MYOINOSOSE (D) | 488-66-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: MYOINOSOSE (D)
• 英文别名: (2R)-2r,3c,4t,5c,6t-pentahydroxy-cyclohexanone；(2R)-2r,3c,4t,5c,6t-Pentahydroxy-cyclohexanon；L-myo-Inosose-(1)
• CAS: 488-66-4
• 化学式: C₆H₁₀O₆
• 分子量: 178.142
• InChiKey: VYEGBDHSGHXOGT-QFYCRYKCSA-N

物化性质

• 沸点：
  368.6±42.0 °C(Predicted)
• 密度：
  2.026±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.63
• 重原子数：
  12.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  118.22
• 氢给体数：
  5.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  MYOINOSOSE (D) 生成 (-)-1-deoxy-1-amino-myo-inositol
  参考文献：
  名称：

  Total Synthesis of Minosaminomycin

  摘要：

  抗生素米诺霉素 (1), (−)-1d-1-氨基-1-脱氧肌醇 (4) 的成分是由 d-肌醇 (3) 通过轴向羟基的催化氧化和还原合成的酮肟。氨基二糖胺，1d-1-氨基-1-脱氧-4-O-(α-d-kasugaminyl)-myo-inositol (2)，由 2',4'-di-N-乙酰春日二糖胺 (9) 合成，通过类似的方法，从2的两个异构体中分离出来。1的全合成是通过2',4'-二-N-苄氧基羰基氨基二糖胺(14)与Nα-[(S)-1-苄氧基羰基-3-甲基丁基氨基甲酰基的偶联完成的。 ]enduracididine (15)，然后除去保护基团。化合物14是由1,2',4'-三-N-苄氧基羰基氨基二糖胺通过顺式-1,2-氨基甲酸酯的形成而衍生的。还使用alloenduracididine 合成了1 的非对映异构体。

  DOI：

  10.1246/bcsj.50.1850
• 作为产物：
  描述：

  肌糖 在 platinum on activated charcoal 氧气 作用下， 以 水 为溶剂， 生成 MYOINOSOSE (D)
  参考文献：
  名称：

  Cyclitols and their Methyl Ethers. III. Catalytic Air Oxidation, the Hydrogenolysis of Inososes, and Some Pentol and Tetrol Methyl Ethers^1-3

  摘要：

  DOI：

  10.1021/ja00862a030

文献信息

• Recherches dans la série des cyclitols XIII. Préparation et oxydation biochimique du<i>d</i>-viburnitol
  作者：Théodore Posternak

  DOI：10.1002/hlca.19500330627

  日期：——

  L'hydrogénation catalytique du d-inosose en milieu fortement acide fournit du d-viburnitol. Sous l'action d'Acetobacter suboxydans, les d- et l-viburnitols se transforment en deux tétrahydroxy-cyclohexanones énantiomorphes.

  L'氢化catalytique杜d -inosose烯环境fortement酸fournit杜d -viburnitol。苏L'行动d'醋酸菌，LES d -等升-viburnitols SE transforment EN德塞夫勒四羟基-环己酮énantiomorphes。
• Genetic Modification of <i>Bacillus subtilis</i> for Production of <scp>d</scp> - <i>chiro</i> -Inositol, an Investigational Drug Candidate for Treatment of Type 2 Diabetes and Polycystic Ovary Syndrome
  作者：Ken-ichi Yoshida、Masanori Yamaguchi、Tetsuro Morinaga、Maya Ikeuchi、Masaki Kinehara、Hitoshi Ashida

  DOI：10.1128/aem.72.2.1310-1315.2006

  日期：2006.2

  d - chiro -Inositol (DCI) is a drug candidate for the treatment of type 2 diabetes and polycystic ovary syndrome, since it improves the efficiency with which the body uses insulin and also promotes ovulation. Here, we report genetic modification of Bacillus subtilis for production of DCI from myo -inositol (MI). The B. subtilis iolABCDEFGHIJ operon encodes enzymes for the multiple steps of the MI catabolic pathway. In the first and second steps, MI is converted to 2-keto-MI (2KMI) by IolG and then to 3 d -(3,5/4)-trihydroxycyclohexane-1,2-dione by IolE. In this study, we identified iolI encoding inosose isomerase, which converts 2KMI to 1-keto- d - chiro -inositol (1KDCI), and found that IolG reduces 1KDCI to DCI. Inactivation of iolE in a mutant constitutively expressing the iol operon blocked the MI catabolic pathway to accumulate 2KMI, which was converted to DCI via the activity of IolI and IolG. The mutant was able to convert at least 6% of input MI in the culture medium to DCI.

  摘要 d - 肌醇 -肌醇（DCI）是治疗 2 型糖尿病和多囊卵巢综合征的候选药物，因为它能提高机体利用胰岛素的效率，还能促进排卵。在此，我们报告了对 枯草芽孢杆菌 生产 DCI 肌醇 -肌醇（MI）生产 DCI。该 B. subtilis iolABCDEFGHIJ 操作子编码 MI 分解途径多个步骤的酶。在第一步和第二步中，MI 被 IolG 转化为 2-酮-MI（2KMI），然后转化为 3 d -(3,5/4)-三羟基环己烷-1,2-二酮。在这项研究中，我们确定了 iolI 编码肌糖异构酶，该酶将 2KMI 转化为 1-keto- d - 肌醇 -肌醇（1KDCI），并发现 IolG 能将 1KDCI 还原成 DCI。灭活 iolE 的失活。 iol 突变体能够将培养基中至少 6% 的 MI 转化为 DCI。
• Magasanik; Chargaff, Journal of Biological Chemistry, 1948, vol. 175, p. 939,942
  作者：Magasanik、Chargaff

  DOI：——

  日期：——
• Magasanik; Chargaff, Journal of Biological Chemistry, 1948, vol. 174, p. 173,176, 179
  作者：Magasanik、Chargaff

  DOI：——

  日期：——
• myo-Inositol Catabolism in Bacillus subtilis
  作者：Ken-ichi Yoshida、Masanori Yamaguchi、Tetsuro Morinaga、Masaki Kinehara、Maya Ikeuchi、Hitoshi Ashida、Yasutaro Fujita

  DOI：10.1074/jbc.m708043200

  日期：2008.4

  The iolABCDEFGHIJ operon of Bacillus subtilis is responsible for myo-inositol catabolism involving multiple and stepwise reactions. Previous studies demonstrated that IolG and IolE are the enzymes for the first and second reactions, namely dehydrogenation of myo-inositol to give 2-keto-myo-inositol and the subsequent dehydration to 3D-(3,5/4)-trihydroxycyclohexane1,2- dione. In the present studies the third reaction was shown to be the hydrolysis of 3D-(3,5/4)-trihydroxycyclohexane-1,2-dione catalyzed by IolD to yield 5-deoxy-D-glucuronic acid. The fourth reaction was the isomerization of 5-deoxy-D-glucuronic acid by IolB to produce 2-deoxy-5-keto-D-gluconic acid. Next, in the fifth reaction 2-deoxy-5-keto-D-gluconic acid was phosphorylated by IolC kinase to yield 2-deoxy-5-keto-D-gluconic acid 6-phosphate. IolR is known as the repressor controlling transcription of the iol operon. In this reaction 2-deoxy-5-keto-D-gluconic acid 6-phosphate appeared to be the intermediate acting as inducer by antagonizing DNA binding of IolR. Finally, IolJ turned out to be the specific aldolase for the sixth reaction, the cleavage of 2-deoxy-5-keto-D-gluconic acid 6-phosphate into dihydroxyacetone phosphate and malonic semialdehyde. The former is a known glycolytic intermediate, and the latter was previously shown to be converted to acetyl-CoA and CO2 by a reaction catalyzed by IolA. The net result of the inositol catabolic pathway in B. subtilis is, thus, the conversion of myo-inositol to an equimolar mixture of dihydroxyacetone phosphate, acetyl-CoA, and CO2.