对甲酚甲基羟化酶催化4-乙基苯酚羟基化生成的1-(4'-羟基苯基)乙醇的立体化学
Stereochemistry of 1-(4'-hydroxyphenyl)ethanol produced by hydroxylation of 4-ethylphenol by p-cresol methylhydroxylase.
作者信息
McIntire W, Hopper D J, Craig J C, Everhart E T, Webster R V, Causer M J, Singer T P
出版信息
Biochem J. 1984 Dec 1;224(2):617-21. doi: 10.1042/bj2240617.
Abstract
Enzymic hydroxylation of 4-ethylphenol by (a) Pseudomonas putida and (b) highly purified p-cresol methylhydroxylase gave optically active 1-(4'-hydroxyphenyl)-ethanol. The products were transformed into the phenolic methyl ethers and shown to contain 69.5% and 65.6%, respectively, of the (S)-(-)-isomer. The stereochemistry of the reaction is discussed in terms of three distinct steps occurring at the active site of the enzyme.
摘要
（a）恶臭假单胞菌和（b）高度纯化的对甲酚甲基羟化酶对4-乙基苯酚进行酶促羟基化反应，生成旋光性的1-（4'-羟基苯基）乙醇。产物被转化为酚类甲基醚，结果显示分别含有69.5%和65.6%的（S）-（-）-异构体。根据在酶活性位点发生的三个不同步骤讨论了该反应的立体化学。
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本文引用的文献
1
An instance of partially asymmetric enzymatic synthesis.部分不对称酶促合成的一个实例。
Biochim Biophys Acta. 1952 Jan;8(1):108-9. doi: 10.1016/0006-3002(52)90015-2.
2
8 alpha-(O-Tyrosyl)flavin adenine dinucleotide, the prosthetic group of bacterial p-cresol methylhydroxylase.8α-（O-酪氨酰）黄素腺嘌呤二核苷酸，细菌对甲酚甲基羟化酶的辅基。
Biochemistry. 1981 May 26;20(11):3068-75. doi: 10.1021/bi00514a013.
3
Stereochemical outcome of processing of fluorinated substrates by ATP citrate lyase and malate synthase.柠檬酸-ATP裂解酶和苹果酸合酶对氟化底物加工的立体化学结果。
Biochemistry. 1981 Jun 23;20(13):3719-23. doi: 10.1021/bi00516a008.
4
The specificities and configurations of ternary complexes of yeast and liver alcohol dehydrogenases.酵母和肝脏乙醇脱氢酶三元复合物的特异性及构型
Biochem J. 1967 Jul;104(1):165-72. doi: 10.1042/bj1040165.
5
P-cresol and 3,5-xylenol methylhydroxylases in Pseudomonas putida N.C.I.B. 9896.恶臭假单胞菌N.C.I.B. 9896中的对甲酚和3,5-二甲苯酚甲基羟化酶
Biochem J. 1978 Nov 1;175(2):649-58. doi: 10.1042/bj1750649.
6
Incorporation of [18O]water in the formation of p-hydroxybenzyl alcohol by the p-cresol methylhydroxylase from Pseudomonas putida.恶臭假单胞菌的对甲酚甲基羟化酶利用[18O]水参与对羟基苯甲醇形成的过程。
Biochem J. 1978 Oct 1;175(1):345-7. doi: 10.1042/bj1750345.
7
Enantiomeric specificity of glyceraldehyde 3-phosphate dehydrogenase.3-磷酸甘油醛脱氢酶的对映体特异性
Arch Biochem Biophys. 1978 Mar;186(2):335-42. doi: 10.1016/0003-9861(78)90443-5.
8
The purification and properties of p-cresol-(acceptor) oxidoreductase (hydroxylating), a flavocytochrome from Pseudomonas putida.来自恶臭假单胞菌的对甲酚-（受体）氧化还原酶（羟化）（一种黄素细胞色素）的纯化及性质
Biochem J. 1977 Oct 1;167(1):155-62. doi: 10.1042/bj1670155.
9
Investigation of the mechanism of the methylmalonyl-CoA mutase reaction with the substrate analogue: ethylmalonyl-CoA.利用底物类似物：乙基丙二酰辅酶A对甲基丙二酰辅酶A变位酶反应机制的研究。
Eur J Biochem. 1978 Feb;83(2):437-51. doi: 10.1111/j.1432-1033.1978.tb12110.x.
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