2-(二羟基甲基)-2-羟基-2H-吡喃-3(6H)-酮 | 59896-20-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 中文名称: 2-(二羟基甲基)-2-羟基-2H-吡喃-3(6H)-酮
• 英文名称: cortalcerone
• 英文别名: 2-hydroxy-3-oxo-3,6-dihydro-2H-pyran-2-carbaldehyde hydrate；2-dihydroxymethyl-2-hydroxy-6H-pyran-3-one；6-hydroxy-2,3-dioxo-hex-4c-enal 2->6-cyclohemiacetal 1-hydrate；2-(Dihydroxymethyl)-2-hydroxy-2H-pyran-3(6H)-one；6-(dihydroxymethyl)-6-hydroxy-2H-pyran-5-one
• CAS: 59896-20-7
• 化学式: C₆H₈O₅
• 分子量: 160.127
• InChiKey: CCBGJZIXYONESN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(二羟基甲基)-2-羟基-2H-吡喃-3(6H)-酮 在 Al-Sn-beta 作用下， 以 甲醇 、 水 为溶剂， 反应 0.5h， 生成 alpha-羟基呋喃-2-乙酸
  参考文献：
  名称：

  化学和生物催化的整合：通过葡萄糖通过葡萄糖从糠醛生产呋喃基乙醇酸

  摘要：

  呋喃基乙醇酸（FA）是一种适合与乳酸共聚的假芳族羟基酸，可以使用Brønsted和Lewis酸催化剂的组合，通过酶促衍生的丙酮酸从葡萄糖中制得。首先将Corcercerone在布朗斯台德酸位点（HCl或含Al的β沸石）上转化为呋喃乙二醛水合物（FH），然后在路易斯酸位点（Sn-β沸石）上将FH转化为FA。使用四氢呋喃（THF）作为溶剂在358 K时，将FH转化为FA的选择性高达12％时高达80％。FH的较高转化率导致FA催化FH降解并随后通过沉积使催化剂失活碳质残留物。失活的催化剂可以通过煅烧再生。可以从10％葡萄糖溶液中使用重组蛋白生产Corcercerone从木腐真菌Phanerochaete chrysosporium BKM-F-1767表达吡喃糖2-氧化酶和醛糖-2-纤维素脱水酶的大肠杆菌菌株。在甲醇/水溶剂中，在具有布朗斯台德和路易斯酸位点的含铝Sn-β沸石上，在甲醇/水溶剂中

  DOI：

  10.1021/cs400593p
• 作为产物：
  描述：

  D-arabino-hexose-2-ulose 在 sodium hydroxide 、 sodium phosphate 作用下， 生成 2-(二羟基甲基)-2-羟基-2H-吡喃-3(6H)-酮
  参考文献：
  名称：

  Synthesis of the antibiotic cortalcerone from d-glucose using pyranose 2-oxidase and a novel fungal enzyme, aldos-2-ulose dehydratase

  摘要：

  Using two enzymes purified from the white-Tot fungus, PoLyporus obtusus, 5% solutions Of D-glucose have been quantitatively converted in vitro into D-arabino-hexos-2-ulose (D-glucosone) and subsequently into a compound having antimicrobial activity. The antibiotic has been shown by nuclear magnetic resonance and mass spectroscopy to be chemically identical to a previously described fungal metabolite known as cortalcerone. Based on kinetic analysis of the synthetic process, a pathway for the biosynthesis of cortalcerone is proposed, involving both chemical rearrangement and enzymically catalyzed steps. Two enzymes, pyranose 2-oxidase and a previously uncharacterized D-arabino-hexos-2-ulose-utilizing enzyme, may be sufficient for the biosynthesis of cortalcerone from glucose in vivo. The D-arabino-hexos-2-ulose-utilizing enzyme dehydrates certain aldosuloses and has been named aldos-2-ulose dehydratase. The enzyme, which appears to be a dimer of 95-kDa subunits, has been purified 450-fold. Additional properties of aldos-2-ulose dehydratase are described, including its apparent ability to catalyze two different steps in the proposed biosynthetic pathway for cortalcerone.

  DOI：

  10.1016/s0008-6215(00)90994-7

文献信息

• A convenient laboratory procedure for the preparation of cortalcerone, a fungal antibiotic β-pyrone
  作者：Jiři Gabriel、Jindřich Volc、Elena Kubátová、Zdena Palková、Martin Pospíšek

  DOI：10.1016/0008-6215(94)90025-6

  日期：1994.1
• Synthesis of the antibiotic cortalcerone from d-glucose using pyranose 2-oxidase and a novel fungal enzyme, aldos-2-ulose dehydratase
  作者：Kirston Koths、Robert Halenbeck、Margaret Moreland

  DOI：10.1016/s0008-6215(00)90994-7

  日期：1992.7

  Using two enzymes purified from the white-Tot fungus, PoLyporus obtusus, 5% solutions Of D-glucose have been quantitatively converted in vitro into D-arabino-hexos-2-ulose (D-glucosone) and subsequently into a compound having antimicrobial activity. The antibiotic has been shown by nuclear magnetic resonance and mass spectroscopy to be chemically identical to a previously described fungal metabolite known as cortalcerone. Based on kinetic analysis of the synthetic process, a pathway for the biosynthesis of cortalcerone is proposed, involving both chemical rearrangement and enzymically catalyzed steps. Two enzymes, pyranose 2-oxidase and a previously uncharacterized D-arabino-hexos-2-ulose-utilizing enzyme, may be sufficient for the biosynthesis of cortalcerone from glucose in vivo. The D-arabino-hexos-2-ulose-utilizing enzyme dehydrates certain aldosuloses and has been named aldos-2-ulose dehydratase. The enzyme, which appears to be a dimer of 95-kDa subunits, has been purified 450-fold. Additional properties of aldos-2-ulose dehydratase are described, including its apparent ability to catalyze two different steps in the proposed biosynthetic pathway for cortalcerone.
• Integration of Chemical and Biological Catalysis: Production of Furylglycolic Acid from Glucose via Cortalcerone
  作者：Thomas J. Schwartz、Samuel M. Goodman、Christian M. Osmundsen、Esben Taarning、Michael D. Mozuch、Jill Gaskell、Daniel Cullen、Philip J. Kersten、James A. Dumesic

  DOI：10.1021/cs400593p

  日期：2013.12.6

  Furylglycolic acid (FA), a pseudoaromatic hydroxy-acid suitable for copolymerization with lactic acid, can be produced from glucose via enzymatically derived cortalcerone using a combination of Brønsted and Lewis acid catalysts. Cortalcerone is first converted to furylglyoxal hydrate (FH) over a Brønsted acid site (HCl or Al-containing beta-zeolite), and FH is subsequently converted to FA over a Lewis

  呋喃基乙醇酸（FA）是一种适合与乳酸共聚的假芳族羟基酸，可以使用Brønsted和Lewis酸催化剂的组合，通过酶促衍生的丙酮酸从葡萄糖中制得。首先将Corcercerone在布朗斯台德酸位点（HCl或含Al的β沸石）上转化为呋喃乙二醛水合物（FH），然后在路易斯酸位点（Sn-β沸石）上将FH转化为FA。使用四氢呋喃（THF）作为溶剂在358 K时，将FH转化为FA的选择性高达12％时高达80％。FH的较高转化率导致FA催化FH降解并随后通过沉积使催化剂失活碳质残留物。失活的催化剂可以通过煅烧再生。可以从10％葡萄糖溶液中使用重组蛋白生产Corcercerone从木腐真菌Phanerochaete chrysosporium BKM-F-1767表达吡喃糖2-氧化酶和醛糖-2-纤维素脱水酶的大肠杆菌菌株。在甲醇/水溶剂中，在具有布朗斯台德和路易斯酸位点的含铝Sn-β沸石上，在甲醇/水溶剂中