1,5-anhydro-4-deoxy-D-glycero-hex-1-en-3-ulose | 68732-99-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 1,5-anhydro-4-deoxy-D-glycero-hex-1-en-3-ulose
• 英文别名: Ascopyrone P；(2S)-5-hydroxy-2-(hydroxymethyl)-2,3-dihydropyran-4-one
• CAS: 68732-99-0
• 化学式: C₆H₈O₄
• 分子量: 144.127
• InChiKey: ZXCYXCIWKAILMP-BYPYZUCNSA-N

物化性质

• 熔点：
  92-94 °C
• 沸点：
  287.0±40.0 °C(Predicted)
• 密度：
  1.429±0.06 g/cm3(Predicted)

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 在 盐酸 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 40.5h， 生成 1,5-anhydro-4-deoxy-D-glycero-hex-1-en-3-ulose
  参考文献：
  名称：

  A new chemical synthesis of Ascopyrone P from 1,5-anhydro-d-fructose

  摘要：

  The naturally occurring antioxidant Ascopyrone P (1,5-anhydro-4-deoxy-D-glycero-hex-1-en-3-ulose, 1) was prepared from the rare sugar 1,5-anhydroD-fructose (AF, 3) in three steps in an overall yield of 36%. Thus, acetylation of 3 afforded the enolone 3,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-3-en-2-ulopyranose (4), which could be isomerised to 2,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-1-ene-3-ulose (6). Deacetylation of 6 under mild conditions gave crystalline Ascopyrone P (1). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.037

文献信息

• Anti-oxidant
  申请人：——

  公开号：US20020051840A1

  公开（公告）日：2002-05-02

  The present invention provides an anti-oxidant composition comprising a cyclic compound having formula I or a derivative thereof, wherein R 1 and R 2 are indepednetly selected from —OH, ═O, wherein R 3 is a substituent comprising an —OH group; and wherein R 4 and R 5 are other than H; with the proviso that the compound is other than ascorbic acid.

  本发明提供一种抗氧化剂组合物，包括具有式I或其衍生物的环状化合物，其中R1和R2独立地选自—OH，═O，其中R3是含有—OH基团的取代基；且其中R4和R5不同于氢；但化合物不包括抗坏血酸。
• Antimicrobial agent
  申请人：——

  公开号：US20030203963A1

  公开（公告）日：2003-10-30

  The present invention provides an antimicrobial composition for use against a micro-organism selected for Listeria, Salmonella, Bacillus, Saccharomyces, Pseudomonas, Clostridium, Lcatobacillus, Brochothrix, Micrococcus, Yersinia, Enterobacter and Zygosaccharomyces, said composition comprising a cyclic compound having Formula (I), or a derivative thereof, wherein R 1 and R 2 are independently selected from —OH, ═O, and OR′, wherein R′ is H or —COR″, and R″ is C 1-10 alkyl; wherein R 3 is a substituent comprising an OH-group, wherein R 4 and R 5 are each independently selected from a hydrocarbyl group, H, OH or ═O, or represent a bond with an adjacent atom on the ring of the cyclic compound. The invention further relates to a process preventing and/or inhibiting the growth of, and/or killing, micro-organisms in a material, and the use of a cyclic compound having Formula (I).

  本发明提供了一种抗微生物组合物，用于对抗选自李斯特菌、沙门氏菌、芽孢杆菌、酵母菌、假单胞菌、梭菌、Lcatobacillus、Brochothrix、微球菌、耶尔森菌、肠杆菌和Zygosaccharomyces的微生物，所述组合物包含具有式（I）的环状化合物或其衍生物，其中R 1 和 R 2 独立选自-OH、═O 和 OR′，其中 R′是 H 或-COR″，R″是 C 1-10 烷基；其中 R 3 是由 OH 基团组成的取代基，其中 R 4 和 R 5 各自独立地选自烃基、H、OH 或 ═O，或代表与环状化合物环上相邻原子的键。本发明还涉及一种防止和/或抑制材料中微生物生长和/或杀死微生物的工艺，以及具有式（I）的环状化合物的用途。
• 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。
• ASCOPYRONE P: CHEMICAL SYNTHESIS FROM d-GLUCOSE
  作者：S. Andersen、H. Jensen、S. Yu

  DOI：10.1081/car-120016855

  日期：——

  The pyranone, 1,5-anhydro-4-deoxy-D-glycero-hex-1-en-3-ulose (1) (ascopyrone P), has been synthesised in eight steps from D-glucose. The key steps were deacetylation of 3,6-di-O-acetyl-1,5-anhydro-D-glycero-hex-3-en-2-ulose (8) to give isomers and hydrates of 1,5-anhydro-4-deoxy-D-glycero-hex-3-en-2-ulose (9). Isomerisation of this mixture afforded 1,5-anhydro-4-deoxy-D-glycero-hex-1-en-3-ulose (1) (ascopyrone P) in a moderate yield.
• 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.