutritional Supplement:
L-Leucine serves as a nutritional supplement, promoting insulin secretion, lowering blood sugar, and aiding in sleep, pain reduction, and anxiety relief. It also helps in the treatment of dizziness and promotes skin wound and bone healing, making it a common recommendation for post-surgery patients.
3. Used as a Food Additive and Flavor Enhancer:
L-Leucine is used in the food industry as an additive and flavor enhancer, as well as a plant growth promoter.
4. Used in Cell Culture Media:
In the commercial biomanufacture of therapeutic recombinant proteins and monoclonal antibodies, L-Leucine is used as a component of cell culture media.
5. Used in the Treatment of Amyotrophic Lateral Sclerosis (ALS) Lou Gehrig's Disease:
L-Leucine helps prevent the breakdown of muscle proteins after trauma or severe stress and may be beneficial for individuals with phenylketonuria.
6. Used in the Preservation of Muscle Glycogen:
L-Leucine plays a role in preserving muscle glycogen, which is essential for muscle function and energy.
7. Used in the Regulation of Cell Growth:
L-Leucine acts as a nutrient signal to stimulate protein synthesis and activates the mammalian target of rapamycin kinase, which regulates cell growth.
Occurrence:
L-Leucine is found as a constituent in proteins and is also present in the free state in the human body. Natural sources include brown rice, beans, meat, nuts, soy flour, and whole wheat.
Chemical Properties:
L-Leucine is odorless, with a slightly bitter taste, and occurs as a white or almost off-white crystalline powder or shiny flakes. It sublimates at 145-148°C and has a melting point of 293-295°C (decomposition). L-Leucine is a branched-chain, essential amino acid that stimulates muscle protein synthesis.
Precautions:
Excessive intake of L-Leucine can cause side effects such as pellagra, vitamin A deficiency, dermatitis, diarrhea, and mental disorders. High intake can also increase the number of ammonia in the body, potentially damaging liver and kidney function. Therefore, patients with impaired liver or kidney function should avoid excessive intake of L-Leucine.
toxicity
Safe for food (FDA, §172.3202000).
LD505379mg/kg (rat, subcutaneously).
Production Methods
Leucine is produced microbially by incubating an amino-acidproducing
microorganism including but not exclusive to Pseudomonas,
Escherichia, Bacillus, or Staphylococcus in the presence of
oxygen and a hydrocarbon. The nutrient medium should contain an
inhibitory amount of a growth inhibitor that is a chemically similar
derivative of leucine (e.g. methylallylglycine, a-hydrozinoisocaproic
acid, or b-cyclopentanealanine) to inhibit the growth of the
organism except for at least one mutant that is resistant to the
inhibitory effect. The resistant mutant is then isolated and grown in
the presence of oxygen and the hydrocarbon in the absence of the
inhibitor. The mutant cells are then harvested and a nutrient
medium is formed that includes a hydrocarbon as the sole source of
carbon. Finally, the harvested cells are incubated in the medium in
the presence of oxygen.
Preparation
By bromination followed by amination of isocaproic acid; via the acetamidomalonic ester; by isolation from gluten,
casein, keratin; from hydantoin.
Pharmaceutical Applications
Leucine is used in pharmaceutical formulations as a flavoring
agent. It has been used experimentally as an antiadherent to
improve the deagglomeration of disodium cromoglycate micro-particles and other compounds in inhalation preparations; and as
a tablet lubricant. Leucine copolymers have been shown to
successfully produce stable drug nanocrystals in water.
Biochem/physiol Actions
Leucine is a non-glucogenic, essential amino acid. It is a branched-chain amino acid that is a structural component of proteins. Leucine positively influences insulin release to eliminate toxic sugars out of the blood. The degradation of leucine leads to the formation of ketone bodies.
Safety
Leucine is an essential amino acid and is consumed as part of a
normal diet. It is generally regarded as a nontoxic and nonirritant
material. It is moderately toxic by the subcutaneous route.
LD50 (rat, IP): 5.379 g/kg
storage
Leucine is sensitive to light and moisture, and should be stored in an
airtight container in a cool, dark, dry place.
Purification Methods
Likely impurities are isoleucine, valine, and methionine. Crystallise L-leucine from water by adding 4 volumes of EtOH. It sublimes at 180-188o/0.3mm with 99.1% recovery, and unracemised [Gross & Gradsky J Am Chem Soc 77 1678 1955]. [Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 p 2075-2094 1961, Kameda et al. J Pharm Soc Jpn 78 763 1958, Beilstein 4 IV 2738.]
Incompatibilities
Leucine is incompatible with strong oxidizing agents.
Regulatory Status
Included in the FDA Inactive Ingredients Database (IV infusion; oral
tablets). Included in nonparenteral medicines licensed in the UK.
Check Digit Verification of cas no
The CAS Registry Mumber 61-90-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 1 respectively; the second part has 2 digits, 9 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 61-90:
(4*6)+(3*1)+(2*9)+(1*0)=45
45 % 10 = 5
So 61-90-5 is a valid CAS Registry Number.
InChI:InChI=1/C6H13NO2/c1-4(2)3-5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t5-/m0/s1
61-90-5Relevant articles and documents
Structures and antitumor activities of ten new and twenty known surfactins from the deep-sea bacterium Limimaricola sp. SCSIO 53532
Chen, Min,Chen, Rouwen,Ding, Wenping,Li, Yanqun,Tian, Xinpeng,Yin, Hao,Zhang, Si
, (2022/01/11)
Surfactins are natural biosurfactants with myriad potential applications in the areas of healthcare and environment. However, surfactins were almost exclusively produced by the bacterium Bacillus species in previous reported literatures, together with difficulty in isolating pure monomer, which resulted in making extensive effort to remove duplication and little discovery of new surfactins in recent years. In the present study, the result of Molecular Networking indicated that Limimaricola sp. SCSIO 53532 might well be a potential resource for surfacin-like compounds based on OSMAC strategy. To search for new surfactins with significant biological activity, further study was undertaken on the strain. As a result, ten new surfactins (1–10), along with twenty known surfactins (11–30), were isolated from the ethyl acetate extract of SCSIO 53532. Their chemical structures were established by detailed 1D and 2D NMR spectroscopy, HRESIMS data, secondary ion mass spectrometry (MS/MS) analysis, and chemical degradation (Marfey's method) analysis. Cytotoxic activities of twenty-seven compounds against five human tumor cell lines were tested, and five compounds showed significant antitumor activities with IC50 values less than 10 μM. Furtherly, analysis of structure–activity relationships revealed that the branch of side chain, the esterification of Glu or Asp residue, and the amino acid residue of position 7 possessed a great influence on antitumor activity.
Direct monitoring of biocatalytic deacetylation of amino acid substrates by1H NMR reveals fine details of substrate specificity
De Cesare, Silvia,McKenna, Catherine A.,Mulholland, Nicholas,Murray, Lorna,Bella, Juraj,Campopiano, Dominic J.
supporting information, p. 4904 - 4909 (2021/06/16)
Amino acids are key synthetic building blocks that can be prepared in an enantiopure form by biocatalytic methods. We show that thel-selective ornithine deacetylase ArgE catalyses hydrolysis of a wide-range ofN-acyl-amino acid substrates. This activity was revealed by1H NMR spectroscopy that monitored the appearance of the well resolved signal of the acetate product. Furthermore, the assay was used to probe the subtle structural selectivity of the biocatalyst using a substrate that could adopt different rotameric conformations.
Isolation, Structure Determination, and Total Synthesis of Hoshinoamide C, an Antiparasitic Lipopeptide from the Marine Cyanobacterium Caldora penicillata
Iwasaki, Arihiro,Ohtomo, Keisuke,Kurisawa, Naoaki,Shiota, Ikuma,Rahmawati, Yulia,Jeelani, Ghulam,Nozaki, Tomoyoshi,Suenaga, Kiyotake
, p. 126 - 135 (2021/01/13)
Hoshinoamide C (1), an antiparasitic lipopeptide, was isolated from the marine cyanobacterium Caldora penicillata. Its planar structure was elucidated by spectral analyses, mainly 2D NMR, and the absolute configurations of the α-amino acid moieties were determined by degradation reactions followed by chiral-phase HPLC analyses. To clarify the absolute configuration of an unusual amino acid moiety, we synthesized two possible diastereomers of hoshinoamide C and determined its absolute configuration based on a comparison of their spectroscopic data with those of the natural compound. Hoshinoamide C (1) did not exhibit any cytotoxicity against HeLa or HL60 cells at 10 μM, but inhibited the growth of the parasites responsible for malaria (IC50 0.96 μM) and African sleeping sickness (IC50 2.9 μM).