chloroacetyl-coenzyme A

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: chloroacetyl-coenzyme A
• 英文别名: chloroacetylcoenzyme A；S-[2-[3-[[(2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] 2-chloroethanethioate
• 化学式: C₂₃H₃₇ClN₇O₁₇P₃S
• 分子量: 844.024
• InChiKey: ILZFPFRGASSOTJ-GRFIIANRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5
• 重原子数：
  52
• 可旋转键数：
  21
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  389
• 氢给体数：
  9
• 氢受体数：
  22

反应信息

• 作为产物：
  描述：

  氯乙酸酐 、 辅酶 A 在 三乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.83h， 生成 chloroacetyl-coenzyme A
  参考文献：
  名称：

  Activity-Based Substrate Profiling for Gcn5-Related N-Acetyltransferases:  The Use of Chloroacetyl-Coenzyme A To Identify Protein Substrates

  摘要：

  The Gcn5-related N-acetyltransferases (GNAT) comprise one of the largest enzyme superfamilies, with over 10 000 known members represented in all kingdoms of life. ChloroacetylCoenzymeA was prepared and demonstrated to be a substrate for several GNAT members. ChloroacetylCoA (ClAcCoA) is used by the Hat1 histone acetyltransferase to correctly acetylate histone H4 in a mixture of histone proteins. Chloroacetylation can be assessed by the subsequent reaction of the chloroacetylated product with thiol-containing compounds, including those with fluorescent or affinity (His8) tags. The bacterial RimL N-acetyltransferase also uses ClAcCoA to chloroacetyl the alpha-amino group of its cognate substrate, the ribosomal L12 protein, and this reaction can be observed in crude extracts. ChloroacetylCoA is a reagent that can be used to identify the unknown substrate(s) for this large family of functionally uncharacterized enzymes.

  DOI：

  10.1021/ja066298w

文献信息

• Chemical Reporters of Protein Acylation
  申请人：HANG HOWARD C.

  公开号：US20100203647A1

  公开（公告）日：2010-08-12

  Methods and kits for detecting acylated proteins produced by cells that have been cultured or by cells within an organism are provided. Also provided are methods and kits for detecting acylated proteins produced by cells where affinity purification tags are that facilitate detection are used. Compounds useful for the detection of acylated proteins are also provided.

  提供了用于检测已被培养的细胞产生的酰化蛋白或生物体内细胞产生的酰化蛋白的方法和试剂盒。还提供了用于检测已使用亲和纯化标签的细胞产生的酰化蛋白的方法和试剂盒，以便进行检测。还提供了用于检测酰化蛋白的化合物。
• Heterologous pathway to produce terpenes
  申请人：The Regents of the University of California

  公开号：US10167488B2

  公开（公告）日：2019-01-01

  Cells comprising a heterologous metabolic pathway are configured to produce a terpene product containing non-multiples of five carbon, particularly wherein the pathway comprises heterologous Lepidoptera insect juvenile hormone biosynthetic pathway enzymes of the insect's mevalonate pathway.

  包含异源代谢途径的细胞被配置为生产含有非五碳倍数的萜烯产品，特别是其中的途径包含昆虫甲羟戊酸途径的异源鳞翅目昆虫幼虫激素生物合成途径酶。
• KAS-III free FA synthesis
  申请人：WILLIAM MARSH RICE UNIVERSITY

  公开号：US10851393B2

  公开（公告）日：2020-12-01

  The present disclosure describes a genetically engineered a KASIII-independent fatty acid biosynthetic pathway that makes use of the promiscuous nature of the rest of the FAS enzymes (3-ketoacyl-ACP synthetase, 3-ketoacyl-ACP reductase, 3-hydroxyacyl ACP dehydrase, enoyl-ACP reductase) to bypass the KASIII step by providing a Co-A precursor of two or higher than two carbons (such as the four carbon butyryl-CoA) as the starting molecule. Since many CoA-based starter molecules can be supplied for the fatty acid synthesis, much more diversified products can be obtained with various carbon-chain lengths. As such, this disclosure will serve as a powerful and efficient platform to produce low to medium chain length products carrying many different functional groups.

  本公开描述了一种基因工程设计的不依赖 KASIII 的脂肪酸生物合成途径，该途径利用 FAS 其余酶（3-酮酰-ACP 合成酶、3-酮酰-ACP 还原酶、3-羟基乙酰 ACP 脱水酶、烯酰-ACP 还原酶）的杂合性，通过提供一个或多个 Co-A 前体，绕过 KASIII 步骤、3-Ketoacyl-ACP 还原酶、3-hydroxyacyl ACP 脱水酶、enoyl-ACP 还原酶），通过提供两个或两个以上碳原子的 Co-A 前体（如四碳丁酰-CoA）作为起始分子，绕过 KASIII 步骤。由于可以为脂肪酸合成提供多种以 CoA 为基础的起始分子，因此可以获得具有不同碳链长度的更多样化的产品。因此，本发明将成为生产携带多种不同官能团的中低链长产品的强大而高效的平台。
• Malonyl-coenzyme A mimics as fatty acid synthase inhibitors and methods of use
  申请人：Purdue Research Foundation

  公开号：US11008362B2

  公开（公告）日：2021-05-18

  The present disclosure generally relates to novel compounds as a fatty acid synthase inhibitor useful for the treatment of infection diseases, cancers, or metabolic diseases that malfunction of fatty acid synthase is involved. In particular this present invention directs to malonyl-coenzyme A (CoA) mimetics and methods of use thereof. The invention described herein also pertains to pharmaceutical compositions and methods for treating diseases in mammals using compounds disclosed herein.

  本发明一般涉及作为脂肪酸合成酶抑制剂的新型化合物，可用于治疗涉及脂肪酸合成酶功能失常的感染性疾病、癌症或代谢性疾病。本发明尤其涉及丙二酰辅酶 A（CoA）模拟物及其使用方法。本发明还涉及使用本发明公开的化合物治疗哺乳动物疾病的药物组合物和方法。
• METHODS AND COMPOSITIONS FOR THE TREATMENT OF CELL PROLIFERATION
  申请人：Interstitial Therapeutics

  公开号：EP1789029A2

  公开（公告）日：2007-05-30