5-叠氮基-5-脱氧-D-果糖 | 94801-02-2

• 物质功能分类: 生物化工 - 糖类化合物 - 单糖
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 5-叠氮基-5-脱氧-D-果糖
• 英文名称: 5-azido-5-deoxy-D-fructopyranose
• 英文别名: 5-azido-5-deoxy-D-fructose；(2R,3S,4R,5R)-5-azido-2-(hydroxymethyl)oxane-2,3,4-triol
• CAS: 94801-02-2
• 化学式: C₆H₁₁N₃O₅
• 分子量: 205.17
• InChiKey: PKWGGYMHQZGSBV-ARQDHWQXSA-N

物化性质

• 熔点：
  113-115°C
• 溶解度：
  甲醇（微溶）、水（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  105
• 氢给体数：
  4
• 氢受体数：
  7

安全信息

• 海关编码：
  2932999099
• 储存条件：
  -20°C 冰箱

反应信息

• 作为反应物：
  描述：

  5-叠氮基-5-脱氧-D-果糖 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 48.0h， 以88%的产率得到Alpha-葡萄糖苷酶
  参考文献：
  名称：

  2,5-二脱氧-2,5-亚氨基-d-甘露糖醇和-d-葡萄糖醇。由5-叠氮基5-脱氧-d-呋喃呋喃糖和-1--1-呋喃呋喃糖分两步进行生物有机合成；作为葡糖苷酶抑制剂的评价及其在酵母中转化酶亲和力纯化和表征中的应用

  摘要：

  摘要葡萄糖异构酶（EC 5.3.1.5）催化5-叠氮基5-脱氧-d-葡萄糖-（7和-1--1-呋喃基葡萄糖（9）分别定量异构化为相应的酮糖5-azido-5-脱氧-d-果糖-吡喃糖（8）和-l-山梨糖醇糖（10）。在木炭上进行钯催化氢化后，果糖衍生物8得到了天然产物和有效的糖苷酶抑制剂2,5-dideoxy- 2,5-亚氨基-d-甘露醇（4），而山梨糖衍生物10则提供2,5-二脱氧-2,5-亚氨基-d-葡萄糖醇（5），这是一种制备非常简单有效的两步合成方法这些生物活性化合物都是来自各种来源的强力抑制剂α-和β-葡萄糖苷酶，d-甘露糖异构体4的活性明显更高。由于其与β-d-果糖呋喃糖的结构关系，化合物4还是来自酵母的非常好的转化酶抑制剂，因此，在固定于氨基己基-琼脂糖上之后，首次将其用于纯化该酶。

  DOI：

  10.1016/0008-6215(93)84155-y
• 作为产物：
  描述：

  [(2R,3S,4R,5R)-5-azido-2,3,4-trihydroxyoxan-2-yl]methyl dihydrogen phosphate 生成 5-叠氮基-5-脱氧-D-果糖
  参考文献：
  名称：

  HUNG, REBECCA R.;STRAUB, JULIE ANN;WHITESIDES, GEORGE M., J. ORG. CHEM., 56,(1991) N2, C. 3849-3855

  摘要：

  DOI：

文献信息

• Chemoenzymatic Preparation of Novel Cyclic Imine Sugars and Rapid Biological Activity Evaluation Using Electrospray Mass Spectrometry and Kinetic Analysis
  作者：Shuichi Takayama、Richard Martin、Jiangyue Wu、Karen Laslo、Gary Siuzdak、Chi-Huey Wong

  DOI：10.1021/ja971695f

  日期：1997.9.1

  and since imines are key intermediates in a variety of cycloadditions, condensations, and nucleophilic additions, they are valuable as versatile synthetic intermediates for the preparation of novel iminocyclitols and derivatives. An example of such synthetic utility is demonstrated by the synthesis of amino-iminocyclitol 24 via a three-center, two-component Strecker reaction. A novel method for rapidly

  环状亚胺糖是通过一种新的化学酶促策略制备的，其中通过酶促醛醇反应构建的叠氮糖在酸性条件下氢化。发现这些环状亚胺糖是糖加工酶的有效抑制剂，这些酶对多种糖苷酶的 Ki 值在纳摩尔和微摩尔范围内。与它们完全氢化的对应物相比，环状亚胺糖通常对所测试的糖苷酶表现出相当或更好的抑制作用。由于这些环状亚胺很容易获得，并且由于亚胺是各种环加成、缩合和亲核加成的关键中间体，因此它们作为用于制备新型亚氨基环醇和衍生物的通用合成中间体是有价值的。通过三中心、两组分 Strecker 反应合成氨基-亚氨基环醇 24 证明了这种合成效用的一个例子。一种使用电喷雾快速筛选糖苷酶抑制剂的新方法...
• .alpha.-Amino aldehyde equivalents as substrates for rabbit muscle aldolase: synthesis of 1,4-dideoxy-D-arabinitol and 2(R),5(R)-bis(hydroxymethyl)-3(R),4(R)-dihydroxypyrrolidine
  作者：Rebecca R. Hung、Julie Ann Straub、George M. Whitesides

  DOI：10.1021/jo00012a015

  日期：1991.6

  This work examined the application of rabbit muscle aldolase (RAMA) to stereospecific carbon-carbon bond formation in the preparation of carbohydrates containing amino groups. Several alpha-amino aldehyde equivalents were evaluated as substrates for RAMA and for their synthetic utility in transformations following the aldol reaction. This methodology is illustrated by the syntheses of the pyrrolidine alkaloids 1,4-dideoxy-D-arabinitol and 2(R),5(R)-bis(hydroxymethyl)-3(R), 4(R)-dihydroxypyrrolidine. The kinetic resolution of racemic aldehydes by RAMA and mild methods for transforming the amino equivalents into the desired amines are discussed briefly.
• Synthesis of a novel α-glucoside of the powerful glucosidase inhibitor 2,5-dideoxy-2,5-imino-d-mannitol via enzymatic glucosylation of 5-azido-5-deoxy-d-fructopyranose
  作者：Karl Dax、Michael Ebner、Roland Peinsipp、Arnold E. Stütz

  DOI：10.1016/s0040-4039(96)02281-2

  日期：1997.1

  Regio- and stereoselective enzymatic glucosylation of 5-azido-5-deoxy-D-fructopyranose with the aid of commerically available alpha-glucosidase from yeast allows easy access to the corresponding 4-O-alpha-D-glucopyranosyl derivative of this non-natural ketose. This disaccharide gives, in one step, access to 2,5-dideoxy-3-O-alpha-D-glucopyranosyl-2,5-imino-D-mannitol. Copyright (C) 1996 Elsevier Science Ltd
• Nickel(II)-Catalysed Transformations of 5-Azido-5-deoxy-<scp>d</scp>-glucofuranose and of 5-Azido-5-deoxy-<scp>l</scp>-idofuranose
  作者：Philipp Hadwiger、Andreas Lechner、Arnold E. Stütz

  DOI：10.1080/07328309808002325

  日期：1998.3.1

  Nickel(II) catalysed isomerisation reactions of C-5 modified derivatives of D-glucose as well as L-idose were investigated. 5-Azido-5-deoxy-D-glucofuranose was successfully isomerised into the corresponding D-manno epimer in good yields. Contrasting this result, in the case of the 5-modified L-idofuranose probed, no evidence for successful epimerisation at C-2 could be found. However, this sugar was quantitatively rearranged into the corresponding L-sorbopyranose. Upon extended reaction periods, the latter underwent degradation to give the coresponding 4-modified methyl L-xylonate.
• 2,5-dideoxy-2,5-imino-d-mannitol and -d-glucitol. Two-step bio-organic syntheses from 5-azido-5-deoxy-d-glucofuranose and -l-idofuranose; evaluation as glucosidase inhibitors and application in affinity purification and characterisation of invertase from yeast
  作者：Günter Legler、Annette Korth、Andreas Berger、Christian Ekhart、Günther Gradnig、Arnold E. Stütz

  DOI：10.1016/0008-6215(93)84155-y

  日期：1993.12

  5-dideoxy-2,5-imino- d -glucitol ( 5 ). This represents a preparatively very simple and efficient two-step synthesis of these biologically active compounds. Both are strong inhibitors of α- and β-glucosidases from various sources, the d - manno -isomer 4 being distinctly more active. Because of its structural relationship with β- d -fructofuranose, compound 4 is also a very good inhibitor of invertase from

  摘要葡萄糖异构酶（EC 5.3.1.5）催化5-叠氮基5-脱氧-d-葡萄糖-（7和-1--1-呋喃基葡萄糖（9）分别定量异构化为相应的酮糖5-azido-5-脱氧-d-果糖-吡喃糖（8）和-l-山梨糖醇糖（10）。在木炭上进行钯催化氢化后，果糖衍生物8得到了天然产物和有效的糖苷酶抑制剂2,5-dideoxy- 2,5-亚氨基-d-甘露醇（4），而山梨糖衍生物10则提供2,5-二脱氧-2,5-亚氨基-d-葡萄糖醇（5），这是一种制备非常简单有效的两步合成方法这些生物活性化合物都是来自各种来源的强力抑制剂α-和β-葡萄糖苷酶，d-甘露糖异构体4的活性明显更高。由于其与β-d-果糖呋喃糖的结构关系，化合物4还是来自酵母的非常好的转化酶抑制剂，因此，在固定于氨基己基-琼脂糖上之后，首次将其用于纯化该酶。