放线硫醇

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
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。

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）和放线硫酮还原酶（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]

参见

谷胱甘肽
芽孢杆菌硫醇（英语：Bacillithiol）

参考资料

^ 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）.

外部链接

The Biochemistry of Pathogens: The metabolism and function of mycothiol in the mycobacteria.

[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）.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]