allyl 2-amino-6-azido-2,6-dideoxy-α-D-glucopyranoside | 213528-66-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2-amino-6-azido-2,6-dideoxy-α-D-glucopyranoside
• 英文别名: (2R,3S,4R,5R,6S)-5-amino-2-(azidomethyl)-6-prop-2-enoxyoxane-3,4-diol
• CAS: 213528-66-6
• 化学式: C₉H₁₆N₄O₄
• 分子量: 244.25
• InChiKey: ZRZNLFWAYHVXNV-OKNNCHMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  99.3
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  allyl 2-amino-6-azido-2,6-dideoxy-α-D-glucopyranoside 在 二甲基硫 、 sodium cyanoborohydride 、 臭氧 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  A Library Approach to the Discovery of Small Molecules That Recognize RNA:  Use of a 1,3-Hydroxyamine Motif as Core

  摘要：

  A library of compounds based upon an aminoglucopyranoside core has been developed and screened for binding to RNA and specifically to 16S ribosomal RNA. The title molecules simplify the complexity of naturally occurring aminoglycoside antibiotics by embodying a putative recognition motif found within these structures, namely, a 1,3-hydroxyamine. The core pyranoside bearing the hydroxyamine motif was structurally varied at two points through a combinatorial approach utilizing acylation and reductive amination protocols. The aminoglycoside mimetics were screened in an automated assay based upon surface plasmon resonance (SPR), and some were found effective at binding a 27-nucleotide model (AS-wt) of A-site 16S RNA as well as a drug-resistant mutant RNA in the micromolar range.

  DOI：

  10.1021/ja980826p
• 作为产物：
  描述：

  allyl 2-acetamido-6-azido-2,6-dideoxy-α-D-glucopyranoside 在 barium hydroxide octahydrate 作用下， 以 水 为溶剂， 以78%的产率得到allyl 2-amino-6-azido-2,6-dideoxy-α-D-glucopyranoside
  参考文献：
  名称：

  新型抗耐药细菌的广谱抗菌两亲氨基糖苷：从神经胺衍生物到较小的新胺类似物

  摘要：

  氨基糖苷类（AGs）构成了主要的强效和广谱抗生素家族，它们通过与16S rRNA的A位点结合而干扰蛋白质的合成。几十年来，AGs的广泛临床应用通过选择耐药细菌而大大降低了其临床功效。最近，亲脂性基团与AGs的结合产生了一类新型的强效抗菌两亲氨基糖苷（AAG），其对各种敏感和耐药细菌菌株的活性均得到显着改善。我们已经确定了小氨基糖苷神经酰胺的两亲性3'，6-二烷基衍生物是靶向细菌膜的广谱抗菌剂。在这里，我们报道了新型两亲性3'对敏感和耐药革兰氏阴性和/或革兰氏阳性细菌的合成及其活性，N-乙酰氨基葡萄糖。

  DOI：

  10.1021/acs.jmedchem.6b00818

文献信息

• Synthesis of Amino-Bridged Oligosaccharide Mimetics
  作者：Janna Neumann、Joachim Thiem

  DOI：10.1002/ejoc.200901106

  日期：2010.2

  Synthesis of amino-bridged oligosaccharides using reductive amination opens rapid access to novel glycomimetic target structures as potential ligands for the receptor protein NKR P1 of natural killer cells. Emphasis was laid on fast and facile synthetic routes. The carbonyl building blocks were easily obtained by oxidation with Dess-Martin periodinane or iodoxybenzoic acid (IBX). For the required

  使用还原胺化合成氨基桥连寡糖开辟了快速获取新的拟糖靶结构作为自然杀伤细胞受体蛋白 NKR P1 的潜在配体的途径。重点放在快速简便的合成路线上。通过用戴斯-马丁高碘烷或碘氧基苯甲酸 (IBX) 氧化很容易获得羰基结构单元。对于所需的氨基官能化单元，叠氮化物前体的还原是有利的，并且通过随后的还原胺化实现了新型寡糖的生成。目标糖类结构的特征是在两个非异头位置之间插入一个桥接氮原子，并包括一个异头位置。
• Synthesis of linked carbohydrates and evaluation of Their binding for 16S RNA by mass spectrometry
  作者：Baogen Wu、Jun Yang、Dale Robinson、Steve Hofstadler、Rich Griffey、Eric E. Swayze、Yun He

  DOI：10.1016/j.bmcl.2003.09.005

  日期：2003.11

  A library of linked molecules were synthesized from the common sugar moieties existing in the natural amino glycosides. These linked molecules were screened against bacterial 16S RNA for their binding affinity using a mass spectrometry-based technology. Some of these compounds exhibited low micromolar affinity and could serve as leads for further development as antibacterial agents. (C) 2003 Published by Elsevier Ltd.