50673-48-8

Basic information

• Product Name: (2R,3S) -3-methyl-2- (methylamino)pentanoic acid
• Synonyms: (2R,3S) -3-methyl-2- (methylamino)pentanoic acid
• CAS NO: 50673-48-8
• Molecular Formula: C7H15NO2
• Molecular Weight: 145.202
• Mol File: 50673-48-8.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: (2R,3S) -3-methyl-2- (methylamino)pentanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S) -3-methyl-2- (methylamino)pentanoic acid(50673-48-8)
• EPA Substance Registry System: (2R,3S) -3-methyl-2- (methylamino)pentanoic acid(50673-48-8)

Safety Data

• Hazardous Substances Data: 50673-48-8(Hazardous Substances Data)

Usage

General Description

(2R,3S)-3-methyl-2-(methylamino)pentanoic acid, also known as D-methylphenylalanine, is a compound with the chemical formula C8H17NO2. It is a chiral amino acid, meaning it has a non-superimposable mirror image, and is commonly found in nature as a building block for proteins. (2R,3S) -3-methyl-2- (methylamino)pentanoic acid has been studied for its potential pharmaceutical applications, such as in the synthesis of new drugs and as a chiral auxiliary in asymmetric synthesis. It is also used as a chemical intermediate in the production of various compounds. Additionally, (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.

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Relevant articles and documents

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).

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.

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.