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肉豆蔻酰 - 碳环(脱硫)辅酶A和S -(3 - 氧代十六烷基)辅酶A的合成,这两种都是肉豆蔻酰辅酶A:蛋白质N - 肉豆蔻酰转移酶的有效抑制剂。

Synthesis of myristoyl-carba(dethia)-coenzyme A and S-(3-oxohexadecyl)-coenzyme A, two potent inhibitors of myristoyl-CoA:protein N-myristoyltransferase.

作者信息

Wagner A P, Rétey J

机构信息

Department of Biochemistry, University of Karlsruhe, Federal Republic of Germany.

出版信息

Eur J Biochem. 1991 Feb 14;195(3):699-705. doi: 10.1111/j.1432-1033.1991.tb15756.x.

DOI:10.1111/j.1432-1033.1991.tb15756.x
PMID:1999191
Abstract
  1. Two non-hydrolysable analogues of myristoyl-coenzyme A were synthesised and spectroscopically characterized. Myristoyl-carba(dethia)coenzyme A was prepared in a multistep synthesis starting from tridecyl vinyl ketone. S-(3-Oxohexadecyl)-coenzyme A was synthesised from 3-oxohexadecyl chloride by direct condensation with coenzyme A. 2. Both analogues were strong competitive inhibitors of N-myristoyltransferase from yeast. Ki values of 0.3 and 0.25 microM were determined for myristoyl-carba(dethia)-coenzyme A and S-(3-oxohexadecyl)-coenzyme A, respectively.
摘要
  1. 合成了肉豆蔻酰辅酶A的两种不可水解类似物,并通过光谱进行了表征。肉豆蔻酰-碳硼(脱硫)辅酶A是从十三烷基乙烯基酮开始,经过多步合成制备的。S-(3-氧代十六烷基)-辅酶A是由3-氧代十六烷基氯与辅酶A直接缩合合成的。2. 这两种类似物都是酵母N-肉豆蔻酰转移酶的强竞争性抑制剂。肉豆蔻酰-碳硼(脱硫)-辅酶A和S-(3-氧代十六烷基)-辅酶A的Ki值分别测定为0.3和0.25微摩尔。

相似文献

1
Synthesis of myristoyl-carba(dethia)-coenzyme A and S-(3-oxohexadecyl)-coenzyme A, two potent inhibitors of myristoyl-CoA:protein N-myristoyltransferase.肉豆蔻酰 - 碳环(脱硫)辅酶A和S -(3 - 氧代十六烷基)辅酶A的合成,这两种都是肉豆蔻酰辅酶A:蛋白质N - 肉豆蔻酰转移酶的有效抑制剂。
Eur J Biochem. 1991 Feb 14;195(3):699-705. doi: 10.1111/j.1432-1033.1991.tb15756.x.
2
Synthesis of myristoyl CoA analogues and myristoyl peptides as inhibitors of myristoyl CoA:protein N-myristoyltransferase.肉豆蔻酰辅酶A类似物和肉豆蔻酰肽作为肉豆蔻酰辅酶A:蛋白质N-肉豆蔻酰转移酶抑制剂的合成
J Pharm Sci. 1994 Feb;83(2):233-8. doi: 10.1002/jps.2600830224.
3
Synthesis and characterization of inhibitors of myristoyl-CoA:protein N-myristoyltransferase.肉豆蔻酰辅酶A:蛋白质N-肉豆蔻酰转移酶抑制剂的合成与表征
Biochem Pharmacol. 1991;41(6-7):1067-74. doi: 10.1016/0006-2952(91)90215-q.
4
S-(2-oxopentadecyl)-CoA, a nonhydrolyzable analogue of myristoyl-CoA, is a potent inhibitor of myristoyl-CoA:protein N-myristoyltransferase.S-(2-氧代十五烷基)-辅酶A,一种肉豆蔻酰辅酶A的不可水解类似物,是肉豆蔻酰辅酶A:蛋白质N-肉豆蔻酰转移酶的有效抑制剂。
J Med Chem. 1989 Aug;32(8):1665-7. doi: 10.1021/jm00128a001.
5
Metabolic activation of 2-substituted derivatives of myristic acid to form potent inhibitors of myristoyl CoA:protein N-myristoyltransferase.肉豆蔻酸2-取代衍生物的代谢活化以形成肉豆蔻酰辅酶A:蛋白质N-肉豆蔻酰转移酶的强效抑制剂。
Biochemistry. 1990 Nov 20;29(46):10566-73. doi: 10.1021/bi00498a021.
6
The substrate specificity of Saccharomyces cerevisiae myristoyl-CoA: protein N-myristoyltransferase. Polar probes of the enzyme's myristoyl-CoA recognition site.酿酒酵母肉豆蔻酰辅酶A:蛋白质N-肉豆蔻酰转移酶的底物特异性。该酶肉豆蔻酰辅酶A识别位点的极性探针。
J Biol Chem. 1994 Feb 18;269(7):5346-57.
7
A highly convergent synthesis of myristoyl-carba(dethia)-coenzyme A.肉豆蔻酰基碳环(去硫)辅酶A的高效汇聚合成。
European J Org Chem. 2010 Mar;2010(9):1728-1735. doi: 10.1002/ejoc.200901410.
8
A comparative analysis of the kinetic mechanism and peptide substrate specificity of human and Saccharomyces cerevisiae myristoyl-CoA:protein N-myristoyltransferase.人源和酿酒酵母肉豆蔻酰辅酶A:蛋白质N-肉豆蔻酰转移酶的动力学机制及肽底物特异性的比较分析
J Biol Chem. 1993 May 15;268(14):9964-71.
9
Biochemical studies of Saccharomyces cerevisiae myristoyl-coenzyme A:protein N-myristoyltransferase mutants.酿酒酵母肉豆蔻酰辅酶A:蛋白质N-肉豆蔻酰转移酶突变体的生化研究
J Biol Chem. 1996 Dec 20;271(51):33131-40. doi: 10.1074/jbc.271.51.33131.
10
Isothermal titration calorimetric studies of Saccharomyces cerevisiae myristoyl-CoA:protein N-myristoyltransferase. Determinants of binding energy and catalytic discrimination among acyl-CoA and peptide ligands.酿酒酵母肉豆蔻酰辅酶A:蛋白质N-肉豆蔻酰转移酶的等温滴定量热研究。酰基辅酶A和肽配体之间结合能和催化识别的决定因素。
J Biol Chem. 1994 Apr 15;269(15):11045-53.

引用本文的文献

1
A highly convergent synthesis of myristoyl-carba(dethia)-coenzyme A.肉豆蔻酰基碳环(去硫)辅酶A的高效汇聚合成。
European J Org Chem. 2010 Mar;2010(9):1728-1735. doi: 10.1002/ejoc.200901410.