malonyl CoA | 524-14-1

• 物质功能分类: 生物 - ELISA 试剂盒
• 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: malonyl CoA
• 英文别名: malonyl-CoA；molonyl-CoA；S-carboxyacetyl-coenzyme-A；Unii-lnb9ycj9F9；3-[2-[3-[[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]ethylsulfanyl]-3-oxopropanoic acid
• CAS: 524-14-1
• 化学式: C₂₄H₃₈N₇O₁₉P₃S
• 分子量: 853.589
• InChiKey: LTYOQGRJFJAKNA-VFLPNFFSSA-N

物化性质

• 密度：
  1.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -5.9
• 重原子数：
  54
• 可旋转键数：
  22
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  426
• 氢给体数：
  10
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  malonyl CoA 在 乙二胺四乙酸 、 recombinant pentaketide synthase 作用下， 以 phosphate buffer 为溶剂， 反应 18.0h， 生成 去甲丁香色原酮
  参考文献：
  名称：

  A Plant Type III Polyketide Synthase that Produces Pentaketide Chromone

  摘要：

  A novel plant-specific type III polyketide synthase (PKS) that catalyzes formation of a pentaketide chromone, 5,7-dihydroxy-2-methylchromone, from five molecules of malonyl-CoA, was cloned and sequenced from aloe (Aloe arborescens). Site-directed mutagenesis revealed that Met207 (corresponding to Thr197 in CHS) determines the polyketide chain length and the product specificity of the enzyme; remarkably, replacement of a single amino acid residue, Met207, with Gly yielded a mutant enzyme that efficiently produces aromatic octaketides, SEK4 and SEK4b, the products of the minimal PKS for actinorhodin (act from Streptomyces coelicolor), from eight molecules of malonyl-CoA. This provided new insights into the catalytic functions and specificities of the CHS-superfamily type III PKS enzymes.

  DOI：

  10.1021/ja0431206
• 作为产物：
  描述：

  丙二酸 、 coenzyme A 在 malonyl-CoA synthetase from Rhizobium trifolii 、 5’-三磷酸腺苷 、 magnesium chloride 作用下， 以 aq. phosphate buffer 为溶剂， 反应 3.0h， 生成 malonyl CoA
  参考文献：
  名称：

  通过工程酰基辅酶A合成酶揭示了多特异性反式酰基转移酶机制

  摘要：

  聚酮化合物合酶通过增量剂单元和酰基硫酯的缩合来构建具有多种结构和生物活性的聚酮化合物。尽管越来越多的证据表明，聚酮化合物合酶可能在体外和体内都可以耐受非天然扩展剂由于缺乏合成多种酰基辅酶A增量剂单元的途径，旨在探索和利用聚酮化合物合酶特异性的研究被严格限制在仅少量的增量剂单元中。在这里，我们报告了混杂的丙二酰-CoA合成酶变体的构建，该变体可用于合成在C2位置取代的大范围的丙二酰-CoA扩展剂单元，其中一些包含用于化学选择性连接的手柄，在天然生物合成中未发现系统。我们通过探究几种反式的酰基辅酶A特异性突出了这些酶的效用。-酰基转移酶，导致对非天然延伸单元的多特异性的空前发现，其中几种在天然生物合成途径中未发现。这些结果表明，聚酮化合物的生物合成机制对非天然底物的耐受性可能比以前建立的更高，并且突变体合成酶是探测生物合成机制特异性的有价值的工具。我们的数据提出了利用这种滥交和实现聚酮化合物的区域选择性修饰的新的合成生物学策略。

  DOI：

  10.1021/cb3003489

文献信息

• Enzymatic formation of long-chain polyketide pyrones by plant type III polyketide synthases
  作者：Ikuro Abe、Tatsuya Watanabe、Hiroshi Noguchi

  DOI：10.1016/j.phytochem.2004.08.005

  日期：2004.9

  synthase (CHS) from Scutellaria baicalensis and stilbene synthase (STS) from Arachis hypogaea accepted CoA esters of long-chain fatty acid (CHS up to the C12 ester, while STS up to the C14 ester) as a starter substrate, and carried out sequential condensations with malonyl-CoA, leading to formation of triketide and tetraketide alpha-pyrones. Interestingly, the C6, C8, and C10 esters were kinetically

  黄芩的重组查耳酮合酶 (CHS) 和花生的二苯乙烯合酶 (STS) 接受长链脂肪酸的 CoA 酯（CHS 到 C12 酯，而 STS 到 C14 酯）作为起始底物，并携带与丙二酰辅酶A连续缩合，导致三酮和四酮α-吡喃酮的形成。有趣的是，与生理起始底物相比，C6、C8 和 C10 酯在动力学上更受酶的青睐。kcat/KM 值比对香豆酰辅酶 A 高 1.2 至 1.9 倍。这些酶的催化多样性为 III 型 PKS 反应提供了进一步的机理见解，并表明 CHS 超家族酶参与了植物中长链烷基多酚（如漆酚和银杏酸）的生物合成。
• Production of malonyl-CoA derived products via anaerobic pathways
  申请人：LALLEMAND HUNGARY LIQUIDITY MANAGEMENT LLC

  公开号：US11162125B2

  公开（公告）日：2021-11-02

  The present invention provides for novel metabolic pathways to convert biomass and other carbohydrate sources to malonyl-CoA derived products, such as hydrocarbons and other bioproducts, under anaerobic conditions and with the net production of ATP. More specifically, the invention provides for a recombinant microorganism comprising one or more native and/or heterologous enzymes that function in one or more engineered metabolic pathways to achieve conversion of a carbohydrate source to, e.g., long-chain hydrocarbons and hydrocarbon derivatives, wherein the one or more native and/or heterologous enzymes is activated, upregulated, downregulated, or deleted. The invention also provides for processes to convert biomass to malonyl-CoA derived products which comprise contacting a carbohydrate source with a recombinant microorganism of the invention.

  本发明提供了新的代谢途径，可在厌氧条件下将生物质和其他碳水化合物源转化为丙二酰-CoA 衍生产品，如碳氢化合物和其他生物产品，并净产生 ATP。更具体地说，本发明提供了一种重组微生物，该微生物包含一种或多种本源和/或异源酶，这些酶在一种或多种工程代谢途径中发挥作用，以实现碳水化合物源到例如长链碳氢化合物和碳氢化合物衍生物的转化，其中一种或多种本源和/或异源酶被激活、上调、下调或删除。本发明还提供了将生物质转化为丙二酰-CoA 衍生产品的工艺，该工艺包括将碳水化合物源与本发明的重组微生物接触。
• Cylindrocyclophane Biosynthesis Involves Functionalization of an Unactivated Carbon Center
  作者：Hitomi Nakamura、Hilary A. Hamer、Gopal Sirasani、Emily P. Balskus

  DOI：10.1021/ja308318p

  日期：2012.11.14

  The cylindrocyclophanes are a family of natural products that share a remarkable paracyclophane carbon scaffold. Using genome sequencing and bioinformatic analyses; we have discovered a biosynthetic gene cluster involved in the assembly of cylindrocyclophane F. Through a combination of in vitro enzyme characterization and feeding Studies, We Confirm the connection between this gene cluster and cylindrocyclophane production, elucidate the chemical events involved in initiating and terminating an unusual type I polyketide synthase assembly line, and discover that macrocycle assembly involves functionalization of an unactivated carbon center.
• Substrate Specificity of Chalcone Synthase:  Enzymatic Formation of Unnatural Polyketides from Synthetic Cinnamoyl-CoA Analogues
  作者：Ikuro Abe、Hiroyuki Morita、Ayumi Nomura、Hiroshi Noguchi

  DOI：10.1021/ja0027113

  日期：2000.11.1
• Enzymatic formation of an unnatural methylated triketide by plant type III polyketide synthases
  作者：Tsuyoshi Abe、Hisashi Noma、Hiroshi Noguchi、Ikuro Abe

  DOI：10.1016/j.tetlet.2006.10.012

  日期：2006.12

  Octaketide synthase, a novel plant-specific type III polyketide synthase from Aloe arborescens, efficiently accepted (2RS)-methylmalonyl-CoA as a sole substrate to produce 6-ethyl-4-hydroxy-3,5-dimethyl-2-pyrone. On the other hand, a tetraketide-producing chalcone synthase from Scutellaria baicalensis and a diketide-producing benzalacetone synthase from Rheum palmatum also yielded the unnatural methylated C-9 triketide pyrone as a single product by sequential decarboxylative condensations of three molecules of (2RS)-methylmalonyl-CoA. (c) 2006 Elsevier Ltd. All rights reserved.