899900-52-8

Usage

Uses

Used in Pharmaceutical Synthesis:
(R)-2-(diMethylaMino)-3-Methylbutanoic acid is used as a chiral auxiliary for the synthesis of various pharmaceuticals and biologically active compounds. Its unique structure and properties facilitate the production of enantiomerically pure compounds, which are essential for the development of effective and safe medications.
Used in Organic Chemistry Research:
In the field of organic chemistry, (R)-2-(diMethylaMino)-3-Methylbutanoic acid serves as a valuable chiral auxiliary for asymmetric synthesis and the preparation of enantiomerically pure compounds. Its presence can influence the stereochemistry of reactions, enabling the selective formation of desired enantiomers.
Used in Chiral Catalysts:
(R)-2-(diMethylaMino)-3-Methylbutanoic acid can be employed as a chiral catalyst in various chemical reactions, promoting enantioselective transformations. Its ability to induce chirality in the products can be harnessed to obtain enantiomerically enriched compounds, which are crucial in the synthesis of pharmaceuticals and agrochemicals.
Used in Analytical Chemistry:
As a chiral compound, (R)-2-(diMethylaMino)-3-Methylbutanoic acid can be utilized in the development of chiral stationary phases for chromatographic separations. This allows for the resolution of enantiomers, which is vital for the analysis and purification of chiral compounds in various industries, including pharmaceuticals and food science.
Used in the Production of Chiral Building Blocks:
(R)-2-(diMethylaMino)-3-Methylbutanoic acid can be used as a chiral building block in the synthesis of complex organic molecules. Its unique structure and chiral properties make it a valuable component in the construction of chiral molecules with specific biological activities or desired physical properties.

Upstream product

• 50-00-0 formaldehyd 
• 640-68-6 D-Val-OH 
• 186581-53-3 diazomethane 
• 88930-14-7 (-)-α-methylamino-β-methylbutyric acid 

Downstream Products

• 1105044-33-4 (S)-{(1S,2S)-2-[(R)-2-(dimethylamino)-3-methylbutanoyloxy]-1,2-diphenylethyl}-2-(dimethylamino)-3-methylbutanoate 
• 1334671-81-6 (R)-N'-benzyl 2-(N,N-dimethylamino)-3-methylbutanamide 

Relevant academic research and scientific papers

Ochraceopetalin, a mixed-biogenetic salt of polyketide and amino acid origins from a marine-derived aspergillus ochraceopetaliformis fungus

Ochraceopetalin (1), a mixed-biogenetic salt compound and its component 2 were isolated from the culture broths of a marine-derived fungus, Aspergillus ochraceopetaliformis. Based on combined spectroscopic and chemical analyses, the structure of 1 was determined to be a sulfonated diphenylether-aminol-amino acid ester guanidinium salt of an unprecedented structural class, while 2 was determined to be the corresponding sulfonated diphenylether. Ochraceopetaguanidine (3), the other guanidine-bearing aminol amino acid ester component, was also prepared and structurally elucidated. Compound 1 exhibited significant cytotoxicity against K562 and A549 cells.

Pagoamide A, a Cyclic Depsipeptide Isolated from a Cultured Marine Chlorophyte, Derbesia sp., Using MS/MS-Based Molecular Networking

A thiazole-containing cyclic depsipeptide with 11 amino acid residues, named pagoamide A (1), was isolated from laboratory cultures of a marine Chlorophyte, Derbesia sp. This green algal sample was collected from America Samoa, and pagoamide A was isolated using guidance by MS/MS-based molecular networking. Cultures were grown in a light- and temperature-controlled environment and harvested after several months of growth. The planar structure of pagoamide A (1) was characterized by detailed 1D and 2D NMR experiments along with MS and UV analysis. The absolute configurations of its amino acid residues were determined by advanced Marfey's analysis following chemical hydrolysis and hydrazinolysis reactions. Two of the residues in pagoamide A (1), phenylalanine and serine, each occurred twice in the molecule, once in the d- and once in the l-configuration. The biosynthetic origin of pagoamide A (1) was considered in light of other natural products investigations with coenocytic green algae.

Heptavalinamide A, an Extensively N-Methylated Linear Nonapeptide from a Cyanobacterium Symploca sp. And Development of a Highly Sensitive Analysis of N, N-Dimethylvaline by LCMS

An extensively N-methylated linear nonapeptide heptavalinamide A (1) was isolated from the marine cyanobacterium Symploca sp. collected at Kabira Reef of Ishigaki Island, Okinawa. The amino acid sequence of 1 was assigned by interpretation of 2D NMR and MS/MS data. The absolute configurations of the constituent amino acids were determined by the application of Marfey's method. A method to assign the configuration of N,N-dimethylvaline by LCMS is discussed.

Lyngbyabellins K-N from two Palmyra atoll collections of the marine cyanobacterium Moorea bouillonii

Five lipopeptides of the lyngbyabellin structure class, four cyclic (1-3 and 5) and one linear (4), were isolated from the extracts of two collections of filamentous marine cyanobacteria obtained from the Palmyra Atoll in the Central Pacific Ocean. Their

Defining the structural parameters that confer anticonvulsant activity by the site-by-site modification of (R)-N′-benzyl 2-amino-3-methylbutanamide

Primary amino acid derivatives (PAADs) (N′-benzyl 2-substituted 2-amino acetamides) are structurally related to functionalized amino acids (FAAs) (N′-benzyl 2-substituted 2-acetamido acetamides) but differ by the absence of the terminal N-acetyl group. Both classes exhibit potent anticonvulsant activities in the maximal electroshock seizure animal model, and the reported structure-activity relationships (SARs) of PAADs and FAAs differ in significant ways. Recently, we documented that PAAD efficacy was associated with a hydrocarbon moiety at the C(2)-carbon, while in the FAAs, a substituted heteroatom one atom removed from the C(2)-center was optimal. Previously in this issue, we showed that PAAD activity was dependent upon the electronic properties of the 4′-N′-benzylamide substituent, while FAA activity was insensitive to electronic changes at this site. In this study, we prepared analogues of (R)-N′-benzyl 2-amino-3-methylbutanamide to identify the structural components for maximal anticonvulsant activity. We demonstrated that the SAR of PAADs and FAAs diverged at the terminal amide site and that PAADs had considerably more structural latitude in the types of units that could be incorporated at this position, suggesting that these compounds function according to different mechanism(s).

Coibamide A, a potent antiproliferative cyclic depsipeptide from the panamanian marine cyanobacterium Leptolyngbya sp.

Coibamide A (1) is a new, potent antiproliferative depsipeptide which was isolated from a marine Leptolyngbya cyanobacterium collected from the Coiba National Park, Panama. The planar structure of 1 was elucidated by a combination of NMR spectroscopy and mass spectrometry. Exhaustive 1D and 2D NMR spectroscopy included natural abundance 15N and variable temperature experiments; mass spectrometry included TOF-ESI-MSn and FT-MSn experiments. Chemical degradation followed by chiral HPLC- and GC-MS analyses was used to assign the absolute configuration of 1. This highly methylated cyclized depsipeptide exhibited an unprecedented selectivity profile in the NCI 60 cancer cell line panel and appears to act via a novel mechanism. Copyright