4-hydroxy-6-(2-oxoheptyl)pyran-2-one | 327175-05-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 4-hydroxy-6-(2-oxoheptyl)pyran-2-one
• 英文别名: 4-hydroxy-6-(2-oxoheptyl)-2-pyrone；hexanoyl triacetic acid lactone；4-hydroxy-6-(2-oxoheptyl)-2H-pyran-2-one
• CAS: 327175-05-3
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: GHURLXDGHMZIGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  S-2-acetamidoethyl hexanethioate 在 1,4-dithio-D,L-threitol 、 chalcone synthase, immobilized onto Ni-nitrilotriacetic acid agarose 、 malonyl-CoA synthetase, immobilized onto glutathione-sepharose 、 sodium malonate 、 adenosine 5'-triphosphate disodium salt 、 辅酶 A 、 magnesium chloride 作用下， 反应 72.0h， 以54%的产率得到4-羟基-6-戊基吡喃-2-酮
  参考文献：
  名称：

  In Vitro Precursor-Directed Synthesis of Polyketide Analogues with Coenzyme A Regeneration for the Development of Antiangiogenic Agents

  摘要：

  Polyketide analogues are produced via in vitro reconstruction of a precursor-directed polyketide biosynthetic pathway. Malonyl-CoA synthetase (MCS) was used in conjunction with chalcone synthase (CHS), thereby allowing efficient use of synthetic starter molecules and malonate as extender. Coenzyme-A was recycled up to 50 times. The use of a simple immobilization procedure resulted in up to a 30-fold higher yield of pyrone CHS products than that obtained with the free enzyme solutions.

  DOI：

  10.1021/ol901243e

文献信息

• Exploiting the Reaction Flexibility of a Type III Polyketide Synthase through in Vitro Pathway Manipulation
  作者：Jae-Cheol Jeong、Aravind Srinivasan、Sabine Grüschow、Horacio Bach、David H. Sherman、Jonathan S. Dordick

  DOI：10.1021/ja0441559

  日期：2005.1.1

  synthesis of the pentaketide flaviolin and its dimeric derivative, and a wide range of pyrones and their coupled derivatives with flaviolin, as well as their halogenated derivatives. The addition of acyl-CoA oxidase to the pathway prior to the polyketide synthase resulted in unsaturated pyrone side chains, further broadening the product spectrum that can be achieved. The approach developed in this work

  在体外构建了一个合成代谢途径，包括来自天蓝色链霉菌的 III 型聚酮化合物合酶和来自大豆和烟熏蓝藻（氯过氧化物酶）的过氧化物酶。这导致合成了五肽黄素及其二聚衍生物，以及广泛的吡喃酮及其与黄素的偶联衍生物，以及它们的卤化衍生物。在聚酮合酶之前将酰基辅酶A氧化酶添加到途径中导致不饱和的吡喃酮侧链，进一步拓宽了可以实现的产物谱。因此，这项工作中开发的方法为在复杂天然产物衍生物的合成中利用生物催化提供了一种新模型。
• [EN] PREPARING AND MODIFYING MEROTERPENE POLYKETIDES, KETONES, AND LACTONES FOR CANNABINOID SEMISYNTHESIS<br/>[FR] PRÉPARATION ET MODIFICATION DE POLYCÉTIDES DE MÉROTERPÈNES, DE CÉTONES ET DE LACTONES POUR LA SEMI-SYNTHÈSE DE CANNABINOÏDES
  申请人：LYGOS INC

  公开号：WO2021163042A1

  公开（公告）日：2021-08-19

  Provided herein are processes, including semi-synthetic, and synthetic processes for preparing cannabinoids, and cannabinoid compositions provided thereby.

  本文提供了制备大麻素的过程，包括半合成和全合成过程，以及由此提供的大麻素组合物。
• 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。
• Genes and proteins for aromatic polyketide synthesis
  申请人：National Research Council of Canada

  公开号：US10718000B2

  公开（公告）日：2020-07-21

  Nucleic acid molecules encoding polypeptides having polyketide synthase activity have been identified and characterized. Expression or over-expression of the nucleic acids alters levels of cannabinoid compounds in organisms. The polypeptides may be used in vivo or in vitro to produce cannabinoid compounds.

  已鉴定出编码具有多酮合成酶活性的多肽的核酸分子，并对其进行了表征。核酸的表达或过度表达可改变生物体内大麻素化合物的水平。多肽可用于体内或体外生产大麻素化合物。
• Alkylresorcylic acid synthesis by type III polyketide synthases from rice Oryza sativa
  作者：Miku Matsuzawa、Yohei Katsuyama、Nobutaka Funa、Sueharu Horinouchi

  DOI：10.1016/j.phytochem.2010.02.012

  日期：2010.7

  Alkylresorcinols, produced by various plants, bacteria, and fungi, are bioactive compounds possessing beneficial activities for human health, such as anti-cancer activity. In rice, they accumulate in seedlings, contributing to protection against fungi. Alkylresorcylic acids, which are carboxylated forms of alkylresorcinols, are unstable compounds and decarboxylate readily to yield alkylresorcinols. Genome mining of the rice Oryza sativa identified two type III polyketide synthases, named ARAS1 (alkylresorcylic acid synthase) and ARAS2, that catalyze the formation of alkylresorcylic acids. Both enzymes condensed fatty acyl-CoAs with three C-2 units from malonyl-CoA and cyclized the resulting tetraketide intermediates via intramolecular C-2 to C-7 aldol condensation. The alkylresorcylic acids thus produced were released from the enzyme and decarboxylated non-enzymatically to yield alkylresorcinols. This is the first report on a plant type III polyketide synthase that produces tetraketide alkylresorcylic acids as major products. (C)2010 Published by Elsevier Ltd.