Microthecin

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: Microthecin
• 英文别名: 6-hydroxy-6-(hydroxymethyl)-2H-pyran-5-one
• 化学式: C₆H₈O₄
• 分子量: 144.127
• InChiKey: FUJVJJBVXLPRQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  10
• 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：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,5-脱水-d-果糖 生成 Microthecin
  参考文献：
  名称：

  红藻 Gracilariopsis lemaneiformis 中微囊藻素的存在及其由 1,5-脱水-d-果糖形成

  摘要：

  Microthecin 是一种从 Gracilariopsis lemaneiformis 中分离出来的吡喃酮，由 1,5-脱水-D-果糖通过两个连续消除反应形成；大概是通过单一酶的作用。

  DOI：

  10.1016/0031-9422(95)00587-0

文献信息

• Formation of 4-deoxy-glycero-hexo-2,3-diulo-furanose from microthecin
  作者：Anders Broberg、Lennart Kenne、Marianne Pedersén

  DOI：10.1016/s0008-6215(97)10045-3

  日期：1998.1

  formed from microthecin [2-hydroxy-2-(hydroxymethyl)-2H-pyran-3(6H)-one] in neutral water solutions by a Michael addition. The compound was determined by NMR spectroscopy, MS and polarimetry to be a racemic mixture of d -and l -forms and existing mainly as two furanosidic C-2 epimers in equilibrium with microthecin. GC–MS analysis showed that 4-deoxy-glycero-hexo-2,3-diulose and microthecin were present

  摘要在中性水溶液中，通过迈克尔加成反应，由微素[2-羟基-2-（羟甲基）-2H-吡喃-3（6H）-一]形成了4-脱氧-己基-2,3-二醛。通过NMR光谱法，MS和旋光法测定该化合物为d-和l-型的外消旋混合物，并且主要以与呋喃霉素平衡的两个呋喃硅C-2差向异构体存在。GC-MS分析表明，红藻Gracilariopsis lemaneiformis的提取物中存在4-deoxy-glycero-hexo-2,3-diulose和microthecin。
• Pyranosone dehydratase from the basidiomycete Phanerochaete chrysosporium: improved purification, and identification of 6-deoxy-d-glucosone and d-xylosone reaction products
  作者：Jiří Gabriel、Jindřich Volc、Petr Sedmera、Geoffrey Daniel、Elena Kubátová

  DOI：10.1007/bf00258142

  日期：1993.7

  produced sugar derivatives. The latter labile compounds were trapped as diphenylhydrazine or o-phenylenediamine derivatives and spectroscopically identified. The analogous D-glucosone dehydration product did not accumulate due to its further transformation. pH optimum of PD I activity was 6.0 and its pH stability was optimal at pH 7-11. The enzyme was sensitive to Me2+ chelating agents and some heavy metal

  在Phanerochaete chrysosporium在搅动条件下的特发生长过程中，吡喃糖氧化酶和吡喃酮脱水酶（醛糖-2-尿糖脱水酶）是在偶联反应中将D-葡萄糖转化为β-吡喃酮丙酮的酶。从真菌的菌丝体提取物中纯化酶，并通过在苯基-琼脂糖和苯基-超糖上的疏水相互作用色谱将彼此分离。解析了两个吡喃酮脱水酶活性峰PD I和PD II。占总脱水酶活性约74％的主要PD I馏分通过Mono Q上的阴离子交换色谱法进一步纯化，以产生明显的纯酶，如SDS-PAGE和Superose 12上的凝胶过滤所判断。等电聚焦表明存在至少五个pI 5.1-5.3的蛋白带，从而表明该蛋白具有微异质性。PD II的pI为5.75。总体PD I纯化为60.7倍，产率为50％。该酶作用于几种osones（糖基蔗糖），优选的底物是D-葡萄糖苷。D-二甲酮和6-脱氧-D-葡糖酮在C-3-C-4脱水，得到相应的5-羟基-2,3-二氧杂als醛（4-deoxy-2
• Process
  申请人：——

  公开号：US20030232417A1

  公开（公告）日：2003-12-18

  The present invention relates to a process for preparing ascopyrone P, or a derivative thereof, said process comprising the steps of: (I) converting a starch-type substrate to 1,5-anhydro-D-fructose with &agr;-1,4-glucan lyase at a pH of from about 3.8 to 7.0; (II) treating said 1,5-anhydro-D-fructose with 1,5-anhydro-D-fructose dehydratase and/or pyranosone dehydratase and optionally ascopyrone P synthase at a pH of from about 5.0 to about 7.5.

  本发明涉及一种制备ascopyrone P或其衍生物的工艺，所述工艺包括以下步骤： (I)用&agr;-1,4-葡聚糖裂解酶在pH值约为3.8至7.0的条件下将淀粉型底物转化为1,5-脱水-D-果糖； (II) 用 1，5-脱水-D-果糖脱水酶和/或吡喃酮脱水酶和可选的 ascopyrone P 合成酶在约 5.0 至约 7.5 的 pH 值下处理所述 1，5-脱水-D-果糖。
• Enzymatic description of the anhydrofructose pathway of glycogen degradation
  作者：Shukun Yu、Charlotte Refdahl、Inge Lundt

  DOI：10.1016/j.bbagen.2004.03.004

  日期：2004.5

  The anhydrofructose pathway describes the degradation of glycogen and starch to metabolites via 1, 5-anhydro-D-fructose (1,5AnFru). The enzyme catalyzing the first reaction step of this pathway, i.e., alpha-1,4-glucan lyase (EC 4.2.1.13), has been purified, cloned and characterized from fungi and red algae in our laboratory earlier. In the present study, two 1,5AnFru metabolizing enzymes were discovered in the fungus Anthracobia melaloma for the formation of ascopyrone P (APP), a fungal secondary metabolite exhibiting antibacterial and antioxidant activity. These are 1,5AnFru dehydratase (AFDH) and ascopyrone tautomerase (APTM). AFDH catalyzed the conversion of 1,5AnFru to ascopyrone M (APM), a compound that has been earlier presumed to occur biologically, while APTM isomerized the APM formed to APP. Both enzymes were purified 400-fold by (NH4)(2)SO4 fractionation, hydrophobic interaction, ion-exchange and gel filtration chromatography. The purified AFDH showed a molecular mass of 98 kDa on SDS-PAGE and 230 kDa by gel filtration. The corresponding values for APTM was 60 and 140 kDa. Spectrophotometric and HPLC methods were developed for the assay of these two enzymes. To confirm that A. melaloma possessed all enzymes needed for conversion of glycogen to APP, an alpha-1,4-glucan lyase from this fungus was isolated and partially sequenced. Based on this work, a scheme of the enzymatic description of the anhydrofructose pathway in A. melaloma was proposed. (C) 2004 Elsevier B.V. All rights reserved.
• The anhydrofructose pathway and its possible role in stress response and signaling
  作者：Shukun Yu、Roland Fiskesund

  DOI：10.1016/j.bbagen.2006.05.007

  日期：2006.9

  Anhydrofructose (AF) pathway describes the catabolism of alpha-1,4-glucans of glycogen, starch and maltosaccharides to various metabolites via the central intermediate AF. The reaction sequence of the pathway consists of more than 10 enzymatic steps. This pathway occurs in certain bacteria, fungi, algae and mammals. In this communication, the AF pathway and its regulatory mechanisms in these organisms are presented and the metabolites of this pathway as antioxidants and antimicrobials in biotic and abiotic stress responses and in carbon starvation signaling are discussed. (c) 2006 Elsevier B.V. All rights reserved.