A natural inhibitor of aminotransferases
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L-Canaline

Item No. 9002357

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
O-amino-L-homoserine
CAS Number
496-93-5
Molecular Formula
C4H10N2O3
Formula Weight
134.1
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: 1 mg/mlPBS (pH 7.2): 10 mg/ml
SMILES
N[C@@H](CCON)C(O)=O
InChi Code
InChI=1S/C4H10N2O3/c5-3(4(7)8)1-2-9-6/h3H,1-2,5-6H2,(H,7,8)/t3-/m0/s1
InChi Key
FQPGMQABJNQLLF-VKHMYHEASA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    1 mg

    $54

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    5 mg

    $238

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    10 mg

    $418

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    25 mg

    $913

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    Product Description

    L-Canaline is an aminooxy analog of ornithine that irreversibly inhibits aminotransferases (transaminases), including ornithine aminotransferase (Ki = 2 µM).1,2,3 It forms oximes with α-keto acids and aldehydes, most notably with pyridoxal phosphate, an essential cofactor of aminotransferases.3 L-Canaline is naturally found in plants, including legumes, and is involved in the metabolism of L-canavanine, an aminooxy analog of arginine.4 It is cytotoxic to a range of organisms, including bacteria, insects, and parasites.2,4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bolkenius, F.N., Knödgen, B., and Seiler, N. DL-Canaline and 5-fluoromethylornithine. Comparison of two inactivators of ornithine aminotransferase. Biochem. J. 268, 409-414 (1990).

    2. Heilbronn, J., Wilson, J., and Berger, B.J. Tyrosine aminotransferase catalyzes the final step of methionine recycling in Klebsiella pneumoniae. J. Bacteriol. 181(6), 1739-1747 (1999).

    3. Worthen, D.R., Ratliff, D.K., Rosenthal, G.A., et al. Structure-activity studies of L-canaline-mediated inhibition of porcinealanine aminotransferase. Chem. Res. Toxicol. 9(8), 1293-1297 (1996).

    4. Rosenthal, G.A. L-Canavanine Transport and Utilization in Developing Jack Bean, Canavalia ensiformis (L.) DC. [Leguminosae]. Plant Physiol. 69, 1066-1069 (1982).

    5. Berger, B.J. Antimalarial activities of aminooxy compounds. Antimicrob. Agents Chemother. 44(9), 2540-2542 (2000).