1,2,3,4-四-O-乙酰基-6-叠氮基-6-脱氧Α-D吡喃半乳糖 | 73108-24-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 1,2,3,4-四-O-乙酰基-6-叠氮基-6-脱氧Α-D吡喃半乳糖
• 英文名称: 1,2,3,4-tetra-O-acetyl-6-azido-6-deoxy-α-D-galactopyranose
• 英文别名: 6-azido-6-deoxy-1,2,3,4-tetra-O-acetyl-D-galactopyranose；1,2,3,4-Tetra-O-acetyl-6-azido-6-desoxy-α-D-galaktopyranose；1,2,3,4-Tetra-O-acetyl-6-azido-6-deoxy-alpha-D-galactopyranose；[(2R,3S,4S,5R,6R)-4,5,6-triacetyloxy-2-(azidomethyl)oxan-3-yl] acetate
• CAS: 73108-24-4
• 化学式: C₁₄H₁₉N₃O₉
• 分子量: 373.32
• InChiKey: LFQWTDKRDROWBN-HTOAHKCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  129
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1,2,3,4-四-O-乙酰基-6-叠氮基-6-脱氧Α-D吡喃半乳糖 在 4 A molecular sieve 、 乙酸肼 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 5-O-(6"-azido-2",3",4"-tri-O-acetyl-6"-deoxy-β-D-galactopyranosyl)-1,3,2',6'-tetraazido-6,3',4'-tri-O-benzyl neamine
  参考文献：
  名称：

  Pyranmycins, a Novel Class of Aminoglycosides with Improved Acid Stability:  The SAR of d-Pyranoses on Ring III of Pyranmycin

  摘要：

  The synthesis of a novel class of aminoglycosides, pyranmycins, is reported along with the structure activity relationship (SAR) of their antibacterial activity against Escherichia coli. Two pyranmycins show prominent activity (9 muM). Pyranmycins also manifest superior stability in acidic media. The SAR information will lead to the future designs of pyranmycin against drug resistant bacteria.

  DOI：

  10.1021/ol0269042
• 作为产物：
  描述：

  乙酸酐 、 6-azido-6-deoxy-D-galactopyranose 在 三氟化硼乙醚 作用下， 反应 0.25h， 以90%的产率得到1,2,3,4-四-O-乙酰基-6-叠氮基-6-脱氧Α-D吡喃半乳糖
  参考文献：
  名称：

  6-Azido d-galactose transfer to N-acetyl-d-glucosamine derivative using commercially available β-1,4-galactosyltransferase

  摘要：

  A new strategy to tag glycoproteins carrying terminal GlcNAc was developed using commercially available bovine beta-1,4-galactosyltransferase (Ga1T) and UDP-6-azidogalactose. The azide function was then allowed to react via a biotinylated Staudinger-Bertozzi probe demonstrating the usefulness of such a procedure to tag any glycoprotein possessing a N-acetylglucosamine terminal residue from any type of cell lysate. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.02.018

文献信息

• 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。
• Design, synthesis and the effect of 1,2,3-triazole sialylmimetic neoglycoconjugates on Trypanosoma cruzi and its cell surface trans-sialidase
  作者：Vanessa L. Campo、Renata Sesti-Costa、Zumira A. Carneiro、João S. Silva、Sergio Schenkman、Ivone Carvalho

  DOI：10.1016/j.bmc.2011.11.022

  日期：2012.1

  This work describes the synthesis of a series of sialylmimetic neoglycoconjugates represented by 1,4-disubstituted 1,2,3-triazole-sialic acid derivatives containing galactose modified at either C-1 or C-6 positions, glucose or gulose at C-3 position, and by the amino acid derivative 1,2,3-triazole fused threonine-3-O-galactose as potential TcTS inhibitors and anti-trypanosomal agents. This series was

  这项工作描述了一系列由1,4-二取代的1,2,3-三唑-唾液酸衍生物代表的一系列唾液酸模拟新糖缀合物的合成，这些衍生物包含在C-1或C-6位置修饰的半乳糖，在C-3处的葡萄糖或果糖位置，并由氨基酸衍生物1,2,3-三唑稠合的苏氨酸-3 - O-半乳糖作为潜在的TcTS抑制剂和抗锥蛋白药物。该系列是通过叠氮基官能化糖1-N 3 -Gal（商业），6-N 3 -Gal，3-N 3-的Cu（I）催化的叠氮化物-炔烃环加成反应（“点击化学”）获得的。 Glc和3-N 3 -Gul与相应的基于炔烃的2-丙炔基唾液酸，以及通过氨基酸N之间的点击化学反应具有3 - O-丙炔基-GalOMe的3 -ThrOBn。所述1,2,3-三唑连接的唾液酸-6- ö半乳糖和唾液酸吡喃半乳糖苷表现出较高的克氏锥虫 反-sialidase（TCTS）抑制活性为1.0毫米（约90％），而只有前者显示相关的杀锥虫活性（IC 50
• MODIFIED CARBOHYDRATE PROCESSING ENZYME
  申请人：Davis Benjamin G.

  公开号：US20090181444A1

  公开（公告）日：2009-07-16

  A modified polypeptide having carbohydrate processing enzymatic activity is provided, said polypeptide comprising an amino acid sequence selected from: (a) the amino acid sequence of SEQ ID NO:2 comprising a mutation in at least one of W433, E432 and M439; (b) the amino acid sequence of an enzyme of glycosyl hydrolase family 1, comprising at least one mutation at an amino acid residue equivalent to W433, E432 or M439 of SEQ ID NO:2; and (c) a variant of (a) or (b) having carbohydrate processing enzymatic activity and comprising at least one amino acid mutation at a position equivalent to W433, E432 or M439 of SEQ ID NO:2.

  提供一种具有碳水化合物加工酶活性的改性多肽，该多肽包括以下氨基酸序列之一：(a) SEQ ID NO: 2的氨基酸序列，其中至少有一个W433、E432和M439突变；(b) 包括至少一个氨基酸残基等同于SEQ ID NO:2的W433、E432或M439的糖基水解酶家族1酶的氨基酸序列；以及(c) 具有碳水化合物加工酶活性的(a)或(b)的变体，其中包括至少一个氨基酸突变位于等同于SEQ ID NO:2的W433、E432或M439的位置。
• Gyoergydeak, Zoltan; Szilagyi, Laszlo, Liebigs Annalen der Chemie, 1987, p. 235 - 242
  作者：Gyoergydeak, Zoltan、Szilagyi, Laszlo

  DOI：——

  日期：——
• US7572604B2
  申请人：——

  公开号：US7572604B2

  公开（公告）日：2009-08-11