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              sigmaL-天冬酰胺

              • 更新時(shí)間:  2023-07-24
              • 產(chǎn)品型號(hào):  A8381
              • 簡(jiǎn)單描述
              • sigmaL-天冬酰胺
                assay

                ≥99% (TLC)

                mp

                233-235 °C(lit.)
              詳細(xì)介紹

              sigmaL-天冬酰胺

              L-Asparagine monohydrate
              Product Number A 8381
              Store at Room Temperature
              Product Description
              Molecular Formula: C4H8N2O3 • H2O
              Molecular Weight: 150.1
              CAS Number: 5794-13-8
              pKa: 2.14 (-COOH), 8.72 (-NH2)1
              pI: 5.431
              Specific Rotation: +32.6°
              (10 mg/ml, 0.1 M HCl, 20 °C)
              Melting Point: 234-235 °C2
              Synonyms: (S)-2-aminosuccinic acid 4-amide,
              L-aspartic acid 4-amide, α-aminoauccinamic acid,
              aspartic acid β-amide2
              The amino acid L-asparagine is a structural analog of
              L-aspartic acid, where the side chain of the carboxylic
              acid moiety is amidated, to give a terminal amine
              group. This renders L-asparagine neutral at
              physiological pH. The amide group of asparagine is
              derived from glutamate, in the reaction of aspartate
              and glutamine in the presence of ATP to yield
              asparagine and glutamate.3 In vivo, asparagine is
              hydrolyzed to aspartate and NH4
              + by asparaginase.4
              Asparagine is also an important amino acid in
              glycopeptide bonds, via N-glycosyl linkages to the
              sugar rings.3
              L-Asparagine is used in cell culture media and is a
              component of MEM non-essential amino acids solution
              (Product No. M 7145). L-Asparagine has been shown
              to enhance ornithine decarboxylase activity in cultured
              human colon adenocarcinoma Caco-2 cells and in
              cultured IEC-6 intestinal epithelial cells.5,6 Spore
              germination in Bacillus subtilis has been increased in
              the presence of L-asparagine.7
              An isoxazoline RGD mimic plaet GPIIb/IIIa
              antagonist has been prepared by chiral synthesis with
              L-asparagine as a starting material.8 L-Asparagine
              has been utilized in the synthesis of 4-azalysine
              building blocks for application to combinatorial
              chemistry.9
              Precautions and Disclaimer
              For Laboratory Use Only. Not for drug, household or
              other uses.
              Preparation Instructions
              This product is soluble in water (50 mg/ml), with heat
              as needed, yielding a clear, colorless solution.
              References
              1. Molecular Biology Lab, Brown, T. A., ed., BIOS
              Scientific Publishers (Oxford, UK: 1991), p. 29.
              2. The Merck Index, 12th ed., Entry# 872.
              3. Textbook of Biochemistry with Clinical
              Correlations, 5th ed., Devlin, T. M., ed., Wiley-Liss
              (New York, NY: 2002), pp. 97, 680-681, 785-786.
              4. Biochemistry, 3rd ed., Stryer, L., W. H. Freeman
              (New York, NY: 1988), pp. 18, 504.
              5. Chabanon, H., et al., Increased translation
              efficiency and antizyme-dependent stabilization of
              ornithine decarboxylase in amino acidsupplemented
              human colon adenocarcinoma
              cells, Caco-2. Biochem. J., 348(Pt 2), 401-408
              (2000).
              6. Ray, R. M., et al., Interaction of asparagine and
              EGF in the regulation of ornithine decarboxylase in
              IEC-6 cells. Am. J. Physiol., 276(3 Pt 1), G773-
              780.
              7. Cabrera-Martinez, R. M., et al., Effects of
              overexpression of nutrient receptors on
              germination of spores of Bacillus subtilis. J.
              Bacteriol., 185(8), 2457-2464 (2003).
              8. Zhang L. H., et al., The Enantiospecific synthesis
              of an isoxazoline. A RGD mimic plaet GPIIb/IIIa
              antagonist. J. Org. Chem., 62(8), 2466-2470
              (1997).
              9. Chhabra, S. R., et al., Homochiral 4-azalysine
              building blocks: syntheses and applications in
              solid-phase chemistry. J. Org. Chem., 67(12),
              4017-4029 (2002).
              GCY/RXR 8/03
              Sigma brand

               


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