bromoacetylglycine | 56674-21-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: bromoacetylglycine
• 英文别名: N-bromoacetyl-glycine；N-Bromacetyl-glycin；Bromacetamino-essigsaeure；N-Bromacetylglycin；Bromacetylglycin；N-(Bromoacetyl)glycine；2-[(2-bromoacetyl)amino]acetic acid
• CAS: 56674-21-6
• 化学式: C₄H₆BrNO₃
• 分子量: 196.001
• InChiKey: VDMYKLFYXRGJKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  bromoacetylglycine 、 乙二胺-N,N’-二乙酸 在 sodium hydroxide 作用下， 生成 2-[[2-[Carboxymethyl-[2-[carboxymethyl-[2-(carboxymethylamino)-2-oxoethyl]amino]ethyl]amino]acetyl]amino]acetic acid
  参考文献：
  名称：

  New multidentate ligands. X. Chelating tendencies of N,N'-diglycylethylenediamine-N'',N'',N''',N'''-tetraacetic acid and ethylenediamine-N-N'-di(acetylglycine)-N,N'-diacetic acid

  摘要：

  DOI：

  10.1021/ja00717a016
• 作为产物：
  描述：

  溴乙酰氯 、 聚甘氨酸 在 aq. base 作用下， 生成 bromoacetylglycine
  参考文献：
  名称：

  Synthesis, labelling and biological characteristics of derivatives of Mercaptoacetyltriglycine with two amide functions

  摘要：

  我们合成并评估了八种新型 MAG3 衍生物，它们的结构中含有两个而非三个酰胺功能。合成的配体在 100°C 下通过交换标记法和/或室温下通过直接标记法进行 99mTc 标记。用 99mTc 标记后，用放射性-高效液相色谱法对反应混合物进行分析。在小鼠和狒狒体内对不同的 99mTc 二酰胺复合物进行的生物学评估表明，MAG3 结构中一个酰胺功能的取代极大地影响了这些化合物的肾脏处理能力。研究发现，至少含有一个倒置酰胺的二酰胺衍生物具有与 99mTc-MAG3 相似的生物学行为。Copyright © 2002 John Wiley & Sons, Ltd. All Rights Reserved.

  DOI：

  10.1002/jlcr.538

文献信息

• Controlled coupling of aminoglycoside antibiotics to proteins for use in homogeneous enzyme immunoassays
  作者：Prithipal Singh、Marcel Pirio、Danton K. Leung、Yuh-Geng Tsay

  DOI：10.1139/v84-425

  日期：1984.11.1

  Selective N-acylation of aminoglycoside antibiotics with the N-hydroxysuccinimide ester of methyldithioacetic acid, followed by reaction with methanethiol or dithioerythritol, gives sulfhydryl labeled antibiotics. Alternatively, the nucleophilic sulfhydryl group is incorporated into an antibiotic by treatment with N-acetyl-d,l-homocysteine thiolactone. These derivatives couple readily with proteins that have previously been modified with bromoacetylglycyl groups to provide conjugates for use in the development of homogeneous enzyme immunoassays.

  氨基糖苷抗生素的选择性N-酰化，使用甲基二硫乙酸的N-羟基琥珀酰亚胺酯，随后与甲硫醇或二硫巴比妥醇反应，可制备含硫巯基标记的抗生素。或者，通过与N-乙酰-d,l-同型半胱氨酸硫内酯处理，将亲核硫巯基基团引入抗生素中。这些衍生物可与之前用溴乙酰甘氨酰基修饰过的蛋白质轻松偶联，用于开发均相酶免疫分析的共轭物。
• New heterobifunctional cross-linking reagents for protein conjugation, N-(bromoacetamido-n-alkanoyloxy)succinimides.
  作者：KIYOSHI ZAITSU、MIKIO OHNISHI、HIROYUKI HOSOYA、HIROYUKI SUGIMOTO、YOSUKE OHKURA

  DOI：10.1248/cpb.35.1991

  日期：——

  Five heterobifunctional reagents, N- (bromoacetamido-n-alkanoyloxy) succinimides having a glycine or ω-amino acid (β-alanine, γ-aminobutyric acid, δ-aminovaleric acid or ε-aminocaproic acid) residue, were synthesized. Bromoacetamido-n-alkanoyl groups could be introduced into horseradish peroxidase and hen egg-white lysozyme and its reduced and S-3- (trimethylated amino) propylated product by using the reagents. The number of bromoacetamido-n-alkanoyl groups introduced into the proteins could be successfully estimated from the amount of glycine or ω-amino acid (non-protein amino acid) produced from the introduced groups by acid hydrolysis. N- (β-Bromoacetamido-n-propionoyloxy) succinimide, one of the reagents, was examined as a reagent for the preparation of horseradish peroxidase-insulin conjugate. A single β-bromoacet- amido-n-propionoyl group was first introduced into GlyA1, PheB1-dicitraconylinsulin through the ε-amino group of its LysineB29 residue and the product was subjected to decitraconylation with dilute acetic acid to obtain LysB29- (β-bromoacetamido-n-propionoyl) insulin. The insulin was reacted with thiolated horseradish peroxidase to give peroxidase-insulin conjugate (molar ratio of 1 : 1).

  合成了五种含有甘氨酸或ω-氨基酸(β-丙氨酸、γ-氨基丁酸、δ-氨基戊酸或ε-氨基己酸)残基的杂双功能试剂N-(溴乙酰胺-n-烷酰氧基)琥珀酰亚胺。使用这些试剂可以将溴乙酰胺-n-烷酰基引入辣根过氧化物酶、蛋白蛋白酶及其还原和S-3-(三甲基化氨基)丙基化产物中。通过酸水解所引入基团产生的甘氨酸或ω-氨基酸(非蛋白氨基酸)的量,可以成功估算蛋白质中引入的溴乙酰胺-n-烷酰基的数量。其中一种试剂N-(β-溴乙酰胺-n-丙酰氧基)琥珀酰亚胺被研究用作制备辣根过氧化物酶-胰岛素结合物的试剂。首先通过赖氨酸B29残基的ε-氨基将单个β-溴乙酰胺-n-丙酰基引入GlyA1、PheB1-二柠檬酰胰岛素中,然后用稀醋酸使产物去柠檬酰化,得到LysB29-(β-溴乙酰胺-n-丙酰基)胰岛素。该胰岛素与硫化辣根过氧化物酶反应,得到过氧化物酶-胰岛素结合物(摩尔比为1:1)。
• Modulation of the Lifetime of Water Bound to Lanthanide Metal Ions in Complexes with Ligands Derived from 1,4,7,10-Tetraazacyclododecane Tetraacetate (DOTA)
  作者：Shanrong Zhang、Xiuyan Jiang、A. Dean Sherry

  DOI：10.1002/hlca.200590086

  日期：2005.5

  tetraamide derivatives of DOTA were synthesized, and their lanthanide(III) complexes were examined by multinuclear 1H-, 13C-, and 17O-NMR spectroscopy, and compared with literature data of similar, known complexes (Table). All ligands formed structures similar to the parent [LnIII(DOTA)]− complexes, with four N-atoms and four O-atoms from DOTA and one O-atom from the inner-sphere water molecules. Interestingly

  合成了一系列DOTA的二酰胺和四酰胺衍生物，并通过多核1 H-，13 C-和17 O-NMR光谱检查了它们的镧系元素（III）配合物，并与相似的已知配合物的文献数据进行了比较（表）。所有配体形成类似于母体[Ln III（DOTA）] -配合物的结构，其中DOTA带有四个N原子和四个O原子，内圈水分子带有一个O原子。有趣的是，寿命τ中号的内球面的，金属结合的水分子广泛地变化，范围从纳米到毫秒，这取决于悬垂酰胺侧链的身份。通常，带正电的[LnIII（DOTA-四酰胺）] 3+络合物显示最长的停留时间（高τ中号的值），而在扩展酰胺与另外的带电官能团的复合物显示小得多的τ中号值，即使当侧基不直接协调，以中心的Ln 3+离子。新颖的设计[LN III（DOTA-四酰胺）] 3+配合物的宽，调谐范围τ中号值是最重要的用于快速响应的，顺磁性化学交换饱和转移（PARACEST）成像的应用用于研究生理和代谢过程的药物。
• Method for conjugating to polyamino compounds employing haloacyl groups
  申请人：Syva Company

  公开号：US04220722A1

  公开（公告）日：1980-09-02

  Methods and compositions are provided for conjugating a wide variety of compounds, particularly polyfunctional compounds, having a mercapto group, either naturally present or synthetically introduced, to a polyamino compound, particularly a polypeptide (including proteins). The method employs a haloalkylcarbonyl compound, which is conjugated to one or more of the amino groups under mild acylating conditions. This is followed by combining the acylated polyamino compound with a mercapto containing compound, whereby the halogen is displaced by the sulfur of the mercapto group to form a stable thioether linkage. The resulting conjugates, depending on the compounds involved, can find uses in immunoassays, as hapten-antigen conjugates for the production of antibodies, and as ligand analog enzyme conjugates for use as reagents in controlling the distribution of substitution of a mercapto compound to a polyamino compound.

  本发明提供了一种用于连接多种化合物的方法和组合物，特别是具有巯基的多功能化合物，其天然存在或合成引入，到多氨基化合物，特别是多肽（包括蛋白质）。该方法采用卤代烷基羰基化合物，在温和的酰化条件下与一个或多个氨基基团结合。然后将酰化的多氨基化合物与含有巯基的化合物结合，卤素被巯基的硫所取代，形成稳定的硫醚键。根据所涉及的化合物，所得到的共轭物可以在免疫测定中使用，作为半抗原-抗原共轭物用于抗体的生产，并作为配体类似物酶共轭物用于控制巯基化合物对多氨基化合物的取代分布的试剂。
• Enzyme-aminoglycoside conjugates
  申请人：Syva Company

  公开号：US04328311A1

  公开（公告）日：1982-05-04

  Methods and compositions are provided for conjugating a wide variety of compounds, particularly polyfunctional compounds, having a mercapto group, either naturally present or synthetically introduced, to a polyamino compound, particularly a polypeptide (including proteins). The method employs a haloalkyl-carbonyl compound, which is conjugated to one or more of the amino groups under mild acylating conditions. This is followed by combining the acylated polyamino compound with a mercapto containing compound, whereby the halogen is displaced by the sulfur of the mercapto group to form a stable thioether linkage. The resulting conjugates, depending on the compounds involved, can find uses in immunoassays, as hapten-antigen conjugates for the production of antibodies, and as ligand analog enzyme conjugates for use as reagents in controlling the distribution of substitution of a mercapto compound to a polyamino compound.

  本文提供了一种方法和组合物，用于将具有巨大作用的化合物，特别是具有巯基的多功能化合物，无论是自然存在还是合成引入，与多氨基化合物（特别是多肽，包括蛋白质）共轭。该方法采用卤代烷基-羰基化合物，在温和的酰化条件下与一个或多个氨基基团共轭。然后将酰化的多氨基化合物与含有巯基的化合物结合，从而使卤素被巯基的硫代替，形成稳定的硫醚连接。根据所涉及的化合物，所得到的共轭物可以在免疫测定中找到用途，作为半抗原-抗原共轭物用于抗体的生产，以及作为配体类似物酶共轭物用作试剂，以控制巯基化合物对多氨基化合物的取代分布。