Canavanine
Title: Canavanine
CAS Registry Number: 543-38-4
CAS Name: O-[(Aminoiminomethyl)amino]homoserine
Additional Names: 2-amino-4-(guanidinooxy)butyric acid
Molecular Formula: C5H12N4O3
Molecular Weight: 176.17
Percent Composition: C 34.09%, H 6.87%, N 31.80%, O 27.25%
Line Formula: H2NC(NH)NHOCH2CH2CH(NH2)COOH
Literature References: Basic amino acid isolated as L-canavanine from jack beans, Canavalia ensiformis (L.) DC., Leguminosae: Kitagawa, Tomiyama, J. Biochem. (Tokyo) 11, 265 (1929). Constitutes about 1.5% of the dry weight of alfalfa seeds and sprouts: E. A. Bell Biochem. J. 75, 618 (1960). Distribution in the plant kingdom: Turner, Harborne, Phytochemistry 6, 863 (1967). Structure: Gulland, Morris, J. Chem. Soc. 1935, 763; Kitagawa, Takani, J. Biochem. (Tokyo) 23, 181 (1936). Configuration: Cadden, Proc. Soc. Exp. Biol. Med. 45, 224 (1940). Synthesis of racemate: Nyberg, Christensen, J. Am. Chem. Soc. 79, 1222 (1957); Frankel et al., J. Chem. Soc. 1963, 3127. Alternate synthesis: Yamada et al., Agric. Biol. Chem. 37, 2201 (1973). Bears resemblance to arginine, q.v. and is often used as substrate to some enzymes normally acting on arginine. Accordingly it is a potent growth inhibitor of many organisms: Pilcher et al., Proc. Soc. Exp. Biol. Med. 88, 79 (1955). Toxic to mammals: B. Tschiersch, Pharmazie 17, 621 (1962). L-Canavanine induces certain hematologic and serologic abnormalities characteristic of systemic lupus erythematosus in monkeys: M. R. Malinow et al., Science 216, 415 (1982).
Properties: Crystals from abs alcohol, mp 184°. [a]D20 +7.9° (c = 3.2).
Melting point: mp 184°
Optical Rotation: [a]D20 +7.9° (c = 3.2)
 
Derivative Type: Sulfate
Molecular Formula: C5H14N4O7S
Molecular Weight: 274.25
Percent Composition: C 21.90%, H 5.15%, N 20.43%, O 40.84%, S 11.69%
Properties: Crystals from dil alcohol, dec 172°. [a]D17 +19.4° (c = 2). Freely sol in water.
Optical Rotation: [a]D17 +19.4° (c = 2)
 
Derivative Type: DL-Form
Properties: Crystals from ethanol, mp 180-182°. Soluble in water. Practically insol in alcohol. Forms a monohydrochloride, mp 190°.
Melting point: mp 180-182°; mp 190°

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