4-deoxy-4-azido-D-xylose | 13144-00-8

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 4-deoxy-4-azido-D-xylose
• 英文别名: 4-azido-4-deoxy-D-xylose；4-azido-D-4-deoxy-xylose；4-azido-ξ-D-4-deoxy-xylopyranose；(3R,4S,5R)-5-azidooxane-2,3,4-triol
• CAS: 13144-00-8
• 化学式: C₅H₉N₃O₄
• 分子量: 175.144
• InChiKey: MRCUMXZQJPAAER-IOVATXLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.26
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  118.68
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-deoxy-4-azido-D-xylose 生成 1,4-二脱氧-1,4-亚氨基阿拉伯糖醇
  参考文献：
  名称：

  NALEWAY, JOHN J.;RAETZ, CHRISTIAN R. H.;ANDERSON, LAURENS, CARBOHYDR. RES., 179,(1988) C. 199-209

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 4-azido-4-deoxy-2,3-O-isopropylidene-α-L-arabinopyranoside 生成 4-deoxy-4-azido-D-xylose
  参考文献：
  名称：

  NALEWAY, JOHN J.;RAETZ, CHRISTIAN R. H.;ANDERSON, LAURENS, CARBOHYDR. RES., 179,(1988) C. 199-209

  摘要：

  DOI：

文献信息

• Synthesis of Modified Aldonic Acids and Studies of Their Substrate Efficiency for Dihydroxy Acid Dehydratase (DHAD)
  作者：G Limberg、G Limberg、J Thiem、J Thiem

  DOI：10.1071/ch9960349

  日期：——

  Modified aldopentonic and aldohexonic acids were synthesized in order to study the electronic requirements for a successful enzymatic conversion into their corresponding 2-keto 3-deoxy analogues by dihydroxy acid dehydratase (DHAD), an enzyme from the biosynthetic pathway of branched chain amino acids. Analytical tests with the novel artificial substrates (18)-(21) and (27) provided evidence that the amount of conversion could be enhanced by replacement of the hydroxy group at C4 of L-arabinonic acid (21) with less electron-withdrawing, ambivalent or electron-donating substituents. Modified aldohexonic acids were no substrates for DHAD, perhaps due to less perfect binding to the active site presumably for steric reasons. For 4-deoxy-L-threo-pentonic acid (18) the enzymatic conversion into 3,4-dideoxy-2-ketopentonic acid (29) by DHAD could be achieved on a preparative scale.

  为了研究支链氨基酸生物合成途径中的二羟基酸脱水酶（DHAD）将其成功酶促转化为相应的 2-酮 3-脱氧类似物的电子要求，我们合成了改良的醛戊酸和醛己酸。用新型人工底物（18）-（21）和（27）进行的分析测试证明，用较少的电子吸收、矛盾或电子供体取代 L-阿拉伯醛酸（21）C4 的羟基，可以提高转化率。修饰的醛己酸不是 DHAD 的底物，这可能是由于与活性位点的结合不够完美，也可能是由于立体原因。对于 4-脱氧-L-苏式戊酸（18），DHAD 可以将其酶转化为 3,4-二脱氧-2-酮戊酸（29）。
• Synthesis of azido-deoxy and amino-deoxy glycosides and glycosyl fluorides for screening of glycosidase libraries and assembly of substituted glycosides
  作者：Hong-Ming Chen、Stephen G. Withers

  DOI：10.1016/j.carres.2018.07.007

  日期：2018.9

  useful tools in the probing of biological systems as well as in the assembly of libraries of derivatives using click chemistry or simple amine coupling approaches. A collection of methylumbelliferyl glycosides of various azido- and amino-deoxy sugar derivatives of glucose, galactose and xylose was synthesised via azide displacement of the corresponding triflate derivatives and subsequent modification.

  叠氮化物和胺取代的糖在探测生物系统以及使用点击化学或简单的胺偶联方法组装衍生物库中可能是有用的工具。通过叠氮化物置换相应的三氟甲磺酸衍生物并随后进行修饰，合成了葡萄糖，半乳糖和木糖的各种叠氮基和氨基脱氧糖衍生物的甲基伞形糖苷苷。这些化合物将在高通量筛选中用作底物，以鉴定可加工此类修饰糖的糖苷酶。还合成了每种修饰糖的α-糖基氟衍生物，以用作衍生自筛选中鉴定的酶的糖合酶底物。
• The Identification of Perillyl Alcohol Glycosides with Improved Antiproliferative Activity
  作者：Nitin S. Nandurkar、Jianjun Zhang、Qing Ye、Larissa V. Ponomareva、Qing-Bai She、Jon S. Thorson

  DOI：10.1021/jm500870u

  日期：2014.9.11

  A facile route to perillyl alcohol (POH) differential glycosylation and the corresponding synthesis of a set of 34 POH glycosides is reported. Subsequent in vitro studies revealed a sugar dependent antiproliferative activity and the inhibition of S6 ribosomal protein phosphorylation as a putative mechanism of representative POH glycosides. The most active glycoside from this cumulative study (4'-azido-d-glucoside, PG9) represents one of the most cytotoxic POH analogues reported to date.
• Pyrrolodine sugars. Synthesis of 9-(4-acetamido-4-deoxy-.beta.-D-xylofuranosyl)adenine and other derivatives of 4-amino-4-deoxy-D-xylose
  作者：Elmer J. Reist、Linda V. Fisher、Leon Goodman

  DOI：10.1021/jo01283a038

  日期：1967.8
• Identification of the 2-hydroxymethyl-3,4-dihydroxypyrrolidine (or 1,4-dideoxy-1,4-iminopentitol) from and from as the (2R, 3R, 4S)-isomer by the synthesis of its enantiomer.
  作者：D.Wyn C. Jones、Robert J. Nash、E.Arthur Bell、J.Michael Williams

  DOI：10.1016/s0040-4039(00)98635-0

  日期：1985.1