1-amino-1-deoxy-scyllo-inositol | 16051-25-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-amino-1-deoxy-scyllo-inositol
• 英文别名: scyllo-inosamine；6t-amino-cyclohexane-1r,2t,3c,4t,5c-pentaol；6t-Amino-cyclohexan-1r,2t,3c,4t,5c-pentaol；Inosamin-SB；6t-Amino-cyclohexanpentol-(1r.2t.3c.4t.5c)；1-Amino-1-desoxy-scyllo-inosit
• CAS: 16051-25-5
• 化学式: C₆H₁₃NO₅
• 分子量: 179.173
• InChiKey: JXAOTICXQLILTC-CDRYSYESSA-N

物化性质

• 沸点：
  334.4±42.0 °C(Predicted)
• 密度：
  1.810±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.87
• 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：
  1.0
• 拓扑面积：
  127.17
• 氢给体数：
  6.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-amino-1-deoxy-scyllo-inositol 在 sodium acetate 作用下， 生成 penta-O-acetyl-1-acetylamino-1-deoxy-scyllo-inositol
  参考文献：
  名称：

  Carter et al., Journal of Biological Chemistry, 1948, vol. 175, p. 683,688, 689

  摘要：

  DOI：
• 作为产物：
  描述：

  4,5,6-tri-O-benzyl-1,2-anhydro-myo-inositol 在 lithium aluminium tetrahydride 、 sodium azide 、 lithium perchlorate 、 三氯化硼 、 sodium hydride 作用下， 以 四氢呋喃 、 正庚烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 68.5h， 生成 1-amino-1-deoxy-scyllo-inositol
  参考文献：
  名称：

  New aminocyclitols as modulators of glucosylceramide metabolism

  摘要：

  一系列13种氨基环醇衍生物分属两个不同的家族。它们的构型由适当保护的顺-B-环氧环己烷醇开环反应的区域和立体控制决定。对几种糖基加工酶的研究表明，其中一些是葡萄糖基神经酰胺酶的良好抑制剂。提供了初步结构-活性关系的解释。

  DOI：

  10.1039/b411473f

文献信息

• New Glucocerebrosidase Inhibitors by Exploration of Chemical Diversity of <i>N</i>-Substituted Aminocyclitols Using Click Chemistry and in Situ Screening
  作者：Lucía Díaz、Josefina Casas、Jordi Bujons、Amadeu Llebaria、Antonio Delgado

  DOI：10.1021/jm101204u

  日期：2011.4.14

  the reaction can be carried out in an aqueous system, the resulting library members can be screened in situ with minimal manipulation. From the preliminary GCase inhibition data, the most potent library members have been individually resynthesized for further biological screening and complete characterization. Some of the library members have shown biochemical data (IC50, Ki, and stabilization ratio)

  从之间CuAAC反应衍生aminocyclitols的文库Ñ -propargylaminocyclitol 4和一系列叠氮化物[的1 - 25]进行了描述并针对GCase进行了测试。叠氮化物已从大量潜在候选物中选择，这些候选物已根据物理和反应性约束条件进行了过滤。为了避免使用氨基环糖醇支架上的保护基，已经优化了合成方法。由于该反应可以在水性体系中进行，因此可以通过最少的操作就地筛选所得的文库成员。从初步的GCase抑制数据来看，已经将最有效的文库成员单独重新合成以进行进一步的生物学筛选和完整表征。一些图书馆成员的生化数据（IC 50，K i和稳定比）与NNDNJ报告的相似或更好。。对接研究已用于假设配体-酶相互作用，以说明实验结果。
• 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。
• Small-Scale One-Pot Reductive Alkylation of Unprotected Aminocyclitols with Supported Reagents
  作者：Antonio Delgado、Miroslav Sisa、Ana Trapero、Amadeu Llebaria

  DOI：10.1055/s-2008-1067258

  日期：2008.10

  A protocol for the reductive alkylation of unprotected aminocyclitols with supported reagents and scavengers is described. The method is operatively simple and provides the corresponding secondary amines in high yields and purities.

  描述了使用支持的试剂和清除剂对未保护的氨基环醇进行还原烷基化的方案。该方法操作简单，并以高收率和纯度提供相应的仲胺。
• Stereochemical Recognition of Doubly Functional Aminotransferase in 2-Deoxystreptamine Biosynthesis
  作者：Kenichi Yokoyama、Fumitaka Kudo、Mieko Kuwahara、Kousuke Inomata、Hideyuki Tamegai、Tadashi Eguchi、Katsumi Kakinuma

  DOI：10.1021/ja0445948

  日期：2005.4.1

  The doubly functional aminotransferase BtrS in the 2-deoxystreptamine (DOS) biosynthesis, in which two transaminations are involved, was characterized by a genetic as well as a chemical approach with the heterologously expressed enzyme. The gene disruption study clearly showed that BtrS is involved, in addition to the previously confirmed first transamination, in the second transamination as well. This dual function of BtrS for the DOS biosynthesis was further confirmed by the structural determination of the reverse reaction product from DOS. Enantiospecific formation of the reverse reaction product from DOS clearly showed that BtrS distinguishes the enantiotopic amino groups of DOS, but in contrast, both enantiomers of 2-deoxy-scyllo-inosose (DOI) were efficiently accepted by BtrS to give a racemic product. This unique stereochemical recognition of DOI chirality and DOS prochirality by BtrS is mechanistically explained by a specific hydrogen-bond donating force in the enzyme active site as a particular feature of this doubly functional enzyme.
• 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.