Uses
3-Bromo-L-tyrosine is used in the preparation and synthesis of polyclonal antibodies that work against brominated protein related allergic responses and afflictions. Also effective in asthma control a
nd prediction in children.
Definition
ChEBI: 3-bromo-L-tyrosine is a bromoamino acid comprising an L-tyrosine core with a bromo- substituent ortho to the hydroxy group on the benzene ring. It is a bromoamino acid, a L-tyrosine derivative, a member of bromobenzenes and a non-proteinogenic L-alpha-amino acid. It is a tautomer of a 3-bromo-L-tyrosine zwitterion.
Synthesis
The general procedure for the synthesis of (S)-2-amino-3-(3-bromo-4-hydroxyphenyl)propionic acid from L-tyrosine was as follows: reaction of D- or L-tyrosine (1.0 g) with N-bromosuccinimide (NBS, 1.5 g, 8.3 mmol) in anhydrous THF (15 mL). The reaction mixture was stirred overnight at room temperature. Upon completion of the reaction, the solution was concentrated under reduced pressure and purified by rapid column chromatography on silica gel to afford D- or L-3-bromotyrosine (100 mg). The product was analyzed by electrospray mass spectrometry (positive ion mode) and showed m/z 260/262 (1:1).1H NMR (500 MHz, CD3OD) data were as follows: δH 7.46 (s, H-2); 7.13 (d, J = 8.2 Hz, H-6); 6.91 (d, J = 8.2 Hz, H-5); 3.97 (m, H-8); 3.22 (dd, J = 4.6, 14.6 Hz, H-7a); 3.03 (dd, J = 7.8, 14.6 Hz, H-7b).
References
[1] Amino Acids, 2013, vol. 44, # 2, p. 529 - 532
[2] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1925, vol. 144, p. 250
[3] Patent: US2007/259883, 2007, A1. Location in patent: Page/Page column 8
