N-6-(t-butoxycarbonylamino)hexyl 3-(2-hydroxyphenyl)propionamide | 268544-19-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-6-(t-butoxycarbonylamino)hexyl 3-(2-hydroxyphenyl)propionamide
• 英文别名: tert-butyl N-[6-[3-(2-hydroxyphenyl)propanoylamino]hexyl]carbamate
• CAS: 268544-19-0
• 化学式: C₂₀H₃₂N₂O₄
• 分子量: 364.485
• InChiKey: PGGHTHJVMPPMII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  26
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-6-(t-butoxycarbonylamino)hexyl 3-(2-hydroxyphenyl)propionamide 在 盐酸 、 氢氧化钾 、 TEA 、 sodium nitrite 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 1.58h， 生成 3'-(6-(succinimidyloxycarbonylamino)hehylaminocarbonylethyl)-4'-hydroxy-azobenzene-2-carboxylic acid
  参考文献：
  名称：

  A Chemical Approach To Illustrate the Principle of Signal Transduction Cascades Using the Avidin−Biotin System

  摘要：

  A new approach to illustrate the principle of signal transduction and to assemble protein multilayers is described. It is based on competing affinities of two different ligands for the same binding site of a protein. A low-affinity ligand can be attached covalently to the protein, where it will be buried in the binding site and thus be prevented to interact with other proteins that recognize it. However, if a high-affinity ligand (or a molecule containing this ligand) is added, it will displace the low-affinity ligand (which still remains covalently bound) from the binding site to the periphery. The low-affinity ligand is now available for interaction with other molecules, thus providing the means through which to assemble multilayers of proteins by a "recognition cascade". This principle was demonstrated using the protein avidin which binds two ligands, biotin and 4-hydroxyazobenzene-2-carboxylic acid (HABA), with markedly different affinities. Avidin was affinity labeled with HABA, the low-affinity ligand, to produce a red, covalently conjugated avidin-HABA derivative (red avidin). Anti-HABA antibodies failed to recognize HABA buried in the binding site of avidin. However, upon addition of the high-affinity ligand biotin, HABA was expelled from the binding site and immediately bound by the antibodies. Multilayer assemblies of HABAylated avidin and biotinylated anti-HABA antibodies could thus be constructed. This concept may find application in numerous fields, such as medicine, diagnostics, nanotechnology, and artificial intelligence.

  DOI：

  10.1021/ja982817m
• 作为产物：
  描述：

  3-(2-羟基苯基)丙酸 在 TEA 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 N-6-(t-butoxycarbonylamino)hexyl 3-(2-hydroxyphenyl)propionamide
  参考文献：
  名称：

  A Chemical Approach To Illustrate the Principle of Signal Transduction Cascades Using the Avidin−Biotin System

  摘要：

  A new approach to illustrate the principle of signal transduction and to assemble protein multilayers is described. It is based on competing affinities of two different ligands for the same binding site of a protein. A low-affinity ligand can be attached covalently to the protein, where it will be buried in the binding site and thus be prevented to interact with other proteins that recognize it. However, if a high-affinity ligand (or a molecule containing this ligand) is added, it will displace the low-affinity ligand (which still remains covalently bound) from the binding site to the periphery. The low-affinity ligand is now available for interaction with other molecules, thus providing the means through which to assemble multilayers of proteins by a "recognition cascade". This principle was demonstrated using the protein avidin which binds two ligands, biotin and 4-hydroxyazobenzene-2-carboxylic acid (HABA), with markedly different affinities. Avidin was affinity labeled with HABA, the low-affinity ligand, to produce a red, covalently conjugated avidin-HABA derivative (red avidin). Anti-HABA antibodies failed to recognize HABA buried in the binding site of avidin. However, upon addition of the high-affinity ligand biotin, HABA was expelled from the binding site and immediately bound by the antibodies. Multilayer assemblies of HABAylated avidin and biotinylated anti-HABA antibodies could thus be constructed. This concept may find application in numerous fields, such as medicine, diagnostics, nanotechnology, and artificial intelligence.

  DOI：

  10.1021/ja982817m

文献信息

• Avidin derivatives and uses thereof
  申请人：YEDA RESEARCH AND DEVELOPMENT CO., LTD.

  公开号：US20040191832A1

  公开（公告）日：2004-09-30

  A covalent conjugate of a 4′-hydroxyazobenzene-2-carboxylic acid. derivative (HABA) and an avidin-type molecule, of the formula: 1 wherein A is (CH 2 ) n or —CH═CH—, wherein n is an integer from 0-10; B is (CH 2 ) n wherein n is an integer from 2 to 10; m is zero or 1; and Av is the residue of an avidin-type molecule selected from the group comprising native egg-white avidin, recombinant avidin, deglycosylated avidins, bacterial streptavidin, recombinant streptavidin, truncated streptavidin and other derivatives of said avidin-type molecules. These HABAylated avidins are red colored in the quinone configuration and can be used in many applications in the avidin-biotin technology.

  4′-hydroxyazobenzene-2-carboxylic acid.衍生物（HABA）与阿维丁类分子的共价共轭物，其分子式为 1 其中 A 是（CH 2 ) n 或-CH═CH-，其中 n 是 0-10 之间的整数； B 是 (CH 2 ) n 或-CH═CH-，其中 n 是 0-10 之间的整数。 2 ) n 其中 n 是 2-10 之间的整数；m 是 0 或 1；Av 是选自下列组的阿维丁类分子的残基：原生蛋清阿维丁、重组阿维丁、脱糖阿维丁、细菌链霉亲和素、重组链霉亲和素、截短链霉亲和素和上述阿维丁类分子的其他衍生物。这些 HABAylated avidins 在醌构型中呈红色，可用于 avidin 生物素技术的多种应用中。
• Azobenzene derivatives as labeling agents and intermediates thereof
  申请人：Yeda Research and Development Co. Ltd.

  公开号：US20040067229A1

  公开（公告）日：2004-04-08

  A compound of the formula I 1 wherein R is H or —N═N-2-carboxyphenyl; A is (CH 2 ) n or —CH═CH—, wherein n is an integer from 0 to 10, or A may also be —CH(COOH)— when R is —N═N-2-carboxyphenyl; and X is a radical selected from the group consisting of: (i) Cl; (ii) COOR 1 , wherein R 1 is p-nitrophenyl or N-succinimidyl; (iii) CONH—NHR 2 , wherein R 2 is H, COO(t-butyl) or COObenzyl; (iv) CONH—[B]—NHR 3 , wherein R 3 is H, COOR 1 , or CO-[B′]-maleimido, wherein R 1 is t-butyl, p-nitrophenyl or N-succinimidyl, and B and B′, the same or different, are (CH 2 ) n wherein n is an integer from 2 to 10; (v) CONH—[B]—COOR 4 , wherein R 4 is H, C 1 -C 8 alkyl, N-succinimidyl; (vi) CONH—[B]—OH; (vii) CONH—[B]—CONH—NHR 2 , wherein R 2 is H, COO(t-butyl) or COObenzyl; and (viii) NHR 2 , wherein R 2 is H, COO(t-butyl) or COObenzyl, when A is —CH(COOH)— and R is —N═N-2-carboxyphenyl. The 4′-hydroxyazobenzene-2-carboxylic acid (HABA) compounds are novel reagents for labeling, isolation and detection of biological molecules.
• US6602987B1
  申请人：——

  公开号：US6602987B1

  公开（公告）日：2003-08-05
• US6632929B1
  申请人：——

  公开号：US6632929B1

  公开（公告）日：2003-10-14
• US7217575B2
  申请人：——

  公开号：US7217575B2

  公开（公告）日：2007-05-15