31872-98-7

Basic information

• Product Name: 5-Methyl-L-norleucine
• Synonyms: 5-methyl-L-norleucine;(S)-2-AMINO-5-METHYLHEXANOIC ACID;L-2-AMino-5-Methyl-hexanoic Acid;NSC 4073;H-L-HOLeu-OH·HCl (5-Methyl-L-norleucine);(S)-2-amino-5-methylhexanoicacid(new);H-HoLeu-OH;Methionine Impurity 3
• CAS NO: 31872-98-7
• Molecular Formula: C₇H₁₅NO₂
• Molecular Weight: 145.2
• EINECS: 250-848-2
• Product Categories: Amino Acids;Amino Acid Derivatives;Amino Acids & Derivatives;Chiral Reagents;unnatural amino acids
• Mol File: 31872-98-7.mol

Chemical Properties

• Melting Point: 254-256°C
• Boiling Point: 243.4 °C at 760 mmHg
• Flash Point: 101 °C
• Appearance: White solid
• Density: 1.014 g/cm³
• Vapor Pressure: 0.0106mmHg at 25°C
• Refractive Index: 1.463
• Storage Temp.: Refrigerator
• Solubility: Aqueous Acid (Slightly), Water (Slightly)
• PKA: 2.55±0.28(Predicted)
• CAS DataBase Reference: 5-Methyl-L-norleucine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Methyl-L-norleucine(31872-98-7)
• EPA Substance Registry System: 5-Methyl-L-norleucine(31872-98-7)

Safety Data

• Hazardous Substances Data: 31872-98-7(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Non-standard amino acid

InChI:InChI=1/C7H15NO2/c1-5(2)3-4-6(8)7(9)10/h5-6H,3-4,8H2,1-2H3,(H,9,10)

Upstream product

• 57224-44-9 2-amino-5-methylhexanoic acid hydrochloride 
• 73322-75-5 2-Amino-5-methyl-5-hexencarbonsaeure 
• 5440-33-5 2-acetamido-5-methylhexanoic acid 
• 75421-32-8 (Z)-2-benzamido-5-methyl-2-hexenoic acid 
• 75421-33-9 methyl (Z)-2-benzamido-5-methyl-2-hexenoate 
• 3558-32-5 DL-leucine 
• 56256-78-1 2-bromo-5-methyl-hexanoic acid 

Downstream Products

• 117560-22-2 (S)-2-Amino-5-methyl-hexanoic acid benzyl ester; compound with toluene-4-sulfonic acid 
• 2801-54-9 L-β-Methylleucin 

Relevant articles and documents

Resolution of non-protein amino acids via the microbial protease-catalyzed enantioselective hydrolysis of their N-unprotected esters

In the Aspergillus oryzae protease-catalyzed ester hydrolysis, substitution of N-unprotected amino acid esters for the corresponding N-protected amino acid esters resulted in a large enhancement of the hydrolysis rate, while the enantioselectivity was deteriorated strikingly when the substrates employed were the conventional methyl esters. This difficulty was overcome by employing esters bearing a longer alkyl chain such as the isobutyl ester. Utilizing this ester, amino acids carrying an aromatic side chain were resolved with excellent enantioselectivities (E=50 to >200). With amino acids bearing an aliphatic side chain also, good results in terms of the hydrolysis rate and enantioselectivity were obtained by employing such an ester as the isobutyl ester. Moreover, the enantioselectivity proved to be enhanced further by conducting the reaction at low temperature. This procedure was applicable to the case where the enantioselectivity was not high enough even by the use of the isobutyl ester.

Resolution of non-protein amino acids via microbial protease-catalyzed ester hydrolysis: Marked enhancement of enantioselectivity by the use of esters with longer alkyl chains and at low temperature

In the microbial protease-catalyzed hydrolysis of amino acid esters with the free α-amino group, the enantioselectivity can be enhanced greatly by employing esters with longer alkyl chains such as the isobutyl ester instead of the conventional methyl ester and by conducting the reaction at low temperature.

Studies on Angiotensin Converting Enzyme Inhibitors. 4. Synthesis and Angiotensin Converting Enzyme Inhibitory Activities of 3-Acyl-1-alkyl-2-oxoimidazolidine-4-carboxylic Acid Derivatives

(4S)-1-Alkyl-3-acyl>-2-oxoimidazolidine-4-carboxylic acid derivatives (3) were prepared by two methods.Their angiotensin converting enzyme (ACE) inhibitory activities and antihypertensive effects were evaluated, and the structure-activity relationships were discussed.The dicarboxylic acids 3a-n possessing S,S,S configuration showed potent in vitro ACE inhibitory activities with IC 50 values of 1.1x10-8-1.5x10-9 M.The most potent compound in this series, monoester 3p, had an ID 50 value of 0.24 mg/kg, po for inhibition of angiotensin I induced pressor response in normotensive rats and produced a dose-dependent decrease in systolic blood pressure of spontaneously hypertensive rats (SHRs) at doses of 1-10 mg/kg, po.

1,2-Bis(diphenylphosphino)-1-cyclohexylethane. A New Chiral Phosphine Ligand for Catalytic Chiral Hydrogenations

The new chiral bidentate phosphine ligand (R)-1,2-bis(diphenylphosphino)-1-cyclohexylethane ((R)-Cycphos) has been prepared.The rhodium(I) cationic complex of this phosphine serves as an effective homogeneous asymmetric hydrogenation catalyst for the reduction of (Z)-α-amidoacrylic acids at ambient temperature and pressure.Optical yields for the corresponding (S)-α-amino acid derivatives that are produced are generally above 90percent.The success of this ligand in giving higher optical yields than those obtained from other structurally analogous phosphines is rationalized in terms of the bulky cyclohexyl substituent affording a more stereochemically rigid chelating phosphine.