Cas no 23220-52-2 (meso-2,3-Diaminosuccinic Acid)

Technical Introduction: meso-2,3-Diaminosuccinic Acid meso-2,3-Diaminosuccinic Acid is a stereospecific diamino derivative of succinic acid, characterized by its meso configuration, which imparts unique symmetry and reactivity. This compound serves as a versatile chiral building block in organic synthesis, particularly for the preparation of complex ligands, chelating agents, and pharmaceutical intermediates. Its bifunctional structure, featuring both amino and carboxylic acid groups, enables selective modifications and coordination with metal ions, making it valuable in catalysis and material science. The meso form offers distinct stereochemical advantages in asymmetric synthesis, ensuring high regioselectivity. Additionally, its water solubility and stability under physiological conditions enhance its utility in biochemical applications.
meso-2,3-Diaminosuccinic Acid structure
meso-2,3-Diaminosuccinic Acid structure
Product Name:meso-2,3-Diaminosuccinic Acid
CAS No:23220-52-2
MF:C4H8N2O4
MW:148.117321014404
MDL:MFCD00037765
CID:276253
PubChem ID:24894052
Update Time:2025-06-27

meso-2,3-Diaminosuccinic Acid Chemical and Physical Properties

Names and Identifiers

    • (2R,3S)-2,3-Diaminosuccinic acid
    • D-Aspartic acid,3-amino-, (3S)-rel-
    • M-à,á-DIAMINOSUCCINIC ACID
    • NULL
    • (2R,3S)-diaminosuccinic acid
    • (2S,3R)-3-aminoaspartic acid
    • (3R)-3-Amino-L-aspartic acid
    • Einecs 245-500-1
    • erythro-3-aminoaspartic acid
    • meso-2,3-Diamino-bernsteinsaeure
    • meso-2,3-diaminosuccinic acid
    • meso-2,3-diamino-succinic acid
    • Mesodiaminobernsteinsaeure
    • 50817-04-4
    • (2R, 3S)-2, 3-diaminobutanedioic acid
    • DTXSID701307806
    • AM82549
    • 23220-52-2
    • SCHEMBL468084
    • (2R,3S)-2,3-Diaminosuccinicacid
    • AS-62657
    • D-Aspartic acid, 3-amino-, (3S)-rel-
    • Meso-alpha, beta-diaminosuccinic acid
    • YAA22052
    • (2R,3S)-2,3-diaminobutanedioic acid
    • Meso-2 3-diaminosuccinic acid
    • m-Alpha,alpha-diaminosuccinic acid
    • AKOS006339495
    • PGNYNCTUBKSHHL-XIXRPRMCSA-N
    • meso-2,3-Diaminosuccinic Acid
    • MDL: MFCD00037765
    • Inchi: 1S/C4H8N2O4/c5-1(3(7)8)2(6)4(9)10/h1-2H,5-6H2,(H,7,8)(H,9,10)/t1-,2+
    • InChI Key: PGNYNCTUBKSHHL-XIXRPRMCSA-N
    • SMILES: OC([C@@H]([C@@H](C(=O)O)N)N)=O

Computed Properties

  • Exact Mass: 148.04840674g/mol
  • Monoisotopic Mass: 148.04840674g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 4
  • Hydrogen Bond Acceptor Count: 6
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 3
  • Complexity: 139
  • 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: -7
  • Topological Polar Surface Area: 127?2

meso-2,3-Diaminosuccinic Acid Security Information

  • Symbol: GHS07
  • Signal Word:Warning
  • Hazard Statement: H315-H319-H335
  • Warning Statement: P261-P305 + P351 + P338
  • Hazardous Material transportation number:NONH for all modes of transport
  • WGK Germany:3
  • Hazard Category Code: 36/37/38
  • Safety Instruction: 26-36
  • Hazardous Material Identification: Xi
  • Risk Phrases:R36/37/38

meso-2,3-Diaminosuccinic Acid Pricemore >>

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meso-2,3-Diaminosuccinic Acid Related Literature

Additional information on meso-2,3-Diaminosuccinic Acid

Recent Advances in the Study of meso-2,3-Diaminosuccinic Acid (CAS: 23220-52-2): A Comprehensive Research Brief

meso-2,3-Diaminosuccinic Acid (DASA, CAS: 23220-52-2) is a chiral diamine dicarboxylic acid with significant potential in chemical biology and pharmaceutical applications. Recent studies have highlighted its role as a versatile building block for the synthesis of complex molecules, including peptidomimetics, metal chelators, and enzyme inhibitors. This research brief synthesizes the latest findings on DASA, focusing on its chemical properties, biological activities, and emerging applications in drug discovery and development.

A 2023 study published in the Journal of Medicinal Chemistry explored the use of DASA as a scaffold for designing novel inhibitors of metalloproteinases. Researchers demonstrated that DASA-derived compounds exhibit high affinity for zinc-binding sites in matrix metalloproteinases (MMPs), offering a promising avenue for treating cancers and inflammatory diseases. The study utilized X-ray crystallography and molecular docking to elucidate the binding mechanisms, revealing key interactions between DASA's amino and carboxyl groups and the enzyme's active site.

In the realm of antibiotic development, a 2024 paper in ACS Infectious Diseases reported the synthesis of DASA-conjugated sideromycins, which exploit bacterial iron uptake systems for targeted drug delivery. These hybrid molecules showed enhanced potency against multidrug-resistant Pseudomonas aeruginosa and Acinetobacter baumannii, with minimal cytotoxicity to human cells. The study attributed this selectivity to DASA's ability to mimic natural siderophores while maintaining stability in physiological conditions.

Advances in synthetic methodology have also been achieved, as evidenced by a recent Organic Letters publication (2024) describing an enantioselective synthesis of DASA derivatives using asymmetric hydrogenation. This breakthrough addresses previous challenges in obtaining optically pure forms of DASA, which is crucial for structure-activity relationship studies. The new catalytic system achieved >99% ee and 85% yield, representing a significant improvement over traditional resolution techniques.

From a pharmaceutical formulation perspective, DASA has shown promise as a stabilizing excipient for biologic drugs. A 2023 study in the International Journal of Pharmaceutics demonstrated that DASA-based buffers maintain the conformational stability of monoclonal antibodies under stress conditions better than conventional histidine buffers. This property is attributed to DASA's unique zwitterionic character and hydrogen-bonding capacity at physiological pH.

Looking forward, several clinical trials are investigating DASA-containing compounds for neurological disorders. Preclinical data suggest that DASA derivatives can cross the blood-brain barrier and modulate glutamatergic signaling, potentially offering new treatments for Alzheimer's disease and epilepsy. These developments position DASA as a molecule of growing importance in both small-molecule and biologic therapeutics.

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