trimesoyl tris(3,5-dibromosalicylate) | 144181-06-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: trimesoyl tris(3,5-dibromosalicylate)
• 英文别名: trimesoyltris(3,5-dibromosalicylate)；2-[3,5-Bis[(2,4-dibromo-6-carboxyphenoxy)carbonyl]benzoyl]oxy-3,5-dibromobenzoic acid
• CAS: 144181-06-6
• 化学式: C₃₀H₁₂Br₆O₁₂
• 分子量: 1043.84
• InChiKey: YQZHDVJGAQJRRT-UHFFFAOYSA-N

物化性质

• 沸点：
  1077.7±65.0 °C(Predicted)
• 密度：
  2.200±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  48
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  191
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  trimesoyl tris(3,5-dibromosalicylate) 在 3-吗啉丙磺酸 作用下， 生成 Benzene-1,3,5-tricarboxylic acid bis-(2,4-dibromo-6-carboxy-phenyl) ester
  参考文献：
  名称：

  Trimesoyltris(3,5-dibromosalicylate): specificity of reactions of a trifunctional acylating agent with hemoglobin

  摘要：

  Trimesoyltris(3,5-dibromosalicylate)(TTDS) was prepared and evaluated as a trifunctional site-directed protein cross-linking reagent. It is synthesized by reaction of trimesoyl chloride with tert-butyl 3,5-dibromosalicylate, followed by deprotection with trifluoroacetic acid. TTDS reacts with the deoxy form of human hemoglobin A and with carbonmonoxyhemoglobin to produce amides from the epsilon-amino groups of Lys-82 of each of the beta chains of hemoglobin. The third 3,5-dibromosalicylate ester group from TTDS reacts much more slowly, principally undergoing hydrolysis. Minor products include materials with alpha-chain modification and triply linked trimesoyl (beta82Lys, beta1Val, beta'82Lys)hemoglobin. Comparison of these results with results from other reagents indicates that the nature of the leaving group and the structure of the acylating core control the observed specificity.

  DOI：

  10.1021/ja00050a005
• 作为产物：
  描述：

  1,3,5-苯三甲酰氯 在 potassium tert-butylate 、 三氟乙酸 作用下， 反应 1.25h， 生成 trimesoyl tris(3,5-dibromosalicylate)
  参考文献：
  名称：

  Trimesoyltris(3,5-dibromosalicylate): specificity of reactions of a trifunctional acylating agent with hemoglobin

  摘要：

  Trimesoyltris(3,5-dibromosalicylate)(TTDS) was prepared and evaluated as a trifunctional site-directed protein cross-linking reagent. It is synthesized by reaction of trimesoyl chloride with tert-butyl 3,5-dibromosalicylate, followed by deprotection with trifluoroacetic acid. TTDS reacts with the deoxy form of human hemoglobin A and with carbonmonoxyhemoglobin to produce amides from the epsilon-amino groups of Lys-82 of each of the beta chains of hemoglobin. The third 3,5-dibromosalicylate ester group from TTDS reacts much more slowly, principally undergoing hydrolysis. Minor products include materials with alpha-chain modification and triply linked trimesoyl (beta82Lys, beta1Val, beta'82Lys)hemoglobin. Comparison of these results with results from other reagents indicates that the nature of the leaving group and the structure of the acylating core control the observed specificity.

  DOI：

  10.1021/ja00050a005

文献信息

• Mechanism of Site-Directed Protein Cross-Linking. Protein-Directed Selectivity in Reactions of Hemoglobin with Aryl Trimesates
  作者：Ronald Kluger、Vittorio De Stefano

  DOI：10.1021/jo991514n

  日期：2000.1.1

  Site-directed cross-linking of hemoglobin has become an efficient way to produce a structurally defined altered protein with desirable functional properties. The reagent trimesoyl tris(3,5-dibromosalicylate) (1) introduces a bis amide cross-link derived from the epsilon-amino groups of the side chains of the two beta-Lys-82 residues in human hemoglobin. The basis of its specificity was investigated using a set of analogues of 1 (2-12). There are marked differences in the reaction patterns of these compounds with amino groups in hemoglobin compared to reactions with n-propylamine. The compounds that effectively modify the protein contain a carboxyl group ortho to the phenolic oxygen of the ester, while materials with meta or para carboxyl groups give little or no reaction. In contrast, the reactions with n-propylamine are slowest with the ortho carboxyl materials. Addition of the unreactive compound 5 to a solution containing hemoglobin reduces the ability of 1 to modify the protein, showing that the unreactive compound binds but does not react. On the basis of these observations and the known reaction patterns of salicylates, it is clear that: the environment in the protein controls the reaction, regardless of the inherent reactivity of the reagent. We propose that the carboxyl group positions the reagent critically within the protein. Only the ortho arrangement permits transfer of the acyl function to the nucleophile.
• SPECIFICALLY CROSSLINKED HEMOGLOBIN WITH FREE FUNCTIONALITY
  申请人：THE UNIVERSITY OF TORONTO INNOVATIONS FOUNDATION

  公开号：EP0669940B1

  公开（公告）日：1999-02-10
• [EN] STABILIZED HEMOGLOBIN-AVIDIN ASSEMBLY AND METHOD OF PREPARATION<br/>[FR] ENSEMBLE HÉMOGLOBINE-AVIDINE STABILISÉ ET PROCÉDÉ DE PRÉPARATION
  申请人：GOVERNING COUNCIL UNIV TORONTO

  公开号：WO2017197499A1

  公开（公告）日：2017-11-23

  The disclosure concerns a hemoglobin based oxygen carrier (HBOC) comprising avidin or streptavidin and a hemoglobin conjugate preferably comprising a conjugate of hemoglobin and biotin where the conjugate is associated with avidin. The HBOC is capable of binding oxygen and releasing same in circulation in animals or humans. The design of the HBOC is intended so that it would not be vasoactive in vivo. The disclosure also concerns a method of synthesis and a method of use, or the use, of the HBOC for providing oxygen transport in the circulatory system of a human or animal.
• [EN] HEMOGLOBIN BASED OXYGEN CARRIER AND METHOD OF PREPARATION<br/>[FR] PORTEUR D'OXYGÈNE À BASE D'HÉMOGLOBINE ET PROCÉDÉ DE PRÉPARATION
  申请人：GOVERNING COUNCIL UNIV TORONTO

  公开号：WO2018053634A1

  公开（公告）日：2018-03-29

  The disclosure concerns a class of hemoglobin based oxygen carriers (HBOCs) comprising a first hemoglobin protein cross-linked by a chemical reaction that is followed by a strain-promoted alkyne-azide cycloaddition (SPAAC) reaction or by a strain-promoted alkyne-nitrone cycloaddition (SPANC) in the absence of added copper salts to a second modified cross-linked hemoglobin protein. The resulting construct is an HBOC that is capable of binding oxygen and releasing same in a useful manner upon addition in an appropriate solution to the circulatory system of a patient. The disclosure also concerns a method of production of the HBOC where a first and second hemoglobin protein are produced by covalently linking hemoglobin to an angle strained cycloalkyne moiety. A compound comprising at least 2 azide or nitrone moieties is then added for reacting under conditions conducive to SPAAC or SPANC reaction in absence of copper ions with the first and second hemoglobin protein for causing covalent linkage of the first and second hemoglobin protein to the compound comprising said at least 2 azide or nitrone moieties, resulting in said HBOC. The HBOC can be used for transfusion, perfusion or for increasing oxygen transport.
• Trimesoyltris(3,5-dibromosalicylate): specificity of reactions of a trifunctional acylating agent with hemoglobin
  作者：Ronald Kluger、Yonghong Song、Jolanta Wodzinska、Charlotte Head、Thomas S. Fujita、Richard T. Jones

  DOI：10.1021/ja00050a005

  日期：1992.11

  Trimesoyltris(3,5-dibromosalicylate)(TTDS) was prepared and evaluated as a trifunctional site-directed protein cross-linking reagent. It is synthesized by reaction of trimesoyl chloride with tert-butyl 3,5-dibromosalicylate, followed by deprotection with trifluoroacetic acid. TTDS reacts with the deoxy form of human hemoglobin A and with carbonmonoxyhemoglobin to produce amides from the epsilon-amino groups of Lys-82 of each of the beta chains of hemoglobin. The third 3,5-dibromosalicylate ester group from TTDS reacts much more slowly, principally undergoing hydrolysis. Minor products include materials with alpha-chain modification and triply linked trimesoyl (beta82Lys, beta1Val, beta'82Lys)hemoglobin. Comparison of these results with results from other reagents indicates that the nature of the leaving group and the structure of the acylating core control the observed specificity.