1,3,2'-tri-N-(tert-butoxycarbonyl)neamine | 171366-87-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,2'-tri-N-(tert-butoxycarbonyl)neamine
• 英文别名: tert-butyl N-[(2R,3R,4R,5S,6R)-6-(aminomethyl)-2-[(1R,2R,3S,4R,6S)-2,3-dihydroxy-4,6-bis[(2-methylpropan-2-yl)oxycarbonylamino]cyclohexyl]oxy-4,5-dihydroxyoxan-3-yl]carbamate
• CAS: 171366-87-3
• 化学式: C₂₇H₅₀N₄O₁₂
• 分子量: 622.714
• InChiKey: AFBPCZGMTUJBNY-LNYKISQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  240
• 氢给体数：
  8
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  1,3,2'-tri-N-(tert-butoxycarbonyl)neamine 在 sodium tetrahydroborate 、 3 Angstroem MS 、 Amberlite IRA-400 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 21.0h， 生成
  参考文献：
  名称：

  Synthesis of neamine libraries for RNA recognition using solution phase chemistry

  摘要：

  Selective protection of the 6'-amino group of neamine allows the preparation of aminoglycoside libraries by reductive amination and Ugi multicomponent coupling. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01978-4
• 作为产物：
  描述：

  新霉素标液 在 盐酸 、 甲醇 、 sodium hydroxide 、 乙醇 、 溶剂黄146 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 100.5h， 生成 1,3,2'-tri-N-(tert-butoxycarbonyl)neamine
  参考文献：
  名称：

  Synthesis of neamine libraries for RNA recognition using solution phase chemistry

  摘要：

  Selective protection of the 6'-amino group of neamine allows the preparation of aminoglycoside libraries by reductive amination and Ugi multicomponent coupling. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01978-4

文献信息

• Synthesis of a Phosphonate-Linked Aminoglycoside-Coenzyme A Bisubstrate and Use in Mechanistic Studies of an Enzyme Involved in Aminoglycoside Resistance
  作者：Feng Gao、Xuxu Yan、Karine Auclair

  DOI：10.1002/chem.200802172

  日期：2009.2.16

  Just five steps! The synthesis of a phosphonate‐linked aminoglycoside‐coenzyme A derivative (see scheme) that includes a Michael addition in water has been realized in just five steps.

  只需五步！膦酸酯连接的氨基糖苷 - 辅酶 A 衍生物（见方案）的合成，包括在水中的迈克尔加成，仅用五个步骤就可以实现。
• Synthesis and use of sulfonamide-, sulfoxide-, or sulfone-containing aminoglycoside–CoA bisubstrates as mechanistic probes for aminoglycoside N-6′-acetyltransferase
  作者：Feng Gao、Xuxu Yan、Omar Zahr、Aaron Larsen、Kenward Vong、Karine Auclair

  DOI：10.1016/j.bmcl.2008.09.004

  日期：2008.10

  Aminoglycoside-coenzyme A conjugates are challenging synthetic targets because of the wealth of functional groups and high polarity of the starting materials. We previously reported a one-pot synthesis of amide-linked aminoglycoside-CoA bisubstrates. These molecules are nanomolar inhibitors of aminoglycoside N-6'-acetyltransferase Ii (AAC(6')-Ii), an important enzyme involved in bacterial resistance

  氨基糖苷-辅酶A共轭物因具有丰富的官能团和起始原料的高极性而成为具有挑战性的合成靶标。我们以前报道过一锅法合成酰胺连接的氨基糖苷-CoA双底物。这些分子是氨基糖苷N-6'-乙酰基转移酶Ii（AAC（6'）-Ii）的纳摩尔抑制剂，这是一种对细菌对氨基糖苷抗生素具有抗性的重要酶。我们在这里报告了五个新的包含磺酰胺，亚砜或砜基团的氨基糖苷-CoA双底物的合成和生物活性。有趣的是，与酰胺连接的双底物相比，预期最能模仿四面体中间体的磺酰胺连接的双底物没有显示出改善的抑制作用。另一方面，
• RNA targeting compounds and methods for making and using same
  申请人：The Research Foundation for The State University of New York

  公开号：US09260476B2

  公开（公告）日：2016-02-16

  Disclosed are RNA targeting compounds, methods for using the subject RNA targeting compounds to treat myotonic dystrophy and other diseases are also disclosed.

  本发明涉及RNA靶向化合物，还公开了使用该RNA靶向化合物治疗肌强直性萎缩症和其他疾病的方法。
• The use of neamine as a molecular template: Inactivation of bacterial antibiotic resistance enzyme aminoglycoside 3′-phosphotransferase type IIa
  作者：Juliatiek Roestamadji、Shahriar Mobashery

  DOI：10.1016/s0960-894x(98)00633-7

  日期：1998.12

  Aminoglycoside 3'-phosphotransferase type IIa [APH(3')-IIa] is a member of the family of bacterial aminoglycoside-modifying enzymes. Bacteria that harbor these enzymes are resistant to aminoglycoside antibiotics. Four aminoglycoside-based affinity inactivators were synthesized and were shown to be both substrates and inactivators for APH(3')-IIa. These affinity inactivators are N-bromoacetylated derivatives of neamine, an aminoglycoside antibiotic, where the bromoacetyl moiety in each was introduced regiospecifically at a different amine of the parent compound. (C) 1998 Elsevier Science Ltd. All rights reserved.