9839. Tyrosine

Nomenclature

CAS number: 60-18-4
l-Tyrosine; Tyr; Y; β-(p-hydroxyphenyl)alanine; α-amino-p-hydroxyhydrocinnamic acid; (S)-α-amino-4-hydroxybenzenepropanoic acid.
C9H11NO3; mol wt 181.19.
C 59.66%, H 6.12%, N 7.73%, O 26.49%.

Description and references

Non-essential amino acid for human development; precursor for the synthesis of thyroid hormones and select neurotransmitters, such as dopamine and norepinephrine. May be considered essential by the brain. Name derived from the Greek “tyros” for “cheese” from which it was first identified and isolated: J. Liebig, Ann. 57, 127 (1846); idem, ibid. 62, 257 (1847). 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 vol 1-3 (John Wiley and Sons, Inc., New York, 1961) pp. 2348-2367, passim. Synthesis of labeled form: Y. Watanabe et al., Acta Radiol. 376 (Suppl.), 110 (1991). Intrinsic fluorophore in proteins; used in characterizing structure and conformational changes: V. Giancotti et al., Biochim. Biophys. Acta 624, 60 (1980); S. T. Ferreira et al., Biophys. J. 66, 1185 (1994); B. Kierdaszuk et al., Photochem. Photobiol. 61, 319 (1995). Review of determn in blood: E. Robins, Methods Biochem. Anal. 17, 287-309 (1969). Review of neurotransmitter synthesis: C. J. Gibson, Retina 2, 332-340 (1982). Review of toxicity: C. Laberge et al., Adv. Exp. Med. Biol. 206, 209-221 (1986). Review of post-translational phosphorylation: S. Atherton-Fessler et al., Semin. Cell Biol. 4, 433-442 (1993); sulfation: C. Niehrs et al., Chem. Biol. Interact. 92, 257-271 (1994).

Chemical structure

Properties

Fine silky needles, dec 342-344° (closed capillary, bath preheated to 280°, rapid heating). d 1.456. pK1 2.20; pK2 9.11; pK3 10.07. [α]D22 10.6° (c = 4 in HCl); [α]D18 13.2° (c = 4 in 3N NaOH). Soly in water (g/100 g): 0.02 at 0°; 0.045 at 25°; 0.105 at 50°; 0.244 at 75°; 0.565 at 100°. Insol in common neutral solvents, such as abs alcohol, ether, acetone, except water. Sol in alkaline solns.

Derivative

dl-Form.

Properties

Synthetic product. Stout needles. Dec 316°. Soly in water (g/100 g): 0.0147 at 0°; 0.351 at 25°; 0.0836 at 50°.

Derivative

d-Form.

Properties

Crystals. Dec 310-314°. [α]D25 +10.3° (c = 4 in HCl). Soly in water (g/100 g): 0.196 at 0°; 0.1052 at 50°.

Use

Probe for studying protein structure and dynamics.