5328. Kynurenine
Nomenclature
CAS number: 343-65-7
α,2-Diamino-γ-oxobenzenebutanoic acid; 3-anthraniloylalanine. C10H12N2O3; mol wt 208.21.
C 57.69%, H 5.81%, N 13.45%, O 23.05%.
Description and references
An amino acid produced in the body from tryptophan. Isoln from urine of rabbits that had been fed tryptophan: Matsuoka, Yoshimatsu, Z. Physiol. Chem. 143, 206 (1925); Butenandt et al., ibid. 279, 27 (1943); Heidelberger et al., J. Biol. Chem. 179, 143 (1949). Structure and synthesis: Butenandt et al., loc. cit. Laboratory prepn by oxidation of l-tryptophan with a Pseudomonas sp.: Hayaishi, Meister, Biochem. Prep. 3, 108 (1953). From acetyltryptophan: Warnell, Berg, J. Am. Chem. Soc. 76, 1708 (1954); Auerbach, Knox, Methods Enzymol. 3, 620 (1957).
Derivative
l-Kynurenine hydrate.3C10H12N2O3.H2O; mol wt 642.66.
C 56.07%, H 5.96%, N 13.08%, O 24.90%.
Properties
Leaflets from water, dec 180-190°. [α]D20 29° (c = 0.4). Slightly sol in water (more sol than the dl-form). Forms a molecular compound with sucrose, C22H34N2O14.H2O, rosettes; dec 145-153°, [α]D21 +14.5° (c = 0.7). Soluble in water.Derivative
l-Kynurenine sulfate monohydrate.C10H12N2O3.H2SO4.H2O; mol wt 324.31.
C 37.03%, H 4.97%, N 8.64%, O 39.47%, S 9.89%.
Properties
Needles from water + alcohol. Darkens at 165°, dec 195°. [α]D20 +7.3° (c = 1). uv max (pH 7.0): 230, 257, 360 nm (ε 18,900, 7500, 4500). Soluble in water, slightly in alcohol. Kynurenine sulfate requires 3 molecules alkali for neutralization in alcoholic soln.Derivative
l-Kynurenine diacetate.C14H16N2O5; mol wt 292.29.
C 57.53%, H 5.52%, N 9.58%, O 27.37%.
Properties
Obtained by acetylating l-kynurenine with ketene. Needles, mp 198°.Derivative
Anhydro-l-kynurenine monoacetate.C12H12N2O3; mol wt 232.24.
C 62.06%, H 5.21%, N 12.06%, O 20.67%.
Properties
Obtained by acetylating l-kynurenine with acetic anhydride in pyridine. Needles from alc, darkens at 215°, dec 237°.Derivative
dl-Kynurenine sulfate.C10H12N2O3.H2SO4; mol wt 306.29.
C 39.21%, H 4.61%, N 9.15%, O 36.57%, S 10.47%.