放线硫醇
化合物
放线硫醇（英语：Mycothiol，缩写为MSH），也译作真菌硫醇、分支硫醇、AcCys-GlcN-Ins等，是放线菌中发现的一种不寻常的硫醇化合物。[1][2]它由一个半胱氨酸残基和一个与葡萄糖胺连接的乙酰化氨基组成，然后与肌醇连接。[3]氧化的二硫化物形式的放线硫醇（MSSM）称为放线硫酮，并被黄素蛋白放线硫酮还原酶还原为放线硫醇。[4][5]放线硫醇生物合成和放线硫醇依赖性酶（例如放线硫醇依赖性甲醛脱氢酶和放线硫酮还原酶）已被认为是开发结核病治疗的良好药物靶点。[6][7][8]
| 放线硫醇 | |||
|---|---|---|---|
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| IUPAC名 (2R)-2-acetamido-N-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[(2R,3S,5R,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxyoxan-3-yl]-3-sulfanylpropanamide | |||
| 别名 | 真菌硫醇、分支硫醇、AcCys-GlcN-Ins | ||
| 识别 | |||
| CAS号 | 192126-76-4 
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| PubChem | 441148 | ||
| ChemSpider | 10193006 | ||
| SMILES |
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| InChI |
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| InChIKey | MQBCDKMPXVYCGO-FQBKTPCVBG | ||
| ChEBI | 16768 | ||
| KEGG | C06717 | ||
| 性质 | |||
| 化学式 | C17H30N2O12S | ||
| 摩尔质量 | 486.49 g/mol g·mol⁻¹ | ||
| 若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。 | |||
参见 编辑
参考资料 编辑
- ^ Fahey RC. Novel thiols of prokaryotes. Annu. Rev. Microbiol. 2001, 55: 333–56. PMID 11544359. doi:10.1146/annurev.micro.55.1.333.
- ^ Jothivasan VK, Hamilton CJ, (2008) Mycothiol: synthesis, biosynthesis and biological functions of the major low molecular weight thiol in actinomycetes. Natural Product Reports, (25). 1091-1117 [1]
- ^ Newton GL, Buchmeier N, Fahey RC. Biosynthesis and functions of mycothiol, the unique protective thiol of Actinobacteria. Microbiol. Mol. Biol. Rev. September 2008, 72 (3): 471–94. PMC 2546866
. PMID 18772286. doi:10.1128/MMBR.00008-08.
- ^ Patel MP, Blanchard JS. Expression, purification, and characterization of Mycobacterium tuberculosis mycothione reductase. Biochemistry. September 1999, 38 (36): 11827–33. PMID 10512639. doi:10.1021/bi991025h.
- ^ Patel MP, Blanchard JS. Mycobacterium tuberculosis mycothione reductase: pH dependence of the kinetic parameters and kinetic isotope effects. Biochemistry. May 2001, 40 (17): 5119–26. PMID 11318633. doi:10.1021/bi0029144.
- ^ Rawat M, Av-Gay Y. Mycothiol-dependent proteins in actinomycetes. FEMS Microbiol. Rev. April 2007, 31 (3): 278–92. PMID 17286835. doi:10.1111/j.1574-6976.2006.00062.x .
- ^ Newton GL, Fahey RC. Mycothiol biochemistry. Arch. Microbiol. December 2002, 178 (6): 388–94. PMID 12420157. S2CID 23893254. doi:10.1007/s00203-002-0469-4.
- ^ Vilchèze, Catherine; Hartman, Travis; Weinrick, Brian; Jacobs, William R. Mycobacterium tuberculosis is extraordinarily sensitive to killing by a vitamin C-induced Fenton reaction. Nature Communications. 2013-05-21, 4 (1) [2023-10-06]. ISSN 2041-1723. PMC 3698613 . PMID 23695675. doi:10.1038/ncomms2898. （原始内容存档于2016-12-14） （英语）.
