210345-86-1

Basic information

• Product Name: (R)-2-(aMinoMethyl)-3-Methylbutanoic acid
• Synonyms: (R)-2-(aMinoMethyl)-3-Methylbutanoic acid;Butanoic acid, 2-(aminomethyl)-3-methyl-, (2R)-;EOS-62015
• CAS NO: 210345-86-1
• Molecular Formula: C6H13NO2
• Molecular Weight: 131.17292
• Mol File: 210345-86-1.mol

Chemical Properties

• Melting Point: 238-239 °C
• Boiling Point: 232.0±23.0 °C(Predicted)
• Appearance: /
• Density: 1.035±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 3.50±0.11(Predicted)
• CAS DataBase Reference: (R)-2-(aMinoMethyl)-3-Methylbutanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-(aMinoMethyl)-3-Methylbutanoic acid(210345-86-1)
• EPA Substance Registry System: (R)-2-(aMinoMethyl)-3-Methylbutanoic acid(210345-86-1)

Safety Data

• Hazardous Substances Data: 210345-86-1(Hazardous Substances Data)

Usage

Uses

Used in Nutritional Supplements:
Leucine is used as a nutritional supplement for athletes and bodybuilders to enhance their workouts and promote muscle recovery. Its branched-chain structure allows for efficient absorption and utilization by the body, contributing to increased muscle protein synthesis and reduced muscle breakdown.
Used in Muscle Growth Promotion:
Leucine is used as a muscle growth promoter due to its ability to stimulate the mTOR signaling pathway, which is essential for muscle protein synthesis. By increasing the availability of leucine in the body, it can help promote muscle growth and reduce muscle wasting in various conditions, such as aging, injury, or disease.
Used in Weight Loss Support:
Leucine is used to support weight loss efforts by increasing the body's metabolic rate and promoting the oxidation of fat. Its role in protein synthesis also helps maintain lean muscle mass during weight loss, which is crucial for preserving basal metabolic rate and preventing muscle loss.
Used in Exercise Performance Improvement:
Leucine is used to improve exercise performance by providing an additional source of energy during intense physical activity. Its role in muscle repair and protein synthesis also helps reduce muscle fatigue and soreness, allowing for better recovery and performance in subsequent workouts.
Used in High-Protein Foods:
Leucine is naturally found in high-protein foods such as meat, dairy products, and legumes. Consuming these foods as part of a balanced diet can help ensure adequate leucine intake, supporting overall health and well-being.
Used in Pharmaceutical Applications:
Leucine is used in the pharmaceutical industry for the development of medications targeting various health conditions, such as muscle wasting, cachexia, and other muscle-related disorders. Its role in protein synthesis and muscle repair makes it a valuable component in the formulation of therapeutic agents.

Upstream product

• 191664-12-7 N-[(R)-2-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-3-methyl-butyl]-benzamide 
• 501331-00-6 (4R)-isopropyl-2-((S)-1-phenylethyl)-isoxazolidin-5-one 
• 134806-92-1 2-isopropyl-acrylic acid benzyl ester 
• 501330-87-6 2-isopropyl-3-oxo-butyric acid benzyl ester 
• 501331-05-1 (R)-3-Methyl-2-[((S)-1-phenyl-ethylamino)-methyl]-butyric acid tert-butyl ester 
• 145589-03-3 (R)-4-benzyl-3-(3-methylbutyryl)oxazolidin-2-one 
• 72604-80-9 (R)-2-(hydroxymethyl)-3-methylbutanoic acid 
• 145589-03-3 (S)-4-benzyl-3-(3-methylbutanoyl)oxazolidin-2-one 
• 1138323-75-7 (2R)-([{(benzyloxy)carbonyl}amino]methyl)-3-methylbutanoic acid 
• 1415986-74-1 (4S)-4-benzyl-3-[(2R)-2-(dibenzylamino)methyl-3-methylbutanoyl]-1,3-oxazolidin-2-one 
• 1415986-80-9 (2R)-2-(dibenzylamino)methyl-3-methylbutanoic acid 
• 1415986-77-4 S-ethyl (2R)-2-(dibenzylamino)methyl-3-methylbutanethioate 
• 470454-06-9 4-(R)-benzyl-3-(2-(R)-benzyloxymethyl-3-methylbutyryl)oxazolidin-2-one 
• 218285-59-7 (R)-N-Benzyloxy-2-hydroxymethyl-3-methyl-butyramide 

Downstream Products

• 191664-14-9 (R)-2-(((tert-butoxycarbonyl)amino)methyl)-3-methylbutanoic acid 
• 501331-02-8 (2R)-2-({[(9H-fluoren-9-ylmethoxy)carbonyl]amino}methyl)-3-methylbutanoic acid 
• 191664-18-3 (R)-2-({(R)-3-[(R)-2-(tert-Butoxycarbonylamino-methyl)-3-methyl-butyrylamino]-2-methyl-propionylamino}-methyl)-4-methyl-pentanoic acid benzyl ester 
• 191664-19-4 C₄₆H₇₈N₆O₉ 
• 210345-68-9 (R)-2-[((R)-3-{(R)-2-[((2R,3R)-3-tert-Butoxycarbonylamino-2-methyl-butyrylamino)-methyl]-3-methyl-butyrylamino}-2-methyl-propionylamino)-methyl]-4-methyl-pentanoic acid benzyl ester 
• 210345-69-0 Boc-(R)-β²-HVal-(R)-β²-HAla-(R)-β²-HLeu-(2R,3R)-β^2,3-HAla(α-Me)-(R)-β²-HVal-(R)-β²-HAla-(R)-β²-HLeu-OBn 

Relevant articles and documents

Synthesis and biological evaluation of gramicidin S-inspired cyclic mixed α/β-peptides

Via a Mannich reaction involving a dibenzyliminium species and the titanium enolates of Evans' chiral acylated oxazolidinones the β2-amino acids (R)- and (S)-Fmoc-β2homovaline and (R)-Fmoc- β2homoleucine are synthesized. T

Enantioselective synthesis of beta-amino acids using hexahydrobenzoxazolidinones as chiral auxiliaries

A practical synthetic route for the asymmetric synthesis of β2-amino acids is described. In the first step, the procedure involves the N-acylation of readily available, enantiopure hexahydrobenzoxazolidinone (4R,5R)-1 with 3-methylbutanoyl chloride 2, 4-methylpentanoic acid 3, and 3-(1-tert-butoxycarbonyl)-1H-indol-3-yl)propanoic acid 4 to afford derivatives 5a, 5b, and 5c, respectively, which were alkylated with high diastereoselectivity by means of reaction between their sodium enolates and benzyl bromoacetate. Removal of the chiral auxiliary from the alkylated products followed by hydrogenation and hydrolysis gave β2-amino acids (S)-10a, (S)-10b, and (S)-10c, which were N-protected with Fmoc. Enantiomeric (R)-10a-c were similarly prepared from the isomeric hexahydrobenzoxazolidinone (4S,5S)-1; thus, the route presented here provides access to both enantiomers of valuable highly enantioenriched β2-amino acids.

Asymmetric synthesis of β2-amino acids: 2-substituted-3-aminopropanoic acids from N-acryloyl SuperQuat derivatives

Conjugate addition of lithium dibenzylamide to (S)-N(3)-acryloyl-4- isopropyl-5,5-dimethyloxazolidin-2-one (derived from l-valine) and alkylation of the resultant lithium β-amino enolate provides, after deprotection, a range of (S)-2-alkyl-3-aminopropanoic acids in good yield and high ee. Alternatively, via a complementary pathway, conjugate addition of a range of secondary lithium amides to (S)-N(3)-(2′-alkylacryloyl)-4-isopropyl-5,5- dimethyloxazolidin-2-ones, diastereoselective protonation with 2-pyridone, and subsequent deprotection furnishes a range of (R)-2-alkyl- and (R)-2-aryl-3-aminopropanoic acids in good yield and high ee. Additionally, the boron-mediated aldol reaction of β-amino N-acyl oxazolidinones is a highly diastereoselective method for the synthesis of a range of β-amino- β′-hydroxy N-acyl oxazolidinones. The Royal Society of Chemistry.

Efficient synthesis of enantiomerically pure β2-amino acids via chiral isoxazolidinones

We report a practical and scalable synthetic route for the preparation of α-substituted β-amino acids (β2-amino acids). Michael addition of a chiral hydroxylamine, derived from α-methylbenzylamine, to an α-alkylacrylate followed by cyclization gives a diastereomeric mixture of α-substituted isoxazolidinones. These diastereomers are separable by column chromatography. Subsequent hydrogenation of the purified isoxazolidinones followed by Fmoc protection affords enantiomerically pure Fmoc-β2-amino acids, which are useful for β-peptide synthesis. This route provides access to both enantiomers of a protected β2-amino acid.

A practical method for the conversion of β-hydroxy carboxylic acids into the corresponding β-amino acids

Optically active α- or β-substituted βamino acids were synthesized from the corresponding β-hydroxy acids in 4 steps in excellent yield. Stereochemistry was retained at the α-position and reversed at the β-position during the conversion.

β2- And β3-Peptides with Proteinaceous Side Chains: Synthesis and Solution Structures of Constitutional Isomers, a Novel Helical Secondary Structure and the Influence of Solvation and Hydrophobic Interactions on Folding

Enantiomerically pure β-amino-acid derivatives with the side chains of Ala, Val, and Leu in the 2- or 3-position (β2- and β3-amino acids, resp.), as well as with substituents in both the 2- and 3-positions (β2,3-amino acids, of like-configuration) have been prepared (compounds 8-17) and incorporated (by stepwise synthesis and fragment coupling, intermediates 24-34) into β-hexa-, β-hepta-, and β-dodecapeptides (1-17). The new and some of the previously prepared β-peptides (35-39) showed NH/ND exchange rates (in MeOH at room temperature) with τ1/2 values of up to 60 days, unrivalled by short chain α-peptides. All β-peptides 1-7 were designed to be able to attain the previously described 31-helical structure (Figs. 1 and 2). CD Measurements (Fig. 4), indicating a new secondary structure of certain β-peptides constructed of β2- and β3-amino acids, were confirmed by detailed NMR solution-structure analyses: a β2-heptapeptide (2c) and a β2,3-hexapeptide (7c) have the 31-helical structure (Figs. 6 and 7), while to a β2/β3-hexapeptide (4) with alternating substitution pattern H-(β2-Xaa-β3-Xaa)3-OH a novel, unusual helical structure (in (D5)pyridine, Fig. 8; and in CD3OH, Figs. 9 and 10) was assigned, with a central ten-membered and two terminal twelve-membered H-bonded rings, and with C=O and N-H bonds pointing alternatively up and down along the axis of the helix (Fig. 11). Thus, for the first time, two types of β-peptide turns have been identified in solution. Hydrophobic interactions of and hindrance to solvent accessibility by the aliphatic side chains are discussed as possible factors influencing the relative stability of the two types of helices.

Synthesis of a β-hexapeptide from (R)-2-aminomethyl-alkanoic acids and structural investigations

The (R) α-branched β-amino acid derivatives 3-5 with the side chains of alanine, valine and leucine are prepared by amino-methylation of acyloxazolidinones 2a-c and are used for the synthesis of the trifluoroacetate salt 9 of H(-β2-HVal-β2-HAla-β2-HLeu) 2-OH. The CD spectrum of compound 9 is compared with that of the isomer H(-β3-HVal-β3-HAla-β3-HLeu) 2-OH (1) built from the corresponding β-branched β-amino acids.