6-((6-biotinoylamino hexanoyl)aminohexanoyl)propargylamine | 226959-38-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 英文名称: 6-((6-biotinoylamino hexanoyl)aminohexanoyl)propargylamine
• 英文别名: biotinamidohexanoyl-6-aminohexanoyl propargylamide；6-((6-((Biotinoyl)amino)hexanoyl)amino)hexanoyl propargyl amine；6-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-N-[6-oxo-6-(prop-2-ynylamino)hexyl]hexanamide
• CAS: 226959-38-2
• 化学式: C₂₅H₄₁N₅O₄S
• 分子量: 507.698
• InChiKey: URPYUQKNOIOURL-SKPFHBQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  35
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  154
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-((6-biotinoylamino hexanoyl)aminohexanoyl)propargylamine 在 lithium hydroxide 、 copper(II) sulfate 、 sodium ascorbate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 25.0h， 生成 (Z)-2-Hydroxy-4-oxo-4-[3-(4-{4-[(6-{6-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoylamino}-hexanoylamino)-methyl]-[1,2,3]triazol-1-ylmethyl}-benzoyl)-phenyl]-but-2-enoic acid
  参考文献：
  名称：

  Biotinylated biphenyl ketone-containing 2,4-dioxobutanoic acids designed as HIV-1 integrase photoaffinity ligands

  摘要：

  The diketo acid (DKA) class of HIV-1 integrase inhibitors are thought to function by chelating divalent metal ions within the enzyme catalytic center. However, differences in mutations conferring resistance among sub-families of DKA inhibitors suggest that multiple binding orientations may exist. In order to facilitate identification of DKA-binding sites, biotin-tagged biphenyl ketone-containing 2,4-dioxobutanoic acids were prepared as DKA photoaffinity probes. Introduction of biotin was obtained by means of Huisgen [3+2] cycloaddition 'click chemistry.' Two photoprobes, 5a and 5b, were prepared bearing short and long linker segments, respectively, between the biotin and DKA nucleus. The greatest inhibitory potency was shown by 5b, which inhibited 3'-processing and strand transfer reactions with IC50 values of > 333 mu M and 12.4 mu M, respectively. In cross-linking assays designed to measure disruption of substrate DNA binding, the photoprobes behaved similarly to a reference DKA inhibitor. Analogues 5a and 5b represent novel photoaffinity ligands, which may be useful in clarifying the HIV-1 binding interactions of DKA inhibitors. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2006.07.064
• 作为产物：
  描述：

  联锡酰氨基己酰-6-氨基己酸N-羟基琥珀酰亚胺酯 、 炔丙胺 在 氯仿 、 正己烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.25h， 以A white precipitate formed within 15 min的产率得到6-((6-biotinoylamino hexanoyl)aminohexanoyl)propargylamine
  参考文献：
  名称：

  Methods of synthesis of halogen base-modified oligonucleotides and subsequent labeling with a metal-catalyzed reaction

  摘要：

  本发明提供了含金属的嘌呤、嘧啶、核苷、核苷酸和寡核苷酸，包括其磷酰胺酯和光致裂解衍生物，以及制备和使用它们的方法。本发明提供了一种通过电化学或光化学手段检测核酸序列的方法。

  公开号：

  US06288221B1

文献信息

• Palladium(0)-Catalyzed Modification of Oligonucleotides during Automated Solid-Phase Synthesis
  作者：Shoeb I. Khan、Mark W. Grinstaff

  DOI：10.1021/ja9836794

  日期：1999.5.1
• US6288221B1
  申请人：——

  公开号：US6288221B1

  公开（公告）日：2001-09-11