放線硫醇

放線硫醇
	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
別名	真菌硫醇、分支硫醇、AcCys-GlcN-Ins
識別
CAS號	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
性質
化學式	C17H30N2O12S
莫耳質量	486.49 g/mol g·mol⁻¹
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

放線硫醇（英語：Mycothiol，縮寫為MSH），也譯作真菌硫醇、分支硫醇、AcCys-GlcN-Ins等，是放線菌中發現的一種不尋常的硫醇化合物。^[1]^[2]它由一個半胱氨酸殘基和一個與葡萄糖胺連接的乙醯化氨基組成，然後與肌醇連接。^[3]氧化的二硫化物形式的放線硫醇（MSSM）稱為放線硫酮，並被黃素蛋白放線硫酮還原酶還原為放線硫醇。^[4]^[5]放線硫醇生物合成和放線硫醇依賴性酶（例如放線硫醇依賴性甲醛脫氫酶（英語：Mycothiol-dependent formaldehyde dehydrogenase）和放線硫酮還原酶（英語：Mycothione reductase））已被認為是開發結核病治療的良好藥物靶點。^[6]^[7]^[8]

參見[編輯]

穀胱甘肽
芽孢桿菌硫醇（英語：Bacillithiol）

參考資料[編輯]

^ 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. （原始內容存檔於2016-12-14）（英語）.

外部連結[編輯]

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. （原始內容存檔於2016-12-14）（英語）.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]