β-Aspartylaspartic acid
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β-Aspartylaspartic acid

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An impurity of L-Ornithine L-aspartate salt which is used as a ligand in targeting SDF-1/CXCL12 with ligands that prevents activation of CXCR4 through structure-based drug design.

Category
Others
Catalog number
BAT-009105
CAS number
60079-22-3
Molecular Formula
C8H12N2O7
Molecular Weight
248.19
β-Aspartylaspartic acid
IUPAC Name
2-[(3-amino-3-carboxypropanoyl)amino]butanedioic acid
Synonyms
Ornithine aspartate-2; Ornithine aspartate impurity B; L-Ornithine L-Aspartate Impurity 2; beta-Asp-Asp; (2S)-2-[[(3S)-3-amino-3-carboxypropanoyl]amino]butanedioic acid; ((S)-3-amino-3-carboxypropanoyl)-L-aspartic acid
Appearance
White to Off-white Solid
Density
1.6±0.1 g/cm3
Melting Point
152-153°C
Boiling Point
594.1±50.0 °C at 760 mmHg
Sequence
H-Asp-Asp-OH
Solubility
Soluble in DMSO
InChI
InChI=1S/C8H12N2O7/c9-3(7(14)15)1-5(11)10-4(8(16)17)2-6(12)13/h3-4H,1-2,9H2,(H,10,11)(H,12,13)(H,14,15)(H,16,17)
InChI Key
KXAWLANLJYMEGB-UHFFFAOYSA-N
Canonical SMILES
C(C(C(=O)O)N)C(=O)NC(CC(=O)O)C(=O)O
1. Super Brønsted acid catalysis
Cheol Hong Cheon, Hisashi Yamamoto Chem Commun (Camb) . 2011 Mar 21;47(11):3043-56. doi: 10.1039/c0cc04867d.
Brønsted acid catalysis has emerged as a new class of catalysis in modern organic synthesis. However, in order to make the utility of the Brønsted acid catalysis as broad as the well-developed Lewis acid catalysis, it is desirable to develop Brønsted acids demonstrating both high reactivities and selectivities. In this feature article, we will present our achievement in the design and development of strong Brønsted acids and their application to organic reactions. Furthermore, we will describe the Tf(2)NH-catalyzed Mukaiyama aldol reaction of super silyl enol ethers. We also will highlight the differences in reactivity and chemo- and stereo-selectivity between Brønsted and Lewis acid catalysis.
2. Chemistry of Fluorinated Carbon Acids: Synthesis, Physicochemical Properties, and Catalysis
Hikaru Yanai Chem Pharm Bull (Tokyo) . 2015;63(9):649-62. doi: 10.1248/cpb.c15-00487.
The bis[(trifluoromethyl)sulfonyl]methyl (Tf2CH; Tf=SO2CF3) group is known to be one of the strongest carbon acid functionalities. The acidity of such carbon acids in the gas phase is stronger than that of sulfuric acid. Our recent investigations have demonstrated that this type of carbon acids work as novel acid catalysts. In this paper, recent achievements in carbon acid chemistry by our research group, including synthesis, physicochemical properties, and catalysis, are summarized.
3. Boronic acid compounds as potential pharmaceutical agents
Binghe Wang, Xingming Gao, Wenqian Yang Med Res Rev . 2003 May;23(3):346-68. doi: 10.1002/med.10043.
Boronic acid compounds have been used, because of their unique structural features, for the development of potent enzyme inhibitors, boron neutron capture agents for cancer therapy, and as antibody mimics that recognize biologically important saccharides. Consequently, there has been a surge of interests in boronic acid compounds. This study reviews the recent development in this area during the last six years.
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