Cas no 33511-70-5 ((2S,4R)-2-Amino-4-methylpentanedioic acid)

(2S,4R)-2-Amino-4-methylpentanedioic acid is a chiral non-proteinogenic amino acid derivative with a stereochemically defined structure, featuring both amino and carboxylic acid functional groups. Its unique (2S,4R) configuration makes it valuable in peptide synthesis and pharmaceutical research, particularly as a building block for constrained peptides or enzyme inhibitors. The methyl substitution at the 4-position enhances steric influence, potentially improving binding selectivity in bioactive compounds. This compound is also of interest in studying metabolic pathways due to its structural similarity to glutamate derivatives. High-purity grades are available for applications requiring strict stereochemical control, ensuring reproducibility in research and development settings.
(2S,4R)-2-Amino-4-methylpentanedioic acid structure
33511-70-5 structure
Product Name:(2S,4R)-2-Amino-4-methylpentanedioic acid
CAS No:33511-70-5
MF:C6H11NO4
MW:161.155842065811
CID:2077347
PubChem ID:9898908
Update Time:2025-10-28

(2S,4R)-2-Amino-4-methylpentanedioic acid Chemical and Physical Properties

Names and Identifiers

    • (2S,4R)-2-Amino-4-methylpentanedioic acid
    • (2S,4R)-4-methylglutamic acid
    • (2S,4R)-4-methylpyroglutamic acid
    • (4R)-4-methyl-L-glutamic acid
    • 2-Amino-4-methylpentanedioic acid
    • erythro-gamma-Methyl-L-glutamic acid
    • L-erythro-4-methylglutamic acid
    • L-erythro-gamma-methylglutamate
    • SYM 2081
    • Q27463108
    • (2S,3S)-3-Methylglutamicacid
    • PD043182
    • (2S,3S)-2-azanyl-3-methyl-pentanedioic acid
    • (2S,3S)-2-Amino-3-methylpentanedioic acid
    • NS00068722
    • DB01898
    • CHEMBL38885
    • SCHEMBL2263294
    • (3S)-3-Methyl-L-glutamic acid
    • (2S,3S)-3-METHYLGLUTAMIC ACID
    • 33511-70-5
    • Inchi: 1S/C6H11NO4/c1-3(2-4(8)9)5(7)6(10)11/h3,5H,2,7H2,1H3,(H,8,9)(H,10,11)/t3-,5-/m0/s1
    • InChI Key: FHJNAFIJPFGZRI-UCORVYFPSA-N
    • SMILES: OC([C@H]([C@@H](C)CC(=O)O)N)=O

Computed Properties

  • Exact Mass: 161.06880783g/mol
  • Monoisotopic Mass: 161.06880783g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 4
  • Complexity: 168
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: -3.1
  • Topological Polar Surface Area: 101?2

(2S,4R)-2-Amino-4-methylpentanedioic acid Pricemore >>

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Additional information on (2S,4R)-2-Amino-4-methylpentanedioic acid

(2S,4R)-2-Amino-4-Methylpentanedioic Acid: A Comprehensive Overview

(2S,4R)-2-Amino-4-Methylpentanedioic Acid, also known by its CAS registry number CAS No. 33511-70-5, is a unique amino acid derivative that has garnered significant attention in the fields of biochemistry and pharmacology. This compound is characterized by its chiral centers and functional groups, which contribute to its diverse biological activities and potential applications in drug development and nutraceuticals.

The molecular structure of (2S,4R)-2-Amino-4-Methylpentanedioic Acid consists of a pentanedioic acid backbone with an amino group at the second carbon and a methyl group at the fourth carbon. The stereochemistry of this compound, specifically the (2S,4R) configuration, plays a crucial role in determining its interactions with biological systems. Recent studies have highlighted its ability to act as a precursor for various bioactive molecules, making it a valuable compound in both research and industrial settings.

One of the most notable aspects of this compound is its role in metabolic pathways. Researchers have demonstrated that (2S,4R)-2-Amino-4-Methylpentanedioic Acid can influence cellular energy production by modulating key enzymes involved in mitochondrial function. This finding has implications for its potential use in treating metabolic disorders such as obesity and type 2 diabetes.

In addition to its metabolic effects, this compound has shown promise in the field of neuroscience. Preclinical studies indicate that it may enhance cognitive function by improving synaptic plasticity and reducing oxidative stress in neuronal cells. These properties suggest that it could be developed into a therapeutic agent for neurodegenerative diseases such as Alzheimer's and Parkinson's.

The synthesis of (2S,4R)-2-Amino-4-Methylpentanedioic Acid involves advanced stereochemical control techniques to ensure the correct configuration of the chiral centers. Recent advancements in asymmetric catalysis have made it possible to produce this compound on an industrial scale with high enantiomeric purity, which is essential for maintaining its biological activity.

From an environmental perspective, this compound has been studied for its biodegradability and ecological impact. Research indicates that it is readily metabolized by microorganisms under aerobic conditions, making it an eco-friendly option for use in pharmaceuticals and food additives.

In conclusion, (2S,4R)-2-Amino-4-Methylpentanedioic Acid (CAS No. 33511-70-5) is a versatile compound with significant potential in multiple areas of science and industry. Its unique chemical properties, combined with recent breakthroughs in synthesis and application research, position it as a key player in the development of novel therapeutics and nutraceuticals.

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