以腺苷5'-[γ(S)-16O,17O,18O]三磷酸为底物时酵母己糖激酶催化的磷酰基转移的立体化学过程。
The stereochemical course of yeast hexokinase-catalysed phosphoryl transfer by using adenosine 5'[gamma(S)-16O,17O,18O]triphosphate as substrate.
作者信息
Lowe G, Potter B V
出版信息
Biochem J. 1981 Oct 1;199(1):227-33. doi: 10.1042/bj1990227.
Abstract
Adenosine 5'[gamma(S)-16O, 17O, 18O]triphosphate has been synthesized and used to determine the stereochemical course of phosphoryl transfer catalysed by yeast hexokinase. The chirality at phosphorus of the D-glucose 6-[16O,17O,18O]phosphate formed was analysed, after cyclization and methylation, by 31P n.m.r. spectroscopy. The phosphoryl transfer was found to occur with inversion of configuration, with a stereoselectivity in excess of 94%. The simplest interpretation of this result is that the phosphoryl group is transferred between substrates in the enzyme-substrate ternary complex by an 'in line' mechanism.
摘要
5'-[γ(S)-16O, 17O, 18O]三磷酸腺苷已被合成，并用于确定酵母己糖激酶催化的磷酰基转移的立体化学过程。在环化和甲基化后，通过31P核磁共振光谱分析了形成的D-葡萄糖6-[16O,17O,18O]磷酸酯磷原子处的手性。发现磷酰基转移以构型翻转的方式发生，立体选择性超过94%。对该结果最简单的解释是，磷酰基通过“直线”机制在酶-底物三元复合物中的底物之间转移。
相似文献
1
The stereochemical course of yeast hexokinase-catalysed phosphoryl transfer by using adenosine 5'[gamma(S)-16O,17O,18O]triphosphate as substrate.以腺苷5'-[γ(S)-16O,17O,18O]三磷酸为底物时酵母己糖激酶催化的磷酰基转移的立体化学过程。
Biochem J. 1981 Oct 1;199(1):227-33. doi: 10.1042/bj1990227.
2
The stereochemical course of phosphoryl transfer catalysed by glucokinase.葡萄糖激酶催化的磷酰基转移的立体化学过程。
Biochem J. 1982 Feb 1;201(2):421-3. doi: 10.1042/bj2010421.
3
The stereochemical course of phosphoryl transfer catalysed by Bacillus stearothermophilus and rabbit skeletal-muscle phosphofructokinase with a chiral [16O,17O,18O]phosphate ester.嗜热脂肪芽孢杆菌和兔骨骼肌磷酸果糖激酶催化的手性[16O,17O,18O]磷酸酯磷酰基转移的立体化学过程。
Biochem J. 1981 Nov 1;199(2):427-32. doi: 10.1042/bj1990427.
4
The stereochemical course of phosphoryl transfer catalysed by polynucleotide kinase (bacteriophage-T4-infected Escherichia coli B).多核苷酸激酶（噬菌体T4感染的大肠杆菌B）催化的磷酰基转移的立体化学过程。
Biochem J. 1981 Oct 1;199(1):273-6. doi: 10.1042/bj1990273.
5
A stereochemical investigation of phosphoryl transfer catalysed by phosphoglucomutase by the use of alpha-D-glucose 1-[(S)-16O,17O,18O]phosphate.通过使用α-D-葡萄糖1-[(S)-16O,17O,18O]磷酸对磷酸葡萄糖变位酶催化的磷酰基转移进行立体化学研究。
Biochem J. 1981 Dec 1;199(3):693-8. doi: 10.1042/bj1990693.
6
The stereochemical course of phosphoryl transfer catalyzed by herpes simplex virus type I-induced thymidine kinase.
J Biol Chem. 1986 Feb 15;261(5):1985-7.
7
Stereochemical course of phosphokinases. The use of adenosine [gamma-(S)-16O,17O,18O]triphosphate and the mechanistic consequences for the reactions catalyzed by glycerol kinase, hexokinase, pyruvate kinase, and acetate kinase.磷酸激酶的立体化学过程。腺苷[γ-(S)-16O,17O,18O]三磷酸的应用及其对甘油激酶、己糖激酶、丙酮酸激酶和乙酸激酶催化反应的机制影响。
Biochemistry. 1979 Sep 4;18(18):3927-33. doi: 10.1021/bi00585a013.
8
Stereochemical course of a phosphokinase using a chiral [18O]phosphorothioate. Comparison with the transfer of a chiral [16O,17O,18O]phosphoryl group.使用手性[18O]硫代磷酸酯的磷酸激酶的立体化学过程。与手性[16O,17O,18O]磷酰基转移的比较。
Biochemistry. 1980 Jan 22;19(2):325-9. doi: 10.1021/bi00543a012.
9
Stereochemistry of phosphoryl transfer.磷酰基转移的立体化学
Philos Trans R Soc Lond B Biol Sci. 1981 Jun 26;293(1063):75-92. doi: 10.1098/rstb.1981.0062.
10
The stereochemical course of the reaction catalyzed by creatine kinase.
J Biol Chem. 1981 Jun 25;256(12):5967-9.
引用本文的文献
1
UDP-GlcNAc 2-Epimerase/ManNAc Kinase (GNE): A Master Regulator of Sialic Acid Synthesis.UDP-N-乙酰葡糖胺2-差向异构酶/甘露糖胺激酶（GNE）：唾液酸合成的主要调节因子
Top Curr Chem. 2015;366:97-137. doi: 10.1007/128_2013_464.
2
Mechanism of liver glucokinase.肝脏葡萄糖激酶的机制。
Mol Cell Biochem. 1982 Apr 30;44(2):71-80. doi: 10.1007/BF00226892.
3
The stereochemical course of phosphoryl transfer catalysed by glucokinase.葡萄糖激酶催化的磷酰基转移的立体化学过程。
Biochem J. 1982 Feb 1;201(2):421-3. doi: 10.1042/bj2010421.
4
The stereochemical course of phosphoryl transfer catalysed by glucose 6-phosphatase.葡萄糖6-磷酸酶催化的磷酰基转移的立体化学过程。
Biochem J. 1982 Mar 1;201(3):665-8. doi: 10.1042/bj2010665.
5
The stereochemical course of hydrolysis catalysed by snake venom 5'-nucleotide phosphodiesterase.蛇毒5'-核苷酸磷酸二酯酶催化水解的立体化学过程。
Biochem J. 1981 Nov 1;199(2):447-51. doi: 10.1042/bj1990447.
6
The stereochemical course of phosphoryl transfer catalysed by polynucleotide kinase (bacteriophage-T4-infected Escherichia coli B).多核苷酸激酶（噬菌体T4感染的大肠杆菌B）催化的磷酰基转移的立体化学过程。
Biochem J. 1981 Oct 1;199(1):273-6. doi: 10.1042/bj1990273.
本文引用的文献
1
2
Crystallographic studies and model building of ATP at the active site of hexokinase.己糖激酶活性位点处ATP的晶体学研究与模型构建。
J Mol Biol. 1980 Jun 15;140(1):1-14. doi: 10.1016/0022-2836(80)90353-8.
3
Applicability of the phosphorus-31 (oxygen-17) nuclear magnetic resonance method in the study of enzyme mechanism involving phosphorus.磷-31（氧-17）核磁共振方法在涉及磷的酶机制研究中的适用性。
Biochemistry. 1980 Jul 22;19(15):3531-6. doi: 10.1021/bi00556a018.
4
Structure of a complex between yeast hexokinase A and glucose. II. Detailed comparisons of conformation and active site configuration with the native hexokinase B monomer and dimer.酵母己糖激酶A与葡萄糖复合物的结构。II. 与天然己糖激酶B单体和二聚体的构象和活性位点构型的详细比较。
J Mol Biol. 1980 Jun 25;140(2):211-30. doi: 10.1016/0022-2836(80)90103-5.
5
Structure of a complex between yeast hexokinase A and glucose. I. Structure determination and refinement at 3.5 A resolution.酵母己糖激酶A与葡萄糖复合物的结构。I. 3.5埃分辨率下的结构测定与精修
J Mol Biol. 1980 Jun 25;140(2):183-209. doi: 10.1016/0022-2836(80)90102-3.
6
Mechanism of phosphoryl transfer by hexokinase.
Biochem Biophys Res Commun. 1980 May 30;94(2):573-8. doi: 10.1016/0006-291x(80)91270-x.
7
Enzyme-catalyzed phosphoryl transfer reactions.酶催化的磷酰基转移反应。
Annu Rev Biochem. 1980;49:877-919. doi: 10.1146/annurev.bi.49.070180.004305.
8
Stereochemical course of a phosphokinase using a chiral [18O]phosphorothioate. Comparison with the transfer of a chiral [16O,17O,18O]phosphoryl group.使用手性[18O]硫代磷酸酯的磷酸激酶的立体化学过程。与手性[16O,17O,18O]磷酰基转移的比较。
Biochemistry. 1980 Jan 22;19(2):325-9. doi: 10.1021/bi00543a012.
9
The hexokinases: kinetic, physical, and regulatory properties.己糖激酶：动力学、物理及调节特性
Adv Enzymol Relat Areas Mol Biol. 1973;39:249-326. doi: 10.1002/9780470122846.ch4.
10
Thiophosphate-analogues and 1-N-oxides of ATP and ADP in mitochondrial translocation and phosphoryl-transfer reactions.
Eur J Biochem. 1973 Dec 17;40(2):485-91. doi: 10.1111/j.1432-1033.1973.tb03217.x.
Zotero 插件