16422-27-8

Basic information

• Product Name: (R)-dimethyl 2-aminopentanedioate
• Synonyms: (R)-dimethyl 2-aminopentanedioate
• CAS NO: 16422-27-8
• Molecular Formula: C₇H₁₃NO₄
• Molecular Weight: 175.18242
• Mol File: 16422-27-8.mol
• Article Data: 50

Chemical Properties

• Boiling Point: 224.3±25.0 °C(Predicted)
• Appearance: /
• Density: 1.129±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 6.90±0.35(Predicted)
• CAS DataBase Reference: (R)-dimethyl 2-aminopentanedioate(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-dimethyl 2-aminopentanedioate(16422-27-8)
• EPA Substance Registry System: (R)-dimethyl 2-aminopentanedioate(16422-27-8)

Safety Data

• Hazardous Substances Data: 16422-27-8(Hazardous Substances Data)

Usage

General Description

(R)-dimethyl 2-aminopentanedioate, also known as R(-)-N-acetyl-lysine, is an organic compound belonging to the class of amino acid derivatives. It is a chiral molecule, with a specific optical rotation, and is commonly used in the synthesis of pharmaceuticals and other bioactive compounds. This chemical has applications in the pharmaceutical and healthcare industries, particularly in the development of medications for various medical conditions. Additionally, (R)-dimethyl 2-aminopentanedioate has been studied for its potential role in regulating cellular metabolism and as a precursor for the synthesis of various bioactive compounds. Overall, this chemical compound is of interest for its potential therapeutic applications and its role in the development of various pharmaceutical products.

Upstream product

• 186581-53-3 diazomethane 
• 617-65-2 Glutamic acid 
• 56-86-0 L-glutamic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 67-56-1 methanol 
• 6893-26-1 D-Glutamic acid 
• 124-41-4 sodium methylate 
• 67436-17-3 benzyloxycarbonylglutamic acid dimethyl ester 
• 109918-30-1 3-((2R,5S)-5-Isopropyl-3,6-dimethoxy-2,5-dihydro-pyrazin-2-yl)-propionic acid methyl ester 
• 23150-65-4 L-glutamic dimethyl ester hydrochloride 
• 1420845-87-9 6-hydroxymetatacarboline B 
• 1420845-95-9 metatacarboline B 
• 1499-55-4 L-glutamic acid 5-methyl ester 
• 75-77-4 chloro-trimethyl-silane 

Downstream Products

• 4931-66-2 methyl (S)-pyroglutamate 
• 61298-97-3 C₁₆H₂₀N₂O₇S 
• 118459-77-1 Bz-Leu-Glu-di-OMe 
• 27169-29-5 Bz-Glu-γ-OMe-Glu-γ-OMe-OMe 
• 118459-73-7 Bz-Glu(α-OMe)-Glu-di-OMe 
• 128254-58-0 Bz-Glu(α-OMe)-Glu-di-OMe 
• 21946-71-4 (2S)-aminopentan-1,5-diol 
• 79701-06-7 (R)-2-((S)-6-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-hexanoylamino)-pentanedioic acid dimethyl ester 
• 79701-04-5 (R)-2-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-pentanedioic acid dimethyl ester 
• 2361-99-1 N-Acetyl-L-glutaminsaeure-dimethylester 
• 158109-41-2 3-O-<2-O--N-(β-D-glucopyranosyluronyl)-L-glutamic acid methyl ester>(3β,20β)-11-oxo-30-(N-carbonyl-L-glutamic acid methyl ester)-30-norolean-12-ene 
• 100176-26-9 Z-L-Ala(CN)-L-Glu(OCH₃)-OCH₃ 
• 166756-72-5 N-(4-nitrobenzoyl)-D-glutamic acid dimethyl ester 
• 176208-40-5 dimethyl N-<4-<2-(2,4-diaminothieno<2,3-d>pyrimidin-5-yl)ethyl>benzoyl>-L-glutamate 

Relevant articles and documents

Low mass MS/MS fragments of protonated amino acids used for distinction of their 13C- isotopomers in metabolic studies

Glu, Gln, Pro, and Ala are the main amino acids involved in ammonia detoxification in mosquitoes. In order to develop a tandem mass spectrometry method (MS2) to monitor each carbon of the above isotopically-labeled 13C-amino acids for metabolic studies, the compositions and origins of atoms in fragments of the protonated amino acid should be first elucidated. Thus, various electrospray (ESI)-based MS2 tools were employed to study the fragmentation of these unlabeled and isotopically-labeled amino acids and better understand their dissociation pathways. A broad range of fragments, including previously-undescribed low m/z fragments was revealed. The formulae of the fragments (from m/z 130 down to m/z 27) were confirmed by their accurate masses. The structures and conformations of the larger fragments of Glu were also explored by ion mobility mass spectrometry (IM-MS) and gas-phase hydrogen/deuterium exchange (HDX) experiments. It was found that some low m/z fragments (m/z 27-30) are common to Glu, Gln, Pro, and Ala. The origins of carbons in these small fragments are discussed and additional collision induced dissociation (CID) MS2 fragmentation pathways are proposed for them. It was also found that small fragments (≤m/z 84) of protonated, methylated Glu, and methylated Gln are the same as those of the underivatized Glu and Gln. Taken together, the new approach of utilizing low m/z fragments can be applied to distinguish, identify, and quantify 13C-amino acids labeled at various positions, either in the backbone or side chain. [Figure not available: see fulltext.]

Alkaloids from the mushroom pseudobaeospora pyrifera, pyriferines A-C

Three novel alkaloids (1-3), named pyriferines A-C, were isolated from fruiting bodies of Pseudobaeospora pyrifera. They possess an unusual eight-membered N/O-acetal ring, derived from L-glutamic acid, that is connected to an enolized 1,3-diketo moiety. The structures were determined by spectroscopic methods, and the absolute configuration of the glutamic acid moiety was established using GC-MS after Mosher-type derivatization.

Nematicidal anthranilic acid derivatives from Laccaria species

Three undescribed natural products, the anthranilic acid derivatives laccanthrilic acids A, B, and C, as well as the known (3S)-1,2,3,4-tetrahydro-3-β-carboline-3-carboxylic acid were isolated from fruiting bodies of Laccaria laccata. The structures were established by 1D and 2D NMR spectroscopy, HR-(+)-ESIMS and chemical synthesis. The absolute configuration of laccanthrilic acids A and B was determined by GC-MS after hydrolytic cleavage and derivatisation of the resulting glutamic acid with methanol and Mosher's reagent and subsequent comparison with authentic synthetic samples of known absolute configuration. The absolute configuration of laccanthrilic acid C was determined by comparison of the CD spectra of laccanthrilic acids B and C with each other. Metabolic profiling of related species showed that the compounds are common in the genus Laccaria. Laccanthrilic acid B exhibited moderate nematicidal effects against Caenorhabditis elegans, which might explain to some degree the beneficial role of these fungi for the growth and survival of their host plants.

A General Stereocontrolled Synthesis of Opines through Asymmetric Pd-Catalyzed N-Allylation of Amino Acid Esters

A stereo-divergent synthesis of natural and unnatural opines in stereochemically pure form is based on the direct palladium-catalyzed N-allylation of α-amino acid esters (up to 97 % ee or 99 : 1 d.r.) using methyl (E)-2-penten-4-yl carbonate in the presence of only 1 mol% of a catalyst, prepared in-situ from the C2-symmetric diphosphine iPr-MediPhos and [Pd(allyl)Cl]2. Selected target compounds (incl. a derivative of the drug enalapril) were efficiently obtained from the N-allylated intermediates by oxidative cleavage (ozonolysis) of the allylic C=C bond under temporary N-Boc-protection.

N-Pyrazinoyl substituted amino acids as potential antimycobacterial agents-the synthesis and biological evaluation of enantiomers

Tuberculosis is an infectious disease caused by Mycobacterium tuberculosis (Mtb), each year causing millions of deaths. In this article, we present the synthesis and biological evaluations of new potential antimycobacterial compounds containing a fragment of the first-line antitubercular drug pyrazinamide (PZA), coupled with methyl or ethyl esters of selected amino acids. The antimicrobial activity was evaluated on a variety of (myco)bacterial strains, including Mtb H37Ra, M. smegmatis, M. aurum, Staphylococcus aureus, Pseudomonas aeruginosa, and fungal strains, including Candida albicans and Aspergillus flavus. Emphasis was placed on the comparison of enantiomer activities. None of the synthesized compounds showed any significant activity against fungal strains, and their antibacterial activities were also low, the best minimum inhibitory concentration (MIC) value was 31.25 μM. However, several compounds presented high activity against Mtb. Overall, higher activity was seen in derivatives containing l-amino acids. Similarly, the activity seems tied to the more lipophilic compounds. The most active derivative contained phenylglycine moiety (PC-d/l-Pgl-Me, MIC 1.95 μg/mL). All active compounds possessed low cytotoxicity and good selectivity towards Mtb. To the best of our knowledge, this is the first study comparing the activities of the d- and l-amino acid derivatives of pyrazinamide as potential antimycobacterial compounds.