Title: Thymidine
CAS Registry Number: 50-89-5
Additional Names: 1-(2-Deoxy-b-D-ribofuranosyl)-5-methyluracil; thymine-2-desoxyriboside
Molecular Formula: C10H14N2O5
Molecular Weight: 242.23
Percent Composition: C 49.58%, H 5.83%, N 11.56%, O 33.03%
Literature References: Constituent of deoxyribonucleic acid, q.v. Isoln from thymonucleic acid: Levene, London, J. Biol. Chem. 83, 793 (1929). Structure: Levene, Tipson, ibid. 109, 623 (1935). Conformation: Lemieux, Can. J. Chem. 39, 116 (1961); Tollin et al., Nature 217, 1148 (1968). Prepn of thymidine-3¢-phosphate and of thymidine-5¢-phosphate: Tener, J. Am. Chem. Soc. 83, 165 (1961). Review: Basic Principles in Nucleic Acid Chemistry vol. 1, P. O. P. Ts'o, Ed. (Academic Press, New York, 1974) passim.
Properties: Rosettes of needles from ethyl acetate. mp 185°. Yields a sublimate of thymine when heated. [a]D25 +30.6° (c = 1.029). uv max (pH 7.2): 206.5, 267 nm (e ´ 10+3 9.8, 9.7). Absorption spectra: D. Voet et al., Biopolymers 1, 193 (1963). Sol in water, methanol, hot alcohol, hot acetone, hot ethyl acetate, pyridine, glacial acetic acid; sparingly sol in hot chloroform.
Melting point: mp 185°
Optical Rotation: [a]D25 +30.6° (c = 1.029)
Absorption maximum: uv max (pH 7.2): 206.5, 267 nm (e ´ 10+3 9.8, 9.7)
Derivative Type: Monotrityl thymidine
Molecular Formula: C29H28N2O5
Molecular Weight: 484.54
Percent Composition: C 71.88%, H 5.82%, N 5.78%, O 16.51%
Properties: Prepd by the action of triphenylmethyl chloride on thymidine in pyridine. mp 125°. [a]D24 +11.4° (c = 1.01 in acetone).
Melting point: mp 125°
Optical Rotation: [a]D24 +11.4° (c = 1.01 in acetone)
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