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英语Mycothiol-dependent formaldehyde dehydrogenase放线硫酮还原酶英语Mycothione reductase)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
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  checkY
PubChem 441148
ChemSpider 10193006
SMILES
 
  • CC(=O)N[C@@H](CS)C(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@@H]1O[C@@H]2[C@@H]([C@@H]([C@H]([C@@H]([C@H]2O)O)O)O)O)CO)O)O
InChI
 
  • 1/C17H30N2O12S/c1-4(21)18-5(3-32)16(29)19-7-9(23)8(22)6(2-20)30-17(7)31-15-13(27)11(25)10(24)12(26)14(15)28/h5-15,17,20,22-28,32H,2-3H2,1H3,(H,18,21)(H,19,29)/t5-,6+,7+,8+,9+,10-,11-,12+,13+,14+,15-,17+/m0/s1
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

参考资料

  1. ^ Fahey RC. Novel thiols of prokaryotes. Annu. Rev. Microbiol. 2001, 55: 333–56. PMID 11544359. doi:10.1146/annurev.micro.55.1.333. 
  2. ^ 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]
  3. ^ 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. 
  4. ^ 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. 
  5. ^ 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. 
  6. ^ 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 . 
  7. ^ 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. 
  8. ^ 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). 

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