3060-46-6

Basic information

• Product Name: N-Methyl-L-leucine
• Synonyms: H-ALPHA-ME-LEU-OH;H-(ME)LEU-OH;ALPHA-METHYL-L-LEUCINE;N-METHYL-L-LEUCINE;N-ME-LEU-OH;N-ME-LEUCINE;N-ALPHA-METHYL-L-LEUCINE;L-N-Methylleucine
• CAS NO: 3060-46-6
• Molecular Formula: C₇H₁₅NO₂
• Molecular Weight: 145.2
• Product Categories: Amino Acid Derivatives;amino acid;amino acids;Pyrazoles,Pyrazines
• Mol File: 3060-46-6.mol

Chemical Properties

• Melting Point: 300 °C
• Boiling Point: 226.1 °C at 760 mmHg
• Flash Point: 90.6 °C
• Appearance: /
• Density: 0.979 g/cm³
• Vapor Pressure: 0.0303mmHg at 25°C
• Refractive Index: 1.446
• Storage Temp.: Store at RT.
• PKA: 2.48±0.21(Predicted)
• CAS DataBase Reference: N-Methyl-L-leucine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Methyl-L-leucine(3060-46-6)
• EPA Substance Registry System: N-Methyl-L-leucine(3060-46-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 3060-46-6(Hazardous Substances Data)

Usage

Uses

Used in Scientific Research:
N-Methyl-L-leucine is utilized as a research compound for studying protein synthesis and metabolism. Its specific structure allows it to participate in a range of biochemical processes, making it a valuable tool in the field of biochemistry.
Used in Medical or Pharmaceutical Contexts:
While the safety profile and potential applications of N-Methyl-L-leucine in medical or pharmaceutical settings are still under investigation, its unique properties suggest it may have future uses in these areas. As with many compounds primarily used in research, further study is needed to fully understand its potential benefits and risks.
Used in Biochemical Reactions:
N-Methyl-L-leucine is employed as a reactant in various biochemical reactions due to its distinct structure and the presence of the methyl group. This allows it to interact with other molecules in ways that can be harnessed for scientific and potentially therapeutic purposes.

InChI:InChI=1/C7H15NO2/c1-5(2)4-6(8-3)7(9)10/h5-6,8H,4H2,1-3H3,(H,9,10)/t6-/m0/s1

Upstream product

• 1187486-26-5 carriebowmide sulfone 
• 1342309-23-2 trichodepsipeptide A 
• 1342309-24-3 trichodepsipeptide B 
• 1242573-53-0 C₃₅H₅₁N₅O₆S 
• 10034-85-2 hydrogen iodide 
• 64143-96-0 N-methyl-N-tosyl-L-leucine 
• 7647-01-0 hydrogenchloride 
• 108027-39-0 Cyclosporin L 
• 1494680-68-0 ohmyungsamycin A 

Downstream Products

• 879125-40-3 N-(1-acetyl-3-methyl-butyl)-N-methyl-acetamide 
• 90226-69-0 5-methyl-3-methylamino-hexan-2-one 
• 42417-80-1 Z-Ala-MeLeu-OH 
• 3339-45-5 H-L-N-MeLeu-OMe*HCl 
• 1571105-49-1 C₅₇H₈₈N₁₂O₁₀ 
• 1357008-04-8 H-Phe-NMe-Leu-OMe 
• 1357008-65-1 methyl (S)-2-[(S)-2-(tert-butoxycarbonylamino)-N-methyl-3-phenylpropanamido]-4-methylpentanoate 

Relevant articles and documents

Adiponectin-Secretion-Promoting Cyclic Peptide-Polyketide Hybrids from a Halophyte-Associated Fungus, Colletotrichum gloeosporioides JS0417

Three new cyclic peptide-polyketide hybrids (1-3) and two new chaetiacandin-type polyketides (4 and 5) along with nine known compounds were isolated from cultures of a halophyte-associated fungus, Colletotrichum gloeosporioides JS0417. Spectroscopic analysis revealed that 1-3 were cyclic depsipeptides where 3,5,11-trihydroxy-2,6-dimethyldodecanoic acid was linked to two amino acids through amide and ester bonds to form a 12-membered ring. Relative and absolute configurations for the peptides were determined with spectroscopic analysis and chemical reactions. The cyclic depsipeptides 2 and 6 were determined to act as strong adiponectin-secretion-promoting modulators with potential to treat metabolic diseases associated with hypoadiponectinemia. Notably, a known compound, tryptophol, significantly inhibited PGE2synthesis and also promoted adiponectin secretion, exhibiting a similar biological activity profile to aspirin, but with greater potency. The presence of an isoleucine moiety and non-glycosylation may be important for biological activity of the cyclic peptide-polyketide hybrids, and non-methoxylation of the side chain may influence activity of the indole derivatives.

Unique polyhalogenated peptides from the marine sponge Ircinia sp.

Two new bromopyrrole peptides, haloirciniamide A (1) and seribunamide A (2), have been isolated from an Indonesian marine sponge of the genus Ircinia collected in the Thousand Islands (Indonesia). The planar structure of both compounds was assigned on the basis of extensive 1D and 2D NMR spectroscopy and mass spectrometry. The absolute configuration of the amino acid residues in 1 and 2 was determined by the application of Marfey's method. Compound 1 is the first dibromopyrrole cyclopeptide having a chlorohistidine ring, while compound 2 is a rare peptide possessing a tribromopyrrole ring. Both compounds failed to show significant cytotoxicity against four human tumor cell lines, and neither compound was able to inhibit the enzyme topoisomerase I or impair the interaction between programmed cell death protein PD1 and its ligand, PDL1.

Discovery of Amantamide, a Selective CXCR7 Agonist from Marine Cyanobacteria

CXCR7 plays an emerging role in several physiological processes. A linear peptide, amantamide (1), was isolated from marine cyanobacteria, and the structure was determined by NMR and mass spectrometry. The total synthesis was achieved by solid-phase method. After screening two biological target libraries, 1 was identified as a selective CXCR7 agonist. The selective activation of CXCR7 by 1 could provide the basis for developing CXCR7-targeted therapeutics and deciphering the role of CXCR7 in different diseases.

Anti-Cryptococcus Phenalenones and Cyclic Tetrapeptides from Auxarthron pseudauxarthron

Auxarthrones A-E (1-5), five new phenalenones, and two new naturally occurring cyclic tetrapeptides, auxarthrides A (7) and B (8), were obtained from three different solvent extracts of cultures of the coprophilous fungus Auxarthron pseudauxarthron. Auxarthrones C (3) and E (5) possess an unusual 7a,8-dihydrocyclopenta[a]phenalene-7,9-dione ring system that has not been previously observed in natural products. Formation of 1-5 was found to be dependent on the solvent used for culture extraction. The structures of these new compounds were elucidated primarily by analysis of NMR and MS data. Auxarthrone A (1) was obtained as a mixture of chromatographically inseparable racemic diastereomers (1a and 1b) that cocrystallized, enabling confirmation of their structures by X-ray crystallography. The absolute configurations of 7 and 8 were assigned by analysis of their acid hydrolysates using Marfey's method. Compound 1 displayed moderate antifungal activity against Cryptococcus neoformans and Candida albicans, but did not affect human cancer cell lines.

Janadolide, a Cyclic Polyketide-Peptide Hybrid Possessing a tert-Butyl Group from an Okeania sp. Marine Cyanobacterium

Janadolide, a new cyclic polyketide-peptide hybrid possessing a tert-butyl group, was isolated from an Okeania sp. marine cyanobacterium. The gross structure was elucidated by spectroscopic analyses, and the absolute configurations of the amino acid moieties were determined by acid hydrolysis and chiral-phase HPLC analyses. The absolute configuration of the two stereogenic centers in the polyketide moiety was elucidated based on a combination of degradation reactions and spectroscopic analyses including the phenyl-glycine methyl ester method. Janadolide showed potent antitrypanosomal activity with an IC50 value of 47 nM without cytotoxicity against human cells at 10 μM.

Urumamide, a novel chymotrypsin inhibitor with a β-amino acid from a marine cyanobacterium Okeania sp.

Urumamide, a novel cyclic depsipeptide that contains a β-amino acid, was isolated from a marine cyanobacterium Okeania sp. Its gross structure was determined by spectroscopic analyses, and the absolute configuration was established based on Marfey's analyses and chiral HPLC analyses of hydrolysis products. Biologically, urumamide inhibited the growth of human cancer cells. In addition, urumamide inhibited chymotrypsin.

A new cyclic hexapeptide and a new isocoumarin derivative from the marine sponge-associated fungus Aspergillus similanensis KUFA 0013

A new isocoumarin derivative, similanpyrone C (1), a new cyclohexapeptide, similanamide (2), and a new pyripyropene derivative, named pyripyropene T (3) were isolated from the ethyl acetate extract of the culture of the marine sponge-associated fungus Aspergillus similanensis KUFA 0013. The structures of the compounds were established based on 1D and 2D NMR spectral analysis, and in the case of compound 2 the stereochemistry of its amino acid constituents was determined by chiral HPLC analysis of the hydrolysate by co-injection with the D and L amino acids standards. Compounds 2 and 3 were evaluated for their in vitro growth inhibitory activity against MCF-7 (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer) and A373 (melanoma) cell lines, as well as antibacterial activity against reference strains and the environmental multidrug-resistant isolates (MRS and VRE). Only compound 2 exhibited weak activity against the three cancer cell lines, and neither of them showed antibacterial activity.

Ohmyungsamycins A and B: Cytotoxic and antimicrobial cyclic peptides produced by Streptomyces sp. from a volcanic island

Ohmyungsamycins A and B (1 and 2), which are new cyclic peptides, were isolated from a marine bacterial strain belonging to the Streptomyces genus collected from a sand beach on Jeju, a volcanic island in the Republic of Korea. Based on the interpretation of the NMR, UV, and IR spectroscopic and MS data, the planar structures of 1 and 2 were elucidated as cyclic depsipeptides bearing unusual amino acid units, including N-methyl-4-methoxytrytophan, β-hydroxyphenylalanine, and N,N-dimethylvaline. The absolute configurations of the α-carbons of the amino acid residues were determined using the advanced Marfey's method. The configurations of the additional stereogenic centers at the β-carbons of the threonine, N-methylthreonine, and β-hydroxyphenylalanine units were assigned by GITC (2,3,4,6-tetra-O-acetyl- β-d-glucopyranosyl isothiocyanate) derivatization and the modified Mosher's method. We have developed a new method utilizing PGME (phenylglycine methyl ester) derivatization coupled with chromatographic analysis to determine the absolute configuration of N,N-dimethylvaline. Our first successful establishment of the absolute configuration of N,N-dimethylvaline using PGME will provide a general and convenient analytical method for determining the absolute configurations of amino acids with fully substituted amine groups. Ohmyungsamycins A and B showed significant inhibitory activities against diverse cancer cells as well as antibacterial effects.

Isolation, structure elucidation and total synthesis of lajollamide a from the marine fungus Asteromyces cruciatus

The marine-derived filamentous fungus Asteromyces cruciatus 763, obtained off the coast of La Jolla, San Diego, USA, yielded the new pentapeptide lajollamide A (1), along with the known compounds regiolone (2), hyalodendrin (3), gliovictin (4), 1N-norgliovicitin (5), and bis-N-norgliovictin (6). The planar structure of lajollamide A (1) was determined by Nuclear Magnetic Resonance (NMR) spectroscopy in combination with mass spectrometry. The absolute configuration of lajollamide A (1) was unambiguously solved by total synthesis which provided three additional diastereomers of 1 and also revealed that an unexpected acid-mediated partial racemization (2:1) of the L-leucine and L-N-Me-leucine residues occurred during the chemical degradation process. The biological activities of the isolated metabolites, in particular their antimicrobial properties, were investigated in a series of assay systems.

Two new 14-membered cyclopeptide alkaloids from Zizyphus xylopyra

The phytochemical investigation of the bark of Zizyphus xylopyra resulted in the isolation of two new 14-membered ring cyclopeptide alkaloids, xylopyrine-G and xylopyrine H. Their structures have been established by chemical and spectral evidences.