50673-48-8

Usage

Uses

Used in Pharmaceutical Applications:
(2R,3S)-3-methyl-2-(methylamino)pentanoic acid is used as a chiral auxiliary in asymmetric synthesis for the development of new drugs. Its unique structure allows for the creation of enantiomerically pure compounds, which can have different biological activities and reduce side effects.
Used in Chemical Synthesis:
(2R,3S)-3-methyl-2-(methylamino)pentanoic acid is used as a chemical intermediate in the production of various compounds, such as pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Medical Applications:
(2R,3S)-3-methyl-2-(methylamino)pentanoic acid has been investigated for its potential role in treating various medical conditions, including neurological disorders and mental health issues. Its unique structure and properties may offer new therapeutic options for these conditions.

Upstream product

• 4125-98-8 N-methyl-L-isoleucine 
• 13139-16-7 N-tert-butoxycarbonyl-D-alloisoleucine 
• 1509-35-9 D-alloisoleucine 
• 53462-50-3 N-Boc-(2R,3S)-N-Me-Ile 
• 118904-37-3 N-(9-Fluorenylmethoxycarbonyl)-D-alloisoleucine 
• 1356090-81-7 Fmoc-D-allo-MeIle-OH 
• 50-00-0 formaldehyd 
• 105091-14-3 theonellamine B 
• 3160-59-6 N-benzyloxycarbonyl-L-isoleucine 
• 319-78-8 isoleucine 
• 865-47-4 potassium tert-butylate 
• 74-88-4 methyl iodide 
• 66866-65-7 3-benzyloxycarbonyl-4-(2-methylpropyl)oxazolidin-5-one 
• 3160-59-6 N-benzyloxycarbonyl-isoleucine 

Relevant academic research and scientific papers

Isolation, Structure Determination, and Total Synthesis of Hoshinoamide C, an Antiparasitic Lipopeptide from the Marine Cyanobacterium Caldora penicillata

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).

Iheyamides A-C, Antitrypanosomal Linear Peptides Isolated from a Marine Dapis sp. Cyanobacterium

Iheyamides A (1), B (2), and C (3), new linear peptides, were isolated from a marine Dapis sp. cyanobacterium. Their structures were elucidated by spectroscopic analyses and degradation reactions. Iheyamide A (1) showed moderate antitrypanosomal activities against Trypanosoma brucei rhodesiense and Trypanosoma brucei brucei (IC50 = 1.5 μM), but the other two analogues, iheyamides B (2) and C (3), did not (IC50 > 20 μM, respectively). The structure-activity relationship clarified that an isopropyl-O-Me-pyrrolinone moiety was necessary for the antitrypanosomal activity. Furthermore, the cytotoxicity of 1 against normal human cells, WI-38, was 10 times weaker than its antitrypanosomal activity (IC50 = 18 μM).

Pembamide, a N-methylated linear peptide from a sponge Cribrochalina sp.

A new highly N-methylated linear peptide, pembamide (1), has been isolated from the marine sponge Cribrochalina sp. (family Niphatidae) collected off the coast of Pemba (Tanzania). The planar structure of 1 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 was determined by application of the Advanced Marfey's method. Compound 1 displayed significant cytotoxicity against three human tumor cell lines with GI50values in the micromolar range.

Trichormamides A and B with antiproliferative activity from the cultured freshwater cyanobacterium Trichormus sp. UIC 10339

Two new cyclic lipopeptides, trichormamides A (1) and B (2), were isolated from the cultured freshwater cyanobacterium Trichormus sp. UIC 10339. The strain was obtained from a sample collected in Raven Lake in Northern Wisconsin. The planar structures of trichormamides A (1) and B (2) were determined using a combination of spectroscopic analyses including HRESIMS and 1D and 2D NMR experiments. The absolute configurations of the amino acid residues were assigned by the advanced Marfey's method after acid hydrolysis. Trichormamide A (1) is a cyclic undecapeptide containing two d-amino acid residues (d-Tyr and d-Leu) and one β-amino acid residue (β-aminodecanoic acid). Trichormamide B (2) is a cyclic dodecapeptide characterized by the presence of four nonstandard α-amino acid residues (homoserine, N-methylisoleucine, and two 3-hydroxyleucines) and one β-amino acid residue (β-aminodecanoic acid). Trichormamide B (2) was cytotoxic against MDA-MB-435 and HT-29 cancer cell lines with IC50 values of 0.8 and 1.5 μM, respectively.

Total structure and inhibition of tumor cell proliferation of laxaphycins

From a mixed assemblage of Lyngbya majuscula rich marine cyanobacteria, we isolated a series of cell growth inhibitory cyclic peptides, The structures of the two major components, laxaphycins A (1) and B (2), and of two minor peptides, laxaphycins B2 (3) and B3 (4), were determined by spectroscopic methods and degradative analysis. Absolute configurations of natural and nonproteinogenic amino acids were determined by a combination of hydrolysis, synthesis of noncommercial residues, chemical derivatization, and HPLC analysis. The organism producing the laxaphycins was identified as the cyanobacterium Anabaena torulosa. The antiproliferative activity of laxaphycins was investigated on a panel of solid and lymphoblastic cancer cells. Our results demonstrate that in contrast to laxaphycin A, laxaphycin B inhibits the proliferation of sensitive and resistant human cancer cell lines and that this activity is strongly increased in the presence of laxaphycin A. This effect appears to be due to an unusual biological synergism.

Highly N-methylated linear peptides produced by an atypical sponge-derived Acremonium sp.

RHM1 (1) and RHM2 (2) are highly N-methylated linear octapeptides produced by an atypical strain of Acremonium sp., cultured from a marine sponge collected in Papua New Guinea. The known peptaibiotic efrapeptin G (3) was also isolated from this fungus. The planar structures of 1 and 2 were assigned based on 1D- and 2D-NMR experiments and fragmentation patterns from ESIMS. The absolute configuration of 1 was determined via Marfey's method; the absolute configuration of 2 is proposed to be identical. Efrapeptin G (3) displayed potent cytotoxicity against murine cancer cell lines, while RHM1 (1) and RHM2 (2) showed weak cytotoxicity against murine cancer cell lines; efrapeptin G (3) and RHM1 (1) also demonstrated antibacterial activity.

Determination of the complete absolute configuration of petriellin A

We report the full structural determination of the depsipeptide petriellin A. The absolute configuration of the amino acid residues, N-methyl isoleucine and N-methyl threonine, have been determined by a combination of HPLC and TLC comparison of synthetic Marfey's derivatives and Marfey's derivatives of the natural product hydrolysate. The configuration of the chiral centres in these two N-methylated residues was found to be the same as those of the common unmethylated l-amino acids. CSIRO 2006.

Preparation of N-Z-protected N-methylated amino acids

A process for preparing N-protected N-alkylated amino acids of the formula I: in which the substituents have the meanings stated in the description, comprises mixing a compound of the formula II with a solution of potassium tert-butanolate in a non-protic organic solvent, and subsequently adding a C1-2-alkyl halide.

New cyclic peptides from the Indonesian sponge Theonella swinhoei

Three new cyclic peptides, barangamides B, C, and D and a new depsipeptide, theonellapeptolide IIe as well as known theonellapeptolides Ia, Id, Ie, IId have been isolated from the sponge Theonella swinhoei collected in Baranglompo Island, Indonesia The structures of barangamides were elucidated by interpretation of NMR data and application of Marfey's method. The structure of theonellapeptolide IIe, a mixture of several conformers showing complex NMR spectra, was determined by MS analysis of a ring-opened product and by chemical reaction. Some of the theonellapeptolides showed mild immunosuppressive activity, while barangamide A was inactive. (C) 2000 Elsevier Science Ltd.

Substituted quinoxaline-2-ones as glutamate receptor antagonists

A novel series of substituted quinoxaline 2-ones useful as neuroprotective agents are taught. Novel intermediates, processes of preparation, and pharmaceutical compositions containing the compounds are also taught. The compounds are glutamate receptor antagonists and are useful in the treatment of stroke, cerebral ischemia, or cerebral infarction resulting from thromboembolic or hemorrhagic stroke, cerebral vasospasms, hypoglycemia, cardiac arrest, status epilepticus, perinatal asphyxia, anoxia, seizure disorders, pain, Alzheimer's, Parkinson's, and Huntington's Diseases.