4-methylpentanoyl-CoA

• 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: 4-methylpentanoyl-CoA
• 英文别名: 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] 4-methylpentanethioate
• 化学式: C₂₇H₄₆N₇O₁₇P₃S
• 分子量: 865.686
• InChiKey: GESPQCUXDWNNGU-HDRQGHTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4
• 重原子数：
  55
• 可旋转键数：
  23
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  4-methylpentenoyl-CoA 在 Caulobacter crescentus crotonyl-CoA carboxylase/reductase 、 碳酸氢钠 、 还原型辅酶II(NADPH)四钠盐 作用下， 反应 3.0h， 生成 4-methylpentanoyl-CoA
  参考文献：
  名称：

  从中心代谢和聚酮化合物的生物合成中筛选和工程化羧化还原酶的合成潜力

  摘要：

  羧化烯酰硫酯还原酶（ECR）是最近发现的一类酶。它们催化高效添加CO 2与α，β-不饱和CoA-硫酯的双键结合，具有两个生物学功能。在许多细菌的初级代谢中，它们在吸收中央代谢物乙酰辅酶A的过程中会产生乙基丙二酰辅酶A。在次级代谢中，它们提供独特的α-羧基-酰基-硫代酯，以改变许多聚酮化合物天然产物的主链。使用各种可能的底物库系统评估了不同的ECR。我们鉴定了三个活性位点残基，以区分仅限于C4和C5-烯酰基-CoA的ECR和高度混杂的ECR，并成功地设计了一种选定的ECR作为原理证明。这项研究定义了ECR反应性的分子基础，从而可以预测和操纵天然产物多样化中的关键反应。

  DOI：

  10.1002/anie.201505282

文献信息

• Repurposing the 3‐Isocyanobutanoic Acid Adenylation Enzyme SfaB for Versatile Amidation and Thioesterification
  作者：Mengyi Zhu、Lijuan Wang、Jing He

  DOI：10.1002/anie.202010042

  日期：2021.1.25

  molecules with novel skeletons, but also to identify the enzymes that catalyze diverse chemical reactions. Exploring the substrate promiscuity and catalytic mechanism of those biosynthetic enzymes facilitates the development of potential biocatalysts. SfaB is an acyl adenylate‐forming enzyme that adenylates a unique building block, 3‐isocyanobutanoic acid, in the biosynthetic pathway of the diisonitrile

  微生物天然产物的基因组挖掘使化学家不仅能够发现具有新颖骨架的生物活性分子，而且能够识别催化多种化学反应的酶。探索这些生物合成酶的底物混杂性和催化机理有助于开发潜在的生物催化剂。SfaB是一种形成酰基腺苷酸的酶，可在由硫链霉菌产生的二异腈自然产物SF2768的生物合成途径中，对独特的结构单元3-异氰基丁酸进行腺苷酸化。，并且该AMP连接酶被证明可以接受各种短链脂肪酸（SCFA）。在本文中，我们将SfaB重新用于催化那些SCFA与各种胺或硫醇亲核试剂之间的酰胺化或硫酯化反应，从而提供了另一种酶促方法来体外制备相应的酰胺和硫酯。
• Biosynthesis of Branched-chain Fatty Acid in<i>Bacilli</i>: FabD (malonyl-CoA:ACP transacylase) Is Not Essential for<i>In Vitro</i>Biosynthesis of Branched-chain Fatty Acids
  作者：Hirosuke OKU、Naoya FUTAMORI、Kenichi MASUDA、Yumiko SHIMABUKURO、Tomoyo OMINE、Hironori IWASAKI

  DOI：10.1271/bbb.67.2106

  日期：2003.1

  It was found that the partially purified β-ketoacyl-ACP synthase of Bacillus insolitus did not require the addition of FabD (malonyl-CoA:ACP transacylase, MAT) for the activity assay. This study therefore examined the necessity of FabD protein for in vitro branched-chain fatty acid (BCFA) biosynthesis by crude fatty acid synthetases (FAS) of Bacilli. To discover the involvement of FabD in the BCFA biosynthesis, the protein was removed from the crude FAS by immunoprecipitation. The His-tag fusion protein FabD of Bacillus subtilis was expressed in Escherichia coli and used for the preparation of antibody. The rabbit antibody raised against the expressed fusion protein specifically recognized the FabD in the crude FAS of B. subtilis. Evaluation of the efficacy of the immunoprecipitation showed that a trace of FabD protein was present in the antibody-treated crude FAS. However, this complete removal of FabD from the crude FAS did not abolish its BCFA biosynthesis, but only reduced the level to 50-60% of the control level for acyl-CoA primer and to 80% for α-keto-β-methylvalerate primer. Furthermore, the FabD concentration did not necessarily correlate with the MAT specific activity in the enzyme fractions, suggesting the presence of another enzyme source of MAT activity. This study, therefore, suggests that FabD is not the sole enzyme source of MAT for in vitro BCFA biosynthesis, and implies the existence of a functional connection between fatty acid biosynthesis and another metabolic pathway.

  研究发现，不完全纯化的无枝菌酸菌β-酮脂酰ACP合酶（Bacillus insolitus）在活性测定时不需要添加FabD（丙二酸单酰-CoA:ACP转酰酶，MAT）。因此，本研究探讨了杆状菌粗脂肪酸合成酶（FAS）体外支链脂肪酸（BCFA）生物合成中FabD蛋白的必要性。为了探索FabD在BCFA生物合成中的作用，通过免疫沉淀法从粗FAS中去除该蛋白。将枯草芽孢杆菌的His标签融合蛋白FabD在大肠杆菌中表达，并用其制备抗体。针对表达的融合蛋白免疫兔子得到的抗体能特异性地识别枯草芽孢杆菌粗FAS中的FabD。免疫沉淀法效力评估显示，经抗体处理的粗FAS中仅残留极少量的FabD蛋白。然而，从粗FAS中完全去除FabD并未使其BCFA生物合成失活，仅使其活性降低，对于酰基-CoA引物降至对照组的50-60%，对于α-酮基-β-甲基戊酸引物降至80%。此外，FabD浓度与酶组分中MAT的特异性活性并不一定相关，表明存在另一种MAT活性的酶源。因此，本研究认为，FabD不是体外BCFA生物合成中MAT唯一的酶源，并暗示脂肪酸生物合成与其他代谢途径之间存在功能联系。
• Microbial production of branched medium chain alcohols, such as 4-methylpentanol
  申请人：Massachusetts Institute of Technology

  公开号：US10100335B2

  公开（公告）日：2018-10-16

  The invention relates to recombinant cells and their use in in the production of branched medium-chain alcohols such as 4-methyl-1-pentanol.

  本发明涉及重组细胞及其在生产支链中链醇，如 4-甲基-1-戊醇中的应用。
• METHODS FOR BIOSYNTHESIZING 1,3BUTADIENE
  申请人：INVISTA Technologies S.à.r.l.

  公开号：EP2785848A2

  公开（公告）日：2014-10-08
• MICROBIAL PRODUCTION OF BRANCHED MEDIUM CHAIN ALCOHOLS, SUCH AS 4-METHYLPENTANOL
  申请人：Massachusetts Institute of Technology

  公开号：US20150132816A1

  公开（公告）日：2015-05-14

  The invention relates to recombinant cells and their use in the production of branched medium-chain alcohols such as 4-methyl-1-pentanol.