4-[6-(biotinylamino)hexanoylamino]butyl 2-(dimethylamino)acetate | 1260379-66-5

• 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: 4-[6-(biotinylamino)hexanoylamino]butyl 2-(dimethylamino)acetate
• 英文别名: 4-[6-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]hexanoylamino]butyl 2-(dimethylamino)acetate
• CAS: 1260379-66-5
• 化学式: C₂₄H₄₃N₅O₅S
• 分子量: 513.702
• InChiKey: BLAHYTNPLYBDLQ-YDHSSHFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  35
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  154
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-aminobutyl N,N-dimethylglycine bis(trifluoroacetate) 、 N-生物素己酸 在 N-甲基吗啉 、 4-(4,6-二甲氧基三嗪-2-基)-4-甲基吗啉盐酸盐 作用下， 以 甲醇 为溶剂， 以46%的产率得到4-[6-(biotinylamino)hexanoylamino]butyl 2-(dimethylamino)acetate
  参考文献：
  名称：

  Labeling study of avidin by modular method for affinity labeling (MoAL)

  摘要：

  We studied the specific labeling of avidin with biotinylated modular ligand catalysts via MoAL, which we recently established. The labeling yield was found to depend on the linker length connecting the catalytic site to biotin in the modular ligand catalyst 1, and the maximum yield was obtained with 1d possessing octamethylene linker. The labeling reaction reached a maximum rate with only 4 equiv of the ligand catalyst. Presumably, all the subunits of avidin with homotetrameric structure formed a stable complex with 4 equiv of the catalyst because of the extremely high affinity. The ligand catalyst bound to avidin first catalyzed N-triazinylation of the e-amino group of Lys111, and the resulting regenerated catalyst then catalyzed the reaction of Asp108 and CDMT. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.109

文献信息

• Labeling study of avidin by modular method for affinity labeling (MoAL)
  作者：Shuichi Nakanishi、Hiroyuki Tanaka、Kazuhito Hioki、Kohei Yamada、Munetaka Kunishima

  DOI：10.1016/j.bmcl.2010.09.109

  日期：2010.12

  We studied the specific labeling of avidin with biotinylated modular ligand catalysts via MoAL, which we recently established. The labeling yield was found to depend on the linker length connecting the catalytic site to biotin in the modular ligand catalyst 1, and the maximum yield was obtained with 1d possessing octamethylene linker. The labeling reaction reached a maximum rate with only 4 equiv of the ligand catalyst. Presumably, all the subunits of avidin with homotetrameric structure formed a stable complex with 4 equiv of the catalyst because of the extremely high affinity. The ligand catalyst bound to avidin first catalyzed N-triazinylation of the e-amino group of Lys111, and the resulting regenerated catalyst then catalyzed the reaction of Asp108 and CDMT. (C) 2010 Elsevier Ltd. All rights reserved.