61-90-5 Usage
description
L-leucine is one of the eight essential amino acids, and belonging to the aliphatic amino acids within twenty kinds of proteins. L-leucine and L-isoleucine and L-valine are called three branched chain amino acids. L-leucineLeucine and D-leucine are enantiomers . It is a white shiny hexahedral crystal or white crystalline powder at room temperature , Odorless, slightly bitter . In the presence of hydrocarbons ,it is stable in the aqueous mineral acid. Per gram is dissolved in 40ml water and about 100ml acetic acid. Very slightly soluble in ethanol or ether, dissolved in formic acid, dilute hydrochloric acid, a solution of alkali hydroxides and a solution of carbonates.
L-leucine can promote insulin secretion, can lower blood sugar; promote sleep, reduce sensitivity to pain, migraine headaches, anxiety and ease tension, reduce symptoms of chemical reactions disorder in the body caused by alcohol , and helps control alcoholism; it has a role in the treatment of dizziness , also can promote skin wound and bone healing, so doctors usually advise patients to take leucine supplements after surgery. amino acid infusion and comprehensive amino acid preparations are often formulated to be used in the treatment or health care; also be used as food, cosmetics and feed additives and plant growth promoter.
The best food sources of leucine include brown rice, beans, meat, nuts, soy flour, and whole wheat. Excessive intake can also cause side effects, high intake can cause pellagra, vitamin A deficiency, dermatitis, diarrhea, mental disorders and other issues,which needs to be paid attention to . Diet containing too much leucine will increase the number of ammonia in the body and destroy the liver and kidney function. Therefore, patients with impaired liver or kidney function should not be excessive intake, otherwise it will exacerbate the condition.
Chemical Properties
Different sources of media describe the Chemical Properties of 61-90-5 differently. You can refer to the following data:
1. White shiny hexahedral crystals or white crystalline powder. Slightly bitter (DL-leucine is sweet). Sublimation at 145~148 ℃. Melting point 293~295 ℃ (decomposition). It belongs to the essential amino acids,and adult men requirement is 2.2g/d (151 version). It is necessary in normal growth for infants and maintaining normal nitrogen balance for adults.
Natural products are found in the spleen, heart, etc., and are present in a variety of plant and animal tissues in the form of the proteins, free out after decomposition and corruption.
2. L-Leucine is odorless and has a slightly bitter taste. L-Leucine is a branched-chain, essential amino acid that stimulates
muscle protein synthesis.
3. White crystalline powder
4. Leucine occurs as a white or almost off-white crystalline powder or
shiny flakes.
Uses
Different sources of media describe the Uses of 61-90-5 differently. You can refer to the following data:
1. Amino acid drugs. Used as amino acid infusion and comprehensive amino acid preparations. For the diagnosis and treatment of children with idiopathic high blood sugar and glucose metabolism disorders,bile liver disease associated with reduced secretion , anemia, poisoning, muscular dystrophy, poliomyelitis, neuritis and mental illness. Diabetes, cerebral vascular sclerosis and kidney disease associated with proteinuria and hematuria is contraindicated. Gastric and duodenal ulcer patients should not be served.
The product is used as a nutritional supplement,an amino acid infusion preparation and a comprehensive amino acid preparation,a hypoglycemic agent, a plant growth promoter.The product can be used as a spice according to GB 2760-8 .
2. L-Leucine plays a vital role in hemoglobin formation, protein synthesis and metabolic functions. It assists the growth and repair of muscle and bone tissue. It is used in the treatment of amyotrophic lateral sclerosis - Lou Gehrig's disease. It prevents the breakdown of muscle proteins after trauma or severe stress and may be beneficial for individuals with phenylketonuria. It is also used as a food additive and flavor enhancer. Further, it is used to preserve muscle glycogen.
3. L-Leucine is an essential amino acid. It is also considered to be a branched chain amino acid, along with L-Isoleucine and L-Valine. It is used as a cell culture media component in the commercial biomanufacture of therapeutic recombinant proteins and monoclonal antibodies.
4. L-Leucine is an essential amino acid. L-Leucine acts as a nutrient signal to stimulate protein synthesis. It has also activates the mammalian target of rapamycin kinase that regulates cell growth.
toxicity
Safe for food (FDA, §172.3202000).
LD505379mg/kg (rat, subcutaneously).
Description
Small, white, lustrous plates, or a white, crystalline powder, with
a slightly bitter taste. One g dissolves in about 40 mL of water
and in about 100 mL of acetic acid. It is sparingly soluble in
alcohol, but is soluble in dilute hydrochloric acid and in solutions
of alkali hydroxides and carbonates. ι-Leucine may be synthesized by bromination, followed by amination of isocaproic acid; via the
acetamidomalonic ester; by isolation from gluten, casein, keratin;
from hydantoin.
Occurrence
Reported found as a constituent in proteins; also present in the free state in the human body
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.
Definition
ChEBI: The L-enantiomer of leucine.
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
Recreating the natural evolutionary trend in key microdomains provides an effective strategy for engineering of a thermomicrobial N-demethylase
Gu, Zhenghua,Guo, Zitao,Shao, Jun,Shen, Chen,Shi, Yi,Tang, Mengwei,Xin, Yu,Zhang, Liang
, (2022/03/09)
N-demethylases have been reported to remove the methyl groups on primary or secondary amines, which could further affect the properties and functions of biomacromolecules or chemical compounds; however, the substrate scope and the robustness of N-demethylases have not been systematically investigated. Here we report the recreation of natural evolution in key microdomains of the Thermomicrobium roseum sarcosine oxidase (TrSOX), an N-demethylase with marked stability (melting temperature over 100 C) and enantioselectivity, for enhanced substrate scope and catalytic efficiency on -C-N-bonds. We obtained the structure of TrSOX by crystallization and X-ray diffraction (XRD) for the initial framework. The natural evolution in the nonconserved residues of key microdomains—including the catalytic loop, coenzyme pocket, substrate pocket, and entrance site—was then identified using ancestral sequence reconstruction (ASR), and the substitutions that accrued during natural evolution were recreated by site-directed mutagenesis. The single and double substitution variants catalyzed the N-demethylation of N-methyl-L-amino acids up to 1800- and 6000-fold faster than the wild type, respectively. Additionally, these single substitution variants catalyzed the terminal N-demethylation of non-amino-acid compounds and the oxidation of the main chain -C-N- bond to a -C=N- bond in the nitrogen-containing heterocycle. Notably, these variants retained the enantioselectivity and stability of the initial framework. We conclude that the variants of TrSOX are of great potential use in N-methyl enantiomer resolution, main-chain Schiff base synthesis, and alkaloid modification or degradation.
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).
