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| | L-CANALINE BASE Basic information |
| Product Name: | L-CANALINE BASE | | Synonyms: | L-CANALINE BASE;canaline;O-AMINO-L-HOMOSERINE;Canalin;L-Canalin;2-Amino-4-(aminooxy)butyric acid;(2S)-2-amino-4-aminooxybutanoic acid;(2S)-2-amino-4-aminooxy-butyric acid | | CAS: | 496-93-5 | | MF: | C4H10N2O3 | | MW: | 134.13 | | EINECS: | | | Product Categories: | Amino Acids | | Mol File: | 496-93-5.mol |  |
| | L-CANALINE BASE Chemical Properties |
| density | 1.298 | | storage temp. | 2-8°C | | solubility | ≤1mg/ml in DMSO | | form | crystalline solid | | pka | pK1: 2.40;pK2: 3.70;pK3: 9.20 (25°C) |
| | L-CANALINE BASE Usage And Synthesis |
| Description | L-Canaline is an aminooxy analog of ornithine that irreversibly inhibits aminotransferases (transaminases), including ornithine aminotransferase (Ki = 2 μM). It forms oximes with α-keto acids and aldehydes, most notably with pyridoxal phosphate, an essential cofactor of aminotransferases. L-Canaline is naturally found in plants, including legumes, and is involved in the metabolism of L-canavanine, an aminooxy analog of arginine. It is cytotoxic to a range of organisms, including bacteria, insects, and parasites. | | Definition | ChEBI: L-canaline is a non-proteinogenic L-alpha-amino acid that is L-homoserine in which the hydroxy group at position 4 is substituted by an aminooxy group. It has been isolated from legumes and plays an essential role in lugume chemical defense against insects. It has a role as a plant metabolite, an antineoplastic agent, an antimetabolite and a phytogenic insecticide. It is functionally related to a L-homoserine. It is a tautomer of a L-canaline zwitterion. | | Synthesis Reference(s) | Tetrahedron, 23, p. 4441, 1967 DOI: 10.1016/S0040-4020(01)88842-6 | | in vitro | canaline strongly inhibited the activity of pyridoxal-dependent enzymes, including amino acid decarboxylases, 5-hydroxytryptophan decarboxylase, aminotransferases, tyrosine aminotransferase, ornithine transcarbamylase and plasma diamino-oxidase. the canaline inhibition was due to complex formation between canaline and the pyridoxal coenzyme. l-canaline is one of the most potent inhibitors of pyridoxal enzymes. the ic50 value of l-canaline against ornithine aminotransferase was 3 ×10-6m [4]. | | in vivo | intraperitoneal administration of 500 mg of dl-canaline/kg body wt. only produced a transient inhibition of oat in brain and liver by 65-70%, suggesting that dl-canaline was not a useful tool in studies of biological consequences of oat inhibition. [1]. | | references | [1] bolkenius f n, kndgen b, seiler n. dl-canaline and 5-fluoromethylornithine. comparison of two inactivators of ornithine aminotransferase[j]. biochemical journal, 1990, 268(2): 409-414.
[2] rosenthal g a, rhodes d. l-canavanine transport and utilization in developing jack bean, canavalia ensiformis (l.) dc.[leguminosae][j]. plant physiology, 1984, 76(2): 541-544.
[3] peraino c, bunville l g, tahmisian t n. chemical, physical, and morphological properties of ornithine aminotransferase from rat liver[j]. journal of biological chemistry, 1969, 244(9): 2241-2249.
[4] rahiala e l, kekomki m, jnne j, et al. inhibition of pyridoxal enzymes by l-canaline[j]. biochimica et biophysica acta (bba)-enzymology, 1971, 227(2): 337-343. |
| | L-CANALINE BASE Preparation Products And Raw materials |
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