Title: Phenylalanine
CAS Registry Number: 63-91-2
CAS Name: L-Phenylalanine
Additional Names: Phe; F; b-phenylalanine; a-aminohydrocinnamic acid; (S)-2-amino-3-phenylpropanoic acid; a-amino-b-phenylpropionic acid
Molecular Formula: C9H11NO2
Molecular Weight: 165.19
Percent Composition: C 65.44%, H 6.71%, N 8.48%, O 19.37%
Literature References: Essential amino acid for human development. Originally isolated from the sprouts of lupine: E. Schulze, J. Barbieri, Ber. 12, 1924 (1879). 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. 2156-2177, passim. Synthesis from L-tyrosine: V. Viswanatha, V. J. Hruby, J. Org. Chem. 45, 2010 (1980). Colorimetric determn in blood: R. S. Campbell et al., Ann. Clin. Biochem. 31, 140 (1994). Effects on food intake: G. H. Anderson, L. A. Leiter, Appetite 11, Suppl. 48 (1988); P. J. Rogers, J. E. Blundell, Physiol. Behav. 56, 247 (1994). Clinical trial in vitiligo: C. Antoniou et al., Int. J. Dermatol. 28, 545 (1989); A. H. Siddiqui et al., Dermatology 188, 215 (1994). Review of metabolism: H. N. Munro, J. Toxicol. Environ. Health 2, 189-206 (1976). Review of role in phenylketonuria: S. P. Bessman, Nutr. Rev. 37, 209-220 (1979); F. Güttler, Acta Paediatr. Scand. 73, 705-716 (1984). Review of microbial production: T. K. Maiti, S. P. Chatterjee, Hind. Antibiot. Bull. 32, 3-26 (1990).
Properties: Monoclinic plates, leaflets from warm concd aq solns. Hydrated needles from dil solns. Dec 283°. Sublimes in vacuo. [a]D20 -35.1° (c = 1.94). pK1 1.83; pK2 9.13. Soly in water (g/l): 19.8 at 0°; 29.6 at 25°; 44.3 at 50°; 66.2 at 75°; 99.0 at 100°. Very slightly sol in methanol, ethanol.
pKa: pK1 1.83; pK2 9.13
Optical Rotation: [a]D20 -35.1° (c = 1.94)
Derivative Type: D-Form
CAS Registry Number: 673-06-3
Additional Names: (R)-Phenylalanine
Trademarks: Sabiden (Szabo)
Literature References: Occurs naturally in microbial products such as tyrocidine, q.v.: A. H. Gordon et al., Biochem. J. 37, 313 (1943). May be used as a source for L-form in man. Biotransformation: S. Tokuhisa et al., Chem. Pharm. Bull. 29, 514 (1981). Evaluation of D-form in multiple sclerosis: A. Winter, Neurol. Orthopaed. J. Med. Surg. 5, 39 (1984).
Properties: Leaflets from water, dec 285°. [a]D20 +35.0° (c = 2.04); [a]D20 +7.1° (c = 3.8 in 18% HCl). One gram dissolves in 35.5 ml water at 16°. Sparingly sol in methanol.
Optical Rotation: [a]D20 +35.0° (c = 2.04); [a]D20 +7.1° (c = 3.8 in 18% HCl)
Derivative Type: DL-Form
CAS Registry Number: 150-30-1
Properties: Monoclinic leaflets or prisms from water or alcohol, sweetish taste. Dec 271-273°. Sublimes in vacuo. pK1 2.58; pK2 9.24. Soly in water (g/l): 9.97 at 0°; 14.11 at 25°; 21.87 at 50°; 37.08 at 75°; 68.9 at 100°.
pKa: pK1 2.58; pK2 9.24
Use: Component of the artificial sweetner aspartame, q.v.; nutrient. |