Inhibition of tyrosine phenol-lyase from Citrobacter freundii by 2-azatyrosine and 3-azatyrosine.
Inhibition of tyrosine phenol-lyase from Citrobacter freundii by 2-azatyrosine and 3-azatyrosine.
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2-氮杂酪氨酸和 3-氮杂酪氨酸对弗氏柠檬酸杆菌酪氨酸酚裂解酶的抑制作用。
DOI：
10.1021/bi015707s
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发表时间：
2001
期刊：
影响因子：
2.9
通讯作者：
Phillips Rs
中科院分区：
文献类型：
--
作者：
Watkins Eb;Phillips Rs
研究了2-氮杂酪氨酸和3-氮杂酪氨酸与弗氏柠檬酸杆菌酪氨酸酚裂解酶（TPL）的相互作用。通过氨基酸合成的标准方法合成2-氮杂-dl-酪氨酸和3-氮杂-dl-酪氨酸，而L-异构体分别用TPL（Watkins，E. B.，和菲利普斯，R. S.等人（2001）Bioorg.医学化学快报11，2099 - 2100）。3-研究了氮杂酪氨酸作为TPL的潜在过渡态类似物抑制剂。发现这两种化合物都是TPL的竞争性抑制剂，3-和2-氮杂-1-酪氨酸的Ki值分别为3.4 mM和135 μM。因此，3-氮杂酪氨酸不充当过渡态类似物，可能是由于在C-1处缺乏四面体几何形状。然而，2-氮杂-1-酪氨酸是迄今为止发现的TPL的最有效的竞争性抑制剂。2-氮杂-1-酪氨酸的Ki值是2-氮杂-dl-酪氨酸的一半，表明d-对映体作为抑制剂是无活性的。两种氮杂酪氨酸异构体都不是...
The interactions of 2-azatyrosine and 3-azatyrosine with tyrosine phenol-lyase (TPL) from Citrobacter freundii have been examined. 2-Aza-dl-tyrosine and 3-aza-dl-tyrosine were synthesized by standard methods of amino acid synthesis, while the l-isomers were prepared from 3-hydroxypyridine and 2-hydroxypyridine, respectively, with TPL (Watkins, E. B., and Phillips, R. S. (2001) Bioorg. Med. Chem. Lett. 11, 2099−2100). 3-Azatyrosine was examined as a potential transition state analogue inhibitor of TPL. Both compounds were found to be competitive inhibitors of TPL, with Ki values of 3.4 mM and 135 μM for 3- and 2-aza-l-tyrosine, respectively. Thus, 3-azatyrosine does not act as a transition state analogue, possibly due to the lack of tetrahedral geometry at C-1. However, 2-aza-l-tyrosine is the most potent competitive inhibitor of TPL found to date. The Ki value of 2-aza-l-tyrosine is half that of 2-aza-dl-tyrosine, indicating that the d-enantiomer is inactive as an inhibitor. Neither azatyrosine isomer was...