McCord T J, Smith D R, Winters D W, Grimes J F, Hulme K L, Robinson L Q, Gage L D, Davis A L
J Med Chem. 1975 Jan;18(1):26-9. doi: 10.1021/jm00235a006.
2-Chlorotyrosine and 2-bromotyrosine, as well as the previously reported 2-fluorotyrosine, were synthesized by hydrolysis of the condensation products from the appropriate benzyl bromide and ethyl acetamidomalonate and were compared with the corresponding 3-halotyrosines as growth inhibitors of Escherichia coli 9723, Streptococcus faecalis 8043 and Lactobacillus plantarum 8014. In contrast to the 2- and 3-fluorotyrosines which were equally effective as growth inhibitors, the 2-chloro- and 2-bromotyrosines were much more effective than the 3-chloro- and 3-bromotyrosines in inhibiting the growth of the three microorganisms. For each of the assay organisms, the growth inhibitions of all three 2-halotyrosines were reversed competitively in varying degrees by tyrosine.
通过适当的苄基溴和乙酰氨基丙二酸乙酯的缩合产物水解合成了2-氯酪氨酸和2-溴酪氨酸，以及先前报道的2-氟酪氨酸，并将它们作为大肠杆菌9723、粪肠球菌8043和植物乳杆菌8014的生长抑制剂与相应的3-卤酪氨酸进行了比较。与同样有效作为生长抑制剂的2-和3-氟酪氨酸不同，2-氯酪氨酸和2-溴酪氨酸在抑制这三种微生物的生长方面比3-氯酪氨酸和3-溴酪氨酸有效得多。对于每种受试生物体，酪氨酸都能不同程度地竞争性逆转所有三种2-卤酪氨酸的生长抑制作用。
