mycothiol | 192126-76-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: mycothiol
• CAS: 192126-76-4
• 化学式: C₁₇H₃₀N₂O₁₂S
• 分子量: 486.49238
• InChiKey: MQBCDKMPXVYCGO-FQBKTPCVSA-N

物化性质

• 沸点：
  862.1±65.0 °C(Predicted)
• 密度：
  1.66±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -6.45
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  238.5
• 氢给体数：
  11.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 mycothiol 生成 S-(hydroxymethyl)mycothiol
  参考文献：
  名称：

  分枝杆菌中亚硝基硫醇的代谢：S-亚硝基硫醇还原酶的鉴定和表征。

  摘要：

  在培养物中，耻垢分枝杆菌将S-亚硝基谷胱甘肽代谢为氧化型谷胱甘肽和硝酸盐，这表明S-亚硝基硫醇还原酶和分枝杆菌血红蛋白可能参与其中。通过结合Ni2 + -IMAC（固定化金属离子亲和色谱），疏水相互作用，阴离子交换和亲和色谱纯化来自耻垢分枝杆菌的依赖于硫醇的甲醛脱氢酶。该酶的亚基分子量为38263 kDa。稳态动力学研究表明，该酶通过快速平衡有序机制催化NAD +依赖性的S-羟甲基霉菌硫醇转化为甲酸和霉菌硫醇。该酶还通过顺序机制和等摩尔化学计量的NADH：MSNO催化了NA-依赖性的S-亚硝基硫醇（MSNO）分解，这表明该酶将亚硝基还原为硝酰的氧化水平。MSNO还原酶反应的Vmax表示每个亚基的周转量约为。116700分钟（-1），比甲醛脱氢酶活性快76倍。克隆了在结核分枝杆菌基因组中标注为III类醇脱氢酶的基因Rv2259，并在耻垢分枝杆菌中将其表达为C端带有His6标签的产物。来自结核

  DOI：

  10.1042/bj20030642
• 作为产物：
  描述：

  1D-myo-inositol 2-(L-cysteinylamino)-2-deoxy-α-D-glucopyranoside 、 (2R)-N-[3-(2-acetylsulfanylethylimino)-3-oxidopropyl]-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonatooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanimidate 生成 coenzyme A 、 氢(+1)阳离子 、 mycothiol
  参考文献：
  名称：

  Identification of the mycothiol synthase gene ( mshD ) encoding the acetyltransferase producing mycothiol in actinomycetes

  摘要：

  Mycothiol is the predominant thiol in most actinomycetes, including Mycobacterium tuberculosis, and appears to play a role analogous to glutathione, which is not found in these bacteria. The enzymes involved in mycothiol biosynthesis are of interest as potential targets for new drugs directed against tuberculosis. In this work we describe the isolation and characterization of a Tn5 transposon mutant of Mycobacterium smegmatis that is blocked in the production of mycothiol and accumulates its precursor, 1D-myo-inosityl 2-L-cysteinylamido-2-deoxy-alpha-D-glucopyranoside (Cys-GlcN-Ins). Cys-GlcN-Ins isolated from this mutant was used to assay for acetyl-CoA:Cys-GlcN-Ins acetyltransferase (mycothiol synthase, MshD) activity, which was found in wild-type cells, but not in the mutant. Sequencing outward of the DNA of the mutant strain from the site of insertion permitted identification of the mshD gene in the M. smegmatis genome, as well as the orthologous gene Rv0819 in the M. tuberculosis genome. Cloning and expression of mshD from M. tuberculosis (Rv0819) in Escherichia coli gave a transformant with MshD activity, demonstrating that Rv0819 is the mshD mycothiol biosynthesis gene.

  DOI：

  10.1007/s00203-002-0462-y

文献信息

• Inositol Biotransformation
  申请人：UNIVERSITY COURT OF THE UNIVERSITY OF ST ANDREWS

  公开号：US20160168607A1

  公开（公告）日：2016-06-16

  Disclosed is a method of preparing pure or substantially pure D-myo-inositol-3-phosphate from glucose-6-phosphate and/or fructose-6-phosphate. The method may also be applied to protected and/or derivative forms of glucose-6-phosphate and/or fructose-6-phosphate so as to form protected/derivative forms of D-myo-inositol-3-phosphate, for use in further chemical reactions. The enzyme D-myo-inositol-3-phosphate synthase (INO1) is contacted with the glucose-6-phosphate and/or fructose-6-phosphate to generate labeled or unlabeled, protected or unprotected D-myo-inositol-3-phosphate, which may be further reacted and/or purified.

  披露了一种从葡萄糖-6-磷酸和/或果糖-6-磷酸制备纯净或基本纯净的D-肌醇-3-磷酸的方法。该方法也可应用于葡萄糖-6-磷酸和/或果糖-6-磷酸的保护形式和/或衍生物形式，以形成D-肌醇-3-磷酸的保护/衍生物形式，用于进一步的化学反应。D-肌醇-3-磷酸合酶（INO1）酶与葡萄糖-6-磷酸和/或果糖-6-磷酸接触，以生成标记的或未标记的、保护的或未保护的D-肌醇-3-磷酸，该磷酸可进一步反应和/或纯化。
• [EN] GOLD COMPOUNDS AND THEIR USE IN THERAPY<br/>[FR] COMPOSÉS D'OR ET LEUR UTILISATION DANS LE CADRE D'UNE THÉRAPIE
  申请人：AUSPHERIX LTD

  公开号：WO2018220171A1

  公开（公告）日：2018-12-06

  Compound of formula (I) and pharmaceutically acceptable salts and solvates thereof are described, wherein: Px selected from (P1), (P2) or (P3); The compounds are useful in the prevention or treatment of a bacterial infection.

  描述了化合物的公式（I）及其药用可接受的盐和溶剂化合物，其中：Px选自（P1）、（P2）或（P3）；这些化合物在预防或治疗细菌感染方面是有用的。
• N-alkylthio beta-lactams, alkyl-coenzyme a asymmetric disulfides, and aryl-alkyl disulfides as anti-bacterial agents
  申请人：Turos Edward

  公开号：US20080182815A1

  公开（公告）日：2008-07-31

  The present invention provides N-alkylthio β-lactams and disulfide compounds (e.g., alkyl-coenzyme A asymmetric disulfides or aryl-alkyl disulfides), compositions containing such compounds, and method of their use as anti-bacterial agents.

  本发明提供了N-烷基硫代β-内酰胺和二硫化合物（例如，烷基辅酶A不对称二硫化合物或芳基-烷基二硫化合物），含有这些化合物的组合物，以及将它们用作抗菌剂的方法。
• THIOL MEDIATED/ACTIVATED PRODRUGS OF SULFUR DIOXIDE (SO2) HAVING ANTI-BACTERIAL ACTIVITY
  申请人：INDIAN INSTITUTE OF SCIENCE EDUCATION AN

  公开号：US20140121211A1

  公开（公告）日：2014-05-01

  Disclosed herein are thiol mediated/activated prodrugs of SO 2 , particularly 2,4-dinitrophenylsulfonamide analogues, having Formula-I or pharmaceutically acceptable salts thereof exhibiting tunable release profiles of SO 2 with significant therapeutic efficacy against bacterial infections. Further, the present invention provides pharmaceutical compositions comprising compound of Formula I or pharmaceutically acceptable salts thereof, along with pharmaceutically acceptable carriers/excipients.

  本文披露了硫醇介导/激活的SO2前药，尤其是2,4-二硝基苯磺酰胺类似物，具有公式I或其药学上可接受的盐，表现出可调节的SO2释放剖面，并对细菌感染具有显著的治疗功效。此外，本发明提供了包含公式I化合物或其药学上可接受的盐的制药组合物，以及药学上可接受的载体/赋形剂。
• Manipulating nitrosative stress to kill pathologic microbes, pathologic helminths and pathologically proliferating cells or to upregulate nitrosative stress defenses
  申请人：——

  公开号：US20030207815A1

  公开（公告）日：2003-11-06

  Mammals are treated for infections or for conditions associated with pathologically proliferating mammalian cell growth (for example certain cancers, restenosis, benign prostatic hypertrophy) by administration of a manipulator of nitrosative stress to selectively kill or reduce the growth of the microbes or helminths causing the infection or of host cells infected with the microbes or of the pathologically proliferating mammalian cells. Novel agents include &agr;-alkyl-S-alkyl-homocysteine sulfoximines wherein the &agr;-alkyl contains 2 to 8 carbon atoms, and the S-alkyl-contains 1 to 10 carbon atoms. In another invention herein, mammals in need of increased nitrosative stress defenses are treated, e.g., humans at risk for a stroke because of having had a transient ischemic attack, are treated. Treatments to increase nitrosative stress defenses include, for example, repeated administrations of low doses of manipulators of nitrosative stress so that the subject treated has increased tolerance to nitrosative stress. In still another invention, mammals are treated for protozoal infections by systemic administration of L-buthionine-S-sulfoximine and agent that increases nitrosative stress.

  哺乳动物被治疗感染或与病理增殖哺乳动物细胞生长相关的情况（例如某些癌症，再狭窄，良性前列腺增生）通过给予一种硝化应激调节剂，以选择性地杀死或减少微生物或蠕虫引起的感染或受微生物感染的宿主细胞或病理增殖的哺乳动物细胞的生长。新型药剂包括α-烷基-S-烷基-同型半胱氨酸亚砜，其中α-烷基含2至8个碳原子，S-烷基含1至10个碳原子。在本发明的另一种方法中，需要增加硝化应激防御的哺乳动物被治疗，例如，由于患有短暂性缺血性发作而处于中风风险的人类被治疗。增加硝化应激防御的治疗包括例如反复给予低剂量的硝化应激调节剂，以使受治疗的对象对硝化应激具有增加的耐受性。在另一种发明中，哺乳动物通过系统给药L-丁硫氧嘧啶和增加硝化应激的药物来治疗原虫感染。