((S)-5-Amino-1-{(2S,3R,4R,5S,6R)-6-azidomethyl-2-[2-(2-benzyloxycarbonylamino-ethylamino)-ethoxy]-4,5-dihydroxy-tetrahydro-pyran-3-ylcarbamoyl}-pentyl)-carbamic acid benzyl ester | 213528-88-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ((S)-5-Amino-1-{(2S,3R,4R,5S,6R)-6-azidomethyl-2-[2-(2-benzyloxycarbonylamino-ethylamino)-ethoxy]-4,5-dihydroxy-tetrahydro-pyran-3-ylcarbamoyl}-pentyl)-carbamic acid benzyl ester
• CAS: 213528-88-2
• 化学式: C₃₂H₄₆N₈O₉
• 分子量: 686.765
• InChiKey: IHYSEKHMSWGSQJ-IOTUKHIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.18
• 重原子数：
  49.0
• 可旋转键数：
  20.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  251.49
• 氢给体数：
  7.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  ((S)-5-Amino-1-{(2S,3R,4R,5S,6R)-6-azidomethyl-2-[2-(2-benzyloxycarbonylamino-ethylamino)-ethoxy]-4,5-dihydroxy-tetrahydro-pyran-3-ylcarbamoyl}-pentyl)-carbamic acid benzyl ester 在 palladium dihydroxide 氢气 、 溶剂黄146 作用下， 生成 (2S)-2,6-diamino-N-[(2S,3R,4R,5S,6R)-2-[2-(2-aminoethylamino)ethoxy]-6-(aminomethyl)-4,5-dihydroxyoxan-3-yl]hexanamide
  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：

  [(S)-1-((2S,3R,4R,5S,6R)-2-Allyloxy-6-azidomethyl-4,5-dihydroxy-tetrahydro-pyran-3-ylcarbamoyl)-5-amino-pentyl]-carbamic acid benzyl ester 在 二甲基硫 、 sodium cyanoborohydride 、 臭氧 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 ((S)-5-Amino-1-{(2S,3R,4R,5S,6R)-6-azidomethyl-2-[2-(2-benzyloxycarbonylamino-ethylamino)-ethoxy]-4,5-dihydroxy-tetrahydro-pyran-3-ylcarbamoyl}-pentyl)-carbamic acid benzyl ester
  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