9797. Tryptophan

Nomenclature

CAS number: 73-22-3
l-Tryptophan; Trp; W; (S)-α-amino-1H-indole-3-propanoic acid; l-α-aminoindole-3-propionic acid; l-α-amino-3-indolepropionic acid; 2-amino-3-indolylpropanoic acid; l-β-3-indolylalanine; Ardeytropin (Ardeypharm); Kalma (Fresenius); Optimax (Merck KGaA); Pacitron (Rorer); Sedanoct (Woelm); Trofan (Upsher-Smith); Tryptan (Valeant).
C11H12N2O2; mol wt 204.23.
C 64.69%, H 5.92%, N 13.72%, O 15.67%.

Description and references

An essential amino acid for human development; precursor of serotonin, q.v. Isoln from casein: F. G. Hopkins, S. W. Cole, J. Physiol. 27, 418 (1902). Structure: A. Ellinger, Ber. 39, 2515 (1906); A. Ellinger, A. C. Flamand, Ber. 40, 3029 (1907). Early chemistry and biochemistry: Amino Acids and Proteins, D. M. Greenberg, Ed. (Charles C. Thomas, Springfield, IL, 1951) 950 pp., passim; J. P. Greenstein, M. Winitz, Chemistry of the Amino Acids vols 1-3 (John Wiley and Sons, Inc., New York, 1961) pp. 2316-2347, passim. Intrinsic fluorescent/phosphorescent moiety in proteins; used in characterizing structure and conformational changes: E. A. Burstein et al., Photochem. Photobiol. 18, 263 (1973); C. Pokalsky et al., J. Biol. Chem. 270, 3809 (1995); review of phosphorescence: S. Papp, J. M. Vanderkooi, Photochem. Photobiol. 49, 775-784 (1989). Review of microbial production: T. K. Maiti, S. P. Chatterjee, Hind. Antibiot. Bull. 33, 26-61 (1991). Review of biosynthesis: I. P. Crawford, G. V. Stauffer, Annu. Rev. Biochem. 49, 163-195 (1980); of nutrition and metabolism: J. C. Peters. Adv. Exp. Med. Biol. 294, 345-358 (1991). Review of use in depression: S. N. Young, J. Psychiatry Neurosci. 16, 241-246 (1991); in neuropsychiatric disorders: R. Sandyk, Int. J. Neurosci. 67, 127-144 (1992). Review as toxic agent in eosinophilia-myalgia syndrome (EMS): D. S. Milburn, C. W. Myers, DICP Ann. Pharmacother. 25, 1259 (1991); L. D. Kaufman, R. M. Philen, Drug Saf. 8, 89-98 (1993).

Chemical structure

Properties

Leaflets or plates from dil alc, dec 289° (rapid heating). [α]D23 -31.5° (c = 1); [α]D20 +2.4° (0.5N HCl); [α]D20 +0.15° (c = 2.43 in 0.5N NaOH). pK1 2.38; pK2 9.39. Soly in water (g/l): 8.23 at 0°; 10.57 at 20°; 11.36 at 25°; 17.06 at 50°; 27.95 at 75°; 49.87 at 100°. Sol in hot alcohol, in alkali hydroxides. Insol in chloroform.

Derivative

Hydrochloride.
C11H12N2O2.HCl; mol wt 240.69.
C 54.89%, H 5.44%, N 11.64%, O 13.29%, Cl 14.73%.

Properties

Needles from methanol, dec 251°.

Use

Probe for studying protein structure and dynamics.

Therapeutic Category

In treatment of depression, schizophrenia and other neuropsychiatric disorders.

Keywords

Antidepressant