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1
myo-Inositol phosphorothioates, phosphatase-resistant analogues of myo-inositol phosphates. Synthesis of DL-myo-inositol 1,4-bisphosphate and DL-myo-inositol 1,4-bisphosphorothioate.肌醇硫代磷酸酯，肌醇磷酸酯的抗磷酸酶类似物。DL-肌醇1,4-二磷酸酯和DL-肌醇1,4-二硫代磷酸酯的合成。
Biochem J. 1987 Sep 15;246(3):771-4. doi: 10.1042/bj2460771.
2
The preparation of intermediates for the synthesis of 1D-myo-inositol 1,4,5- and 2,4,5-trisphosphates, 1,4-bisphosphate 5-phosphorothioate, and 4,5-bisphosphate 1-phosphorothioate from 1D-3,6-di-O-benzyl-1,2-O-isopropylidene-myo-inositol.由1D-3,6-二-O-苄基-1,2-O-异亚丙基-myo-肌醇制备用于合成1D-肌醇1,4,5-三磷酸酯、2,4,5-三磷酸酯、1,4-二磷酸酯5-硫代磷酸酯和4,5-二磷酸酯1-硫代磷酸酯的中间体。
Carbohydr Res. 1994 Sep 1;262(1):59-77. doi: 10.1016/0008-6215(94)84005-9.
3
Deoxygenated phosphorothioate inositol phosphate analogs: synthesis, phosphatase stability, and binding affinity.脱氧硫代磷酸肌醇磷酸类似物：合成、磷酸酶稳定性及结合亲和力。
Bioorg Med Chem. 2008 Mar 15;16(6):3419-27. doi: 10.1016/j.bmc.2007.10.032. Epub 2007 Oct 14.
4
Synthesis and iron binding studies of myo-inositol 1,2,3-trisphosphate and (+/-)-myo-inositol 1,2-bisphosphate, and iron binding studies of all myo-inositol tetrakisphosphates.肌醇1,2,3-三磷酸酯和（±）-肌醇1,2-二磷酸酯的合成及铁结合研究，以及所有肌醇四磷酸酯的铁结合研究。
Carbohydr Res. 1996 Feb 28;282(1):81-99. doi: 10.1016/0008-6215(95)00361-4.
5
Chiral synthesis of D- and L-myo-inositol 1,4,5-trisphosphate.D-和L-肌醇1,4,5-三磷酸的手性合成。
Proc Natl Acad Sci U S A. 1989 Jan;86(1):94-8. doi: 10.1073/pnas.86.1.94.
6
(+/-)-1,2:5,6-Di-O-isopropylidene-myo-inositol and (+/-)-6-O-benzoyl-1,2:4,5-di-O-isopropylidene-myo-inositol: a practical preparation of key intermediates for myo-inositol phosphates.（±）-1,2:5,6-二-O-异亚丙基-myo-肌醇和（±）-6-O-苯甲酰基-1,2:4,5-二-O-异亚丙基-myo-肌醇：肌醇磷酸关键中间体的实用制备方法
Carbohydr Res. 2002 Jan 7;337(1):75-8. doi: 10.1016/s0008-6215(01)00286-5.
7
The preparation and phosphorylation of 2,5- and 1D-2,6-di-O-benzyl-myo-inositol.2,5-和1D-2,6-二-O-苄基-myo-肌醇的制备与磷酸化
Carbohydr Res. 1992 Apr 10;228(1):65-79. doi: 10.1016/s0008-6215(00)90549-4.
8
Synthesis of 3-Position-Modified Analogues of myo-Inositol 1,4,5-Trisphosphate, Tools for Investigation of the Polyphosphoinositide Pathway of Cellular Signaling.肌醇1,4,5-三磷酸3-位修饰类似物的合成，细胞信号转导多磷酸肌醇途径研究工具
J Org Chem. 1997 Nov 28;62(24):8335-40. doi: 10.1021/jo970926y.
9
Divergent syntheses of all possible optically active regioisomers of myo-inositol tris- and tetrakisphosphates.肌醇三磷酸酯和四磷酸酯所有可能的旋光区域异构体的发散合成。
J Org Chem. 2002 Aug 9;67(16):5626-37. doi: 10.1021/jo0257694.
10
Inositol(3,4)bisphosphate and inositol(1,3)bisphosphate in GH4 cells--evidence for complex breakdown of inositol(1,3,4)trisphosphate.生长激素分泌细胞中的肌醇（3,4）二磷酸和肌醇（1,3）二磷酸——肌醇（1,3,4）三磷酸复杂分解的证据
Biochem Biophys Res Commun. 1987 Feb 27;143(1):353-9. doi: 10.1016/0006-291x(87)90672-3.

引用本文的文献

1
Stereospecific mobilization of intracellular Ca2+ by inositol 1,4,5-triphosphate. Comparison with inositol 1,4,5-trisphosphorothioate and inositol 1,3,4-trisphosphate.肌醇1,4,5-三磷酸对细胞内Ca2+的立体特异性动员。与肌醇1,4,5-三硫代磷酸酯和肌醇1,3,4-三磷酸的比较。
Biochem J. 1988 Aug 1;253(3):901-5. doi: 10.1042/bj2530901.
2
Fructose 2,6-bisphosphate and its phosphorothioate analogue. Comparison of their hydrolysis and action on glycolytic and gluconeogenic enzymes.果糖2,6 -二磷酸及其硫代磷酸酯类似物。它们的水解以及对糖酵解和糖异生酶作用的比较。
Biochem J. 1988 Jul 15;253(2):597-601. doi: 10.1042/bj2530597.
3
Inositol 1,3,4,5-tetrakisphosphate is essential for sustained activation of the Ca2+-dependent K+ current in single internally perfused mouse lacrimal acinar cells.肌醇1,3,4,5-四磷酸对于单个经内部灌注的小鼠泪腺腺泡细胞中Ca2+依赖性钾电流的持续激活至关重要。
J Membr Biol. 1989 Jul;109(1):85-93. doi: 10.1007/BF01870793.
4
Ca2+ release by inositol-trisphosphorothioate in isolated triads of rabbit skeletal muscle.肌醇三磷酸硫代物在兔骨骼肌分离三联体中的钙离子释放
Biophys J. 1990 Jun;57(6):1233-43. doi: 10.1016/S0006-3495(90)82642-4.
5
Two-dimensional model of calcium waves reproduces the patterns observed in Xenopus oocytes.钙波的二维模型再现了非洲爪蟾卵母细胞中观察到的模式。
Biophys J. 1992 Feb;61(2):509-17. doi: 10.1016/S0006-3495(92)81855-6.

本文引用的文献

1
Myo-inositol phosphates obtained by alkaline hydrolysis of beef brain phosphoinositide.通过牛肉脑磷酸肌醇碱性水解得到的肌醇磷酸酯。
J Biol Chem. 1961 Jan;236:54-60.
2
Release of Ca2+ from a nonmitochondrial intracellular store in pancreatic acinar cells by inositol-1,4,5-trisphosphate.1,4,5-三磷酸肌醇促使胰腺腺泡细胞非线粒体胞内钙库释放钙离子。
Nature. 1983;306(5938):67-9. doi: 10.1038/306067a0.
3
Polymer support oligonucleotide synthesis XVIII: use of beta-cyanoethyl-N,N-dialkylamino-/N-morpholino phosphoramidite of deoxynucleosides for the synthesis of DNA fragments simplifying deprotection and isolation of the final product.聚合物载体寡核苷酸合成 XVIII：脱氧核苷的β-氰基乙基-N，N-二烷基氨基-/N-吗啉代亚磷酰胺用于 DNA 片段合成，简化最终产物的脱保护和分离
Nucleic Acids Res. 1984 Jun 11;12(11):4539-57. doi: 10.1093/nar/12.11.4539.
4
Inositol trisphosphates in carbachol-stimulated rat parotid glands.卡巴胆碱刺激的大鼠腮腺中的肌醇三磷酸
Biochem J. 1984 Oct 1;223(1):237-43. doi: 10.1042/bj2230237.
5
Stepwise enzymatic dephosphorylation of inositol 1,4,5-trisphosphate to inositol in liver.肝脏中肌醇1,4,5-三磷酸逐步酶促脱磷酸生成肌醇的过程。
Nature. 1984;312(5992):374-6. doi: 10.1038/312374a0.
6
Inositol trisphosphate, a novel second messenger in cellular signal transduction.肌醇三磷酸，细胞信号转导中的一种新型第二信使。
Nature. 1984;312(5992):315-21. doi: 10.1038/312315a0.
7
Nucleoside phosphorothioates.硫代磷酸核苷
J Am Chem Soc. 1970 Jul 29;92(15):4718-23. doi: 10.1021/ja00718a039.
8
Adenosine 5'-O(3-thiotriphosphate) in the control of phosphorylase activity.5'-O(3-硫代三磷酸)腺苷对磷酸化酶活性的调控
Biochem Biophys Res Commun. 1974 Jun 18;58(4):960-7. doi: 10.1016/s0006-291x(74)80237-8.
9
Rapid formation of inositol 1,3,4,5-tetrakisphosphate following muscarinic receptor stimulation of rat cerebral cortical slices.毒蕈碱受体刺激大鼠大脑皮层切片后肌醇1,3,4,5-四磷酸的快速形成。
Biochem J. 1985 Nov 15;232(1):211-5. doi: 10.1042/bj2320211.
10
Micro-injection of inositol 1,3,4,5-tetrakisphosphate activates sea urchin eggs by a mechanism dependent on external Ca2+.微量注射肌醇1,3,4,5 - 四磷酸通过一种依赖于细胞外钙离子的机制激活海胆卵。
Biochem J. 1986 Dec 15;240(3):917-20. doi: 10.1042/bj2400917.

肌醇硫代磷酸酯，肌醇磷酸酯的抗磷酸酶类似物。DL-肌醇1,4-二磷酸酯和DL-肌醇1,4-二硫代磷酸酯的合成。

myo-Inositol phosphorothioates, phosphatase-resistant analogues of myo-inositol phosphates. Synthesis of DL-myo-inositol 1,4-bisphosphate and DL-myo-inositol 1,4-bisphosphorothioate.

作者信息

Hamblin M R, Flora J S, Potter B V

机构信息

Department of Chemistry, Leicester University, U.K.

出版信息

Biochem J. 1987 Sep 15;246(3):771-4. doi: 10.1042/bj2460771.

DOI:10.1042/bj2460771
PMID:3689330
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC1148343/
Abstract

Syntheses of a metabolite of the second messenger myo-inositol 1,4,5-trisphosphate, myo-inositol 1,4-bisphosphate, and an analogue, the 1,4-bisphosphorothioate, are reported, by using phosphite chemistry on (+/-)-1,2:4,5-di-isopropylidene-myo-inositol. The synthesis of (+/-)-1,2:4,5-di-isopropylidene 3,6-bis[di-(2-cyanoethyl)]phosphite provides an intermediate that can be oxidized to either the corresponding bisphosphate or bisphosphorothioate. myo-Inositol phosphorothioates are proposed as novel analogues of myo-inositol phosphates; their resistance to phosphatase-catalysed breakdown is reported.

摘要

报道了通过对（±）-1,2:4,5-二异亚丙基-myo-肌醇使用亚磷酸酯化学方法合成第二信使肌醇1,4,5-三磷酸的代谢产物肌醇1,4-二磷酸及其类似物1,4-二硫代磷酸酯。（±）-1,2:4,5-二异亚丙基3,6-双[二（2-氰基乙基）]亚磷酸酯的合成提供了一种中间体，该中间体可被氧化为相应的二磷酸酯或二硫代磷酸酯。肌醇硫代磷酸酯被认为是肌醇磷酸酯的新型类似物；报道了它们对磷酸酶催化分解的抗性。