2-deoxy-scyllo-inosamine | 76188-89-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-deoxy-scyllo-inosamine
• 英文别名: (1R,2S,3S,4R,5S)-5-aminocyclohexane-1,2,3,4-tetrol
• CAS: 76188-89-1
• 化学式: C₆H₁₃NO₄
• 分子量: 163.174
• InChiKey: QXQNRSUOYNMXDL-KGJVWPDLSA-N

物化性质

• 沸点：
  301.9±42.0 °C(Predicted)
• 密度：
  1.600±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  107
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-deoxy-scyllo-inosamine 在 BtrN from Bacillus circulans 、 S-腺苷蛋氨酸 作用下， 生成 (2R,3S,4R,5S)-5-amino-2,3,4-trihydroxycyclohexanone
  参考文献：
  名称：

  Electrochemical Resolution of the [4Fe-4S] Centers of the AdoMet Radical Enzyme BtrN: Evidence of Proton Coupling and an Unusual, Low-Potential Auxiliary Cluster

  摘要：

  The S-adenosylmethionine (AdoMet) radical superfamily of enzymes includes over 113 500 unique members, each of which contains one indispensable iron-sulfur (FeS) cluster that is required to generate a 5'-deoxyadenosyl 5'-radical intermediate during catalysis. Enzymes within several subgroups of the superfamily, however, have been found to contain one or more additional FeS clusters. While these additional clusters are absolutely essential for enzyme activity, their exact roles in the function and/or mechanism of action of many of the enzymes are at best speculative, indicating a need to develop methods to characterize and study these clusters in more detail. Here, BtrN, an AdoMet radical dehydrogenase that catalyzes the two-electron oxidation of 2-deoxy-scyllo-inosamine to amino-dideoxy-scyllo-inosose, an intermediate in the biosynthesis of 2-deoxystreptamine antibiotics, is examined through direct electrochemistry, where the potential of both its AdoMet radical and auxiliary [4Fe-4S] clusters can be measured simultaneously. We find that the AdoMet radical cluster exhibits a midpoint potential of -510 mV, while the auxiliary cluster exhibits a midpoint potential of -765 mV, to our knowledge the lowest [4Fe-4S](2+/+) potential to be determined to date. The impact of AdoMet binding and the pH dependence of catalysis are also quantitatively observed. These data show that direct electrochemical methods can be used to further elucidate the chemistry of the burgeoning AdoMet radical superfamily in the future.

  DOI：

  10.1021/jacs.5b03384
• 作为产物：
  描述：

  Inositol 在 palladium on activated charcoal 吡啶 、 sodium hydroxide 、 sodium azide 、 苄基三乙基氯化铵 、 氢气 、 二正丁基氧化锡 、 三乙基硼氢化锂 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 盐酸 、 甲醇 、 氯仿 、 水 、 溶剂黄146 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 2-deoxy-scyllo-inosamine
  参考文献：
  名称：

  方便合成的2-脱氧青蟹-inosose和2-脱氧青蟹-inosamine：对生物合成途径的氨基糖苷类抗生素的两个关键中间体

  摘要：

  2-脱氧青蟹-inosose 1和2-脱氧青蟹-inosamine 2是含2脱氧链霉胺氨基糖苷类抗生素两个在生物合成途径中的关键中间体的对。的方便合成1，2和氚标记的2经由立体选择性脱氧肌使用LTBH肌醇报告。这应该提供表征生物合成途径所涉及的酶所必需的底物。

  DOI：

  10.1016/s0040-4039(01)00612-8

文献信息

• Isolation of Nabscessin C from <i>Nocardia abscessus</i> IFM 10029<sup>T</sup> and a Study on Biosynthetic Pathway for Nabscessins
  作者：Shoko Hara、Yasumasa Hara、Midori A. Arai、Yoko Kusuya、Hiroki Takahashi、Takashi Yaguchi、Masami Ishibashi

  DOI：10.1248/cpb.c18-00430

  日期：2018.10.1

  derivative, designated nabscessin C (1), was isolated from Nocardia abscessus IFM 10029T. Nabcessin C is an isomer of nabscessins A (2) and B (3) with different positioning of the acyl group. Absolute configuration of nabscessin A was determined by conversion into the 2-deoxy-scyllo-inosamine pentaacetyl derivative (4) by hydrolysis and acetylation of 2. The biosynthetic pathway of nabscessins is proposed

  从脓肿诺卡氏菌IFM 10029T中分离出一种新的氨基环醇衍生物，命名为nabscessin C（1）。萘丁香素C是萘丁香素A（2）和B（3）的异构体，其酰基具有不同的位置。通过2的水解和乙酰化转化为2-脱氧-鞘氨醇五乙酰基衍生物（4），确定了纳豆素A的绝对构型。基于基因表达分析，提出了纳豆素的生物合成途径。
• Biosynthesis of aminoglycoside antibiotics: cloning, expression and characterisation of an aminotransferase involved in the pathway to 2-deoxystreptamineElectronic supplementary information (ESI) available: LC-MS, TLC and ESI-Q-TOF MS. See http://www.rsc.org/suppdata/cc/b2/b209799k/
  作者：Fanglu Huang、Yanyan Li、Jinquan Yu、Jonathan B. Spencer

  DOI：10.1039/b209799k

  日期：2002.11.18

  Bacillus circulans has been cloned and expressed and shown to produce a protein which catalyses the transamination of 2-deoxy-scyllo-inosose to give 2-deoxy-scyllo-inosamine, an intermediate in the biosynthesis of 2-deoxystreptamine.

  已克隆并表达了来自圆形芽孢杆菌的基因btrR，并显示产生了一种蛋白质，该蛋白质催化2-脱氧-鞘氨醇的氨基转移，得到2-脱氧-鞘氨醇，其是2-脱氧链胺的生物合成的中间体。
• Characterization of l-glutamine:2-deoxy-scyllo-inosose aminotransferase (tbmB) from Streptomyces tenebrarius
  作者：Madan K. Kharel、Bimala Subba、Hei Chan Lee、Kwangkyoung Liou、Jae Kyung Sohng

  DOI：10.1016/j.bmcl.2004.10.028

  日期：2005.1

  2-Deoxystreptamine (DOS)-containing aminoglycoside-aminocyclitol (AmAc) antibiotics represent the majority of clinically important AmAcs. Biosynthetic investigations of formation of DOS in actinomycetes are limited to the characterization of 2-deoxy-scyllo-inosose synthase, the first step enzyme of the DOS biosynthetic pathway. A gene encoding L-glutamine:2-deoxy-scyllo-mosose aminotransferase (tbmB) from the tobramycin producer Streptomyces tenebrarius was expressed heterologously in Escherichia coli. The conversions of 2-deoxy-scyllo-inosose to 2-deoxy-scyllo-inosamine and scyllo-inosose to scyllo-inosamine with the activity of TbmB were determined in vitro. The results indicate that tbmB catalyzes the second step of the DOS biosynthetic pathway during the biosynthesis of 2-deoxystreptamine, a subunit of tobramycin, in S. tenebrarius. (C) 2004 Elsevier Ltd. All rights reserved.
• Chemical synthesis of 3-amino-2,3-dideoxy-d-myo-inositol (an intermediate in the biosynthesis of 2-deoxystreptamine) and its d-epi stereoisomer
  作者：Hans H. Baer、Lisa Siemsen、David J. Astles

  DOI：10.1016/s0008-6215(00)90119-8

  日期：1986.11
• Convenient synthesis of 2-deoxy-scyllo-inosose and 2-deoxy-scyllo-inosamine: two key intermediates on the biosynthetic pathway to aminoglycoside antibiotics
  作者：Jinquan Yu、Jonathan B Spencer

  DOI：10.1016/s0040-4039(01)00612-8

  日期：2001.6

  2-Deoxy-scyllo-inosose 1 and 2-deoxy-scyllo-inosamine 2 are two of the key intermediates on the biosynthetic pathway to 2-deoxystreptamine-containing aminoglycoside antibiotics. Convenient syntheses of 1, 2 and tritium-labelled 2 via stereoselective deoxygenation of myo-inositol using LTBH are reported. This should provide the substrates necessary for characterising the enzymes involved on the biosynthetic

  2-脱氧青蟹-inosose 1和2-脱氧青蟹-inosamine 2是含2脱氧链霉胺氨基糖苷类抗生素两个在生物合成途径中的关键中间体的对。的方便合成1，2和氚标记的2经由立体选择性脱氧肌使用LTBH肌醇报告。这应该提供表征生物合成途径所涉及的酶所必需的底物。