丙二酰辅酶A-钠盐 | 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
• 中文名称: 丙二酰辅酶A-钠盐
• 英文名称: S-(hydrogen malonyl)coenzyme A
• 英文别名: malonyl-CoA；Malonyl coenzyme A；3-[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]ethylsulfanyl]-3-oxopropanoic acid
• CAS: 524-14-1
• 化学式: C₂₄H₃₈N₇O₁₉P₃S
• 分子量: 853.589
• InChiKey: LTYOQGRJFJAKNA-DVVLENMVSA-N

物化性质

• 密度：
  1.95±0.1 g/cm3(Predicted)
• 物理描述：
  Solid
• 碰撞截面：
  253.05 Ų [M-H]- [CCS Type: DT, Method: stepped-field]

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

制备方法与用途

丙二酰辅酶A不仅是脂肪酸生物合成的底物，还是脂肪酸氧化的抑制剂。此外，它也是线粒体肉碱棕榈酰转移酶（CPT）的一种可逆抑制剂。[1][2]

反应信息

• 作为反应物：
  描述：

  丙二酰辅酶A-钠盐 在 potassium phosphate buffer 、 乙二胺四乙酸 、 G₂₀₇W mutated octaketide synthase 作用下， 反应 18.0h， 生成 4-hydroxy-6-(2-oxopropyl)pyran-2-one
  参考文献：
  名称：

  植物聚酮化合物的工程生物合成：生产八肽的植物 III 型聚酮化合物合成酶中的链长控制

  摘要：

  III 型聚酮化合物合酶 (PKS) 的查尔酮合酶 (CHS) 超家族产生多种具有显着结构多样性和生物活性的植物次级代谢产物（例如查耳酮、芪、二苯甲酮、丙烯、间苯三酚、间苯二酚、吡喃酮和色酮）。在这里，我们描述了一种来自芦荟（Aloe arborescens）的产生八酮化合物的新型植物特异性 III 型 PKS，与其他植物 CHS 超家族酶具有 50-60% 的氨基酸序列同一性。在大肠杆菌中表达的重组酶催化丙二酰辅酶 A 的七次连续脱羧缩合反应，产生芳香族八酮化合物 SEK4 和 SEK4b，这是已知由结构简单的 III 型 PKS 合成的最长的聚酮化合物。令人惊讶的是，定点诱变显示单个残基 Gly207（对应于 CHS' s 活性位点 Thr197) 决定了聚酮链长度和产品特异性。从小到大的取代（G207A、G207T、G207M、G207L、G207F 和 G207W）导致八酮化合物形

  DOI：

  10.1021/ja053945v
• 作为产物：
  描述：

  乙酰辅酶A 在 Acetobacter aceti succinyl-CoA:acetate CoA transferase C-terminal hexahistidine-tagged 作用下， 以 aq. buffer 为溶剂， 生成 丙二酰辅酶A-钠盐
  参考文献：
  名称：

  Crystal Structures of Acetobacter aceti Succinyl-Coenzyme A (CoA):Acetate CoA-Transferase Reveal Specificity Determinants and Illustrate the Mechanism Used by Class I CoA-Transferases

  摘要：

  Coenzyme A (CoA)-transferases catalyze transthioesterification reactions involving acyl-CoA substrates, using an active-site carboxylate to form covalent acyl anhydride and CoA thioester adducts. Mechanistic studies of class I CoA-transferases suggested that acyl-CoA binding energy is used to accelerate rate-limiting acyl transfers by compressing the substrate thioester tightly against the catalytic glutamate [White, H., and Jencks, W. P. (1976) J. Biol. Chem. 251, 1688-1699]. The class I CoA-transferase succinyl-CoA:acetate CoA-transferase is an acetic acid resistance factor (AarC) with a role in a variant citric acid cycle in Acetobacter aceti. In an effort to identify residues involved in substrate recognition, X-ray crystal structures of a C-terminally His(6)-tagged form (AarCH6) were determined for several wild-type and mutant complexes, including freeze trapped acetylglutamyl anhydride and glutamyl-CoA thioester adducts. The latter shows the acetate product bound to an auxiliary site that is required for efficient carboxylate substrate recognition. A mutant in which the catalytic glutamate was changed to an alanine crystallized in a closed complex containing dethiaacetyl-CoA, which adopts an unusual curled conformation. A model of the acetyl-CoA Michaelis complex demonstrates the compression anticipated four decades ago by Jencks and reveals that the nucleophilic glutamate is held at a near-ideal angle for attack as the thioester oxygen is forced into an oxyanion hole composed of Gly388 NH and CoA N2 ''. CoA is nearly immobile along its entire length during all stages of the enzyme reaction. Spatial and sequence conservation of key residues indicates that this mechanism is general among class I CoA-transferases.

  DOI：

  10.1021/bi300957f
• 作为试剂：
  描述：

  4-香豆酸 、 辅酶 A 在 Arabidopsis thaliana 4-coumaroyl-CoA ligase-(Gly–Ser–Gly)-Vitis vinifera stilbene synthase fusion protein 、 5’-三磷酸腺苷 、 丙二酰辅酶A-钠盐 作用下， 以 aq. phosphate buffer 为溶剂， 反应 0.5h， 生成 [(2R,3S,4R,5R)-5-(6-氨基嘌呤-9-基)-4-羟基-2-[[羟基-[羟基-[3-羟基-3-[2-[2-[(E)-3-(4-羟基苯基)丙-2-烯酰基]硫基乙基氨基甲酰]乙基氨基甲酰]-2,2-二甲基-丙氧基]磷酰]氧基-磷酰]氧基甲基]四氢呋喃-3-基]氧基膦酸
  参考文献：
  名称：

  Effect of flexible linker length on the activity of fusion protein 4-coumaroyl-CoA ligase::stilbene synthase

  摘要：

  "灵活的连接器长度直接影响融合蛋白4CL::STS的催化效率。"

  DOI：

  10.1039/c6mb00563b

文献信息

• [EN] ACC INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE L'ACC ET UTILISATIONS ASSOCIÉES
  申请人：GILEAD APOLLO LLC

  公开号：WO2017075056A1

  公开（公告）日：2017-05-04

  The present invention provides compounds I and II useful as inhibitors of Acetyl CoA Carboxylase (ACC), compositions thereof, and methods of using the same.

  本发明提供了化合物I和II，这些化合物可用作乙酰辅酶A羧化酶（ACC）的抑制剂，以及它们的组合物和使用方法。
• [EN] NOVEL COMPUNDS, PHARMACEUTICAL COMPOSITIONS CONTAINING SAME, AND METHODS OF USE FOR SAME<br/>[FR] NOUVEAUX COMPOSÉS, COMPOSITIONS PHARMACEUTIQUES LES CONTENANT ET MÉTHODES D'UTILISATION DESDITS COMPOSÉS
  申请人：FASGEN INC

  公开号：WO2004005277A1

  公开（公告）日：2004-01-15

  A pharmaceutical composition comprising a phamaceurtical diluent and a compound of formula IV wherein R21= H, C1-C20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, or alkylaryl, -CH2OR25, -C(O)R25, -CO(O)R25, -C(O)NR25R26, -CH2C(O)R25, or -CH2C(O)NHR25, where R25 and R26 are each independently H, C1-C10 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, or alkylaryl, optionally containing one or more halogen atoms. R22 = -OH, -OR27, -OCH2C(O)R27, -OCH2C(O)NHR27, -OC(O)R27, -OC(O)OR27, -OC(O)NHNH-R5, or -OC(O)NR27R28, where R27 and R28 are each independentlyH, C1 -C20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, or alkylaryl, and where R27 and R28 can each optionally contain halogen atoms; R23 and R24, the same or different from each other, are C1-C20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, or alkylaryl. Methods of using such formulations for the treatment of cancer, to effect weight loss, to treat microbially-based infections, to inhibit neuropeptide-Y and/or fatty acid synthase, and to stimulate CPT-1.

  一种包括药用稀释剂和化合物IV的药物组合物，其中R21= H，C1-C20烷基，环烷基，烯基，芳基，芳基烷基或烷基芳基，-CH2OR25，-C(O)R25，-CO(O)R25，-C(O)NR25R26，-CH2C(O)R25或-CH2C(O)NHR25，其中R25和R26各自独立地为H，C1-C10烷基，环烷基，烯基，芳基，芳基烷基或烷基芳基，可选地含有一个或多个卤素原子。R22 = -OH，-OR27，-OCH2C(O)R27，-OCH2C(O)NHR27，-OC(O)R27，-OC(O)OR27，-OC(O)NHNH-R5或-OC(O)NR27R28，其中R27和R28各自独立地为H，C1-C20烷基，环烷基，烯基，芳基，芳基烷基或烷基芳基，且R27和R28各自可选地含有卤素原子；R23和R24，相同或不同，为C1-C20烷基，环烷基，烯基，芳基，芳基烷基或烷基芳基。使用这种配方治疗癌症，减轻体重，治疗微生物感染，抑制神经肽Y和/或脂肪酸合酶，以及刺激CPT-1的方法。
• Compounds and uses thereof for decreasing activity of hormone-sensitive lipase
  申请人：——

  公开号：US20030166644A1

  公开（公告）日：2003-09-04

  Use of compounds to inhibit hormone-sensitive lipase, pharmaceutical compositions comprising the compounds, methods of treatment employing these compounds and compositions, and novel compounds. The present compounds are inhibitors of hormone-sensitive lipase and may be useful in the treatment and/or prevention of medical disorders where a decreased activity of hormone-sensitive lipase is desirable.

  使用化合物抑制激素敏感性脂肪酶，包括这些化合物的药物组合物，使用这些化合物和组合物的治疗方法，以及新化合物。目前的化合物是激素敏感性脂肪酶的抑制剂，可能在治疗和/或预防需要降低激素敏感性脂肪酶活性的医学疾病中有用。
• New pyrrolidine derivatives, pharmaceutical compositions and uses thereof
  申请人：FLECK Martin

  公开号：US20140100211A1

  公开（公告）日：2014-04-10

  Pyrrolidine derivatives of the formula and their use as medicaments for the treatment of obesity and type 2 diabetes.

  吡咯烷衍生物的化学式及其作为治疗肥胖和2型糖尿病药物的用途。
• TRIAZOLE ACC INHIBITORS AND USES THEREOF
  申请人：Gilead Apollo, LLC

  公开号：US20170166584A1

  公开（公告）日：2017-06-15

  The present invention provides triazole compounds useful as inhibitors of Acetyl CoA Carboxylase (ACC), compositions thereof, and methods of using the same.

  本发明提供了三唑化合物，可用作乙酰辅酶A羧化酶（ACC）的抑制剂，以及其组合物和使用方法。