L-Methionine sulfoximine (MSX) - Moligand™, ≥98% , CAS No.15985-39-4

CAS: 15985-39-4 Cat. No.: M111096 Molecular Weight: 180.23 Beilstein Registry Number: 6175446 EC Number: 629-483-1

GRADE & PURITY Moligand™, ≥98%

Synonyms

(2S)-2-Amino-4-(S-methylsufonimidoyl)butanoic acid | (2S)-2-Amino-4-(S-methylsufonimidoyl)-butanoic acid | (E)-3-pyridin-3-ylprop-2-enoic acid | NCGC00094132-04 | MFCD00002621 | AKOS015892783 | L-Methionine sulfoximine | M 5379 | Prestwick0_000523 | SPBio

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

L-Methionine [R,S]-Sulfoximine inhibits both γGCS g-glutamylcysteine synthetase and Gl Syn (glutamine synthetase). Working concentrations for inhibition of g-glutamylcysteine synthetase are 0.2-2.0 mM (52% inhibition occured at 100 mM).

Specifications

Synonyms

(2S)-2-Amino-4-(S-methylsufonimidoyl)butanoic acid | (2S)-2-Amino-4-(S-methylsufonimidoyl)-butanoic acid | (E)-3-pyridin-3-ylprop-2-enoic acid | NCGC00094132-04 | MFCD00002621 | AKOS015892783 | L-Methionine sulfoximine | M 5379 | Prestwick0_000523 | SPBio

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

L-Methionine sulfoximine (MSX) enhances NH3 production in seedling leaves wheat, barley, corn and sorghum plants by inhibiting glutamine synthetase (GS) activity. Methionine sulfoximine (MSX) increases ornithine decarboxylase activity, decreases the survi

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

INHIBITOR

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488186540
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488186540
• Canonical Smiles: CS(=N)(=O)CCC(C(=O)O)N
• IUPAC Name: (2S)-2-amino-4-(methylsulfonimidoyl)butanoic acid
• InChIKey: SXTAYKAGBXMACB-DPVSGNNYSA-N
• INCHI: 1S/C5H12N2O3S/c1-11(7,10)3-2-4(6)5(8)9/h4,7H,2-3,6H2,1H3,(H,8,9)/t4-,11?/m0/s1
• Isomeric SMILES: CS(=N)(=O)CC[C@@H](C(=O)O)N
• WGK Germany: 3
• Molecular Weight: 180.23
• Beilstein: 6175446
• Reaxy-Rn: 1725509
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1725509&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives
            • Level7 Alpha amino acids
              • Level8 L-alpha-amino acids

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives - Alpha amino acids and derivatives - Alpha amino acids
• Direct Parent: L-alpha-amino acids
• Alternative Parents: Thia fatty acids Carbo-azosulfones Amino acids Monocarboxylic acids and derivatives Carboxylic acids Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: L-alpha-amino acid - Thia fatty acid - Fatty acid - Fatty acyl - Carbo-azosulfone - Amino acid - Carboxylic acid - Monocarboxylic acid or derivatives - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Primary amine - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Amine - Primary aliphatic amine - Carbonyl group - Organic oxide - Hydrocarbon derivative - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
• External Descriptors: non-proteinogenic L-alpha-amino acid - L-methionine derivative - methionine sulfoximine

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: DMSO: <1.8 mg/mL (10 mM)
• Melt Point(°C): 210°C
• Molecular Weight: 180.230 g/mol
• XLogP3: -1.800
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 180.057 Da
• Monoisotopic Mass: 180.057 Da
• Topological Polar Surface Area: 113.000 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 244.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Bin Du, Qingqing Jiao, Yimeng Bai, Min Yu, Mengxue Pang, Mengmeng Zhao, Huizhen Ma, Hanchun Yao.  (2022)  Glutamine Metabolism-Regulated Nanoparticles to Enhance Chemoimmunotherapy by Increasing Antigen Presentation Efficiency.  ACS Applied Materials & Interfaces,      [PMID:35138815] [10.1021/acsami.1c21417]

2. Xinchong Shi, Xiangsong Zhang, Chang Yi, Yubo Liu, Qiao He.  (2015)  [13N]Ammonia Positron Emission Tomographic/Computed Tomographic Imaging Targeting Glutamine Synthetase Expression in Prostate Cancer.  Molecular Imaging,      [PMID:25431095] [10.2310/7290.2014.00048]