N-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-gluco-pyranosyl)azidoacetamide | 73982-46-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-gluco-pyranosyl)azidoacetamide
• 英文别名: [(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-[(2-azidoacetyl)amino]oxan-2-yl]methyl acetate
• CAS: 73982-46-4
• 化学式: C₁₆H₂₃N₅O₉
• 分子量: 429.387
• InChiKey: SVNPCZLBESMJCT-JPIRQXTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  161
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  N-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-gluco-pyranosyl)azidoacetamide 在 palladium on activated charcoal 、 氢气 、 三乙胺 、 mercury dichloride 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 4.5h， 生成
  参考文献：
  名称：

  胍基糖缀合物作为 GlcβArg 类似物的合成

  摘要：

  β-葡萄糖基与精氨酸 (Arg) 的胍基连接存在于淀粉原蛋白中，淀粉原蛋白是一种来自甜玉米的糖蛋白。这种连接是由蛋白质的罕见N-糖基化形成的。通过含有游离氨基的完全乙酰化糖单元与双 Boc-硫脲的反应，合成了不寻常的N-糖苷键 (GlcβArg)类似物，在糖基残基和胍部分之间具有乙酰氨基或三唑间隔基。在本研究期间还实现了具有酰胺接头的N-葡糖基精氨酸的合成。该方法还扩展到阳离子糖脂的合成。

  DOI：

  10.1007/s10719-013-9480-z
• 作为产物：
  描述：

  2-乙酰氨基-1-氨基-1,2-二脱氧-beta-D-吡喃葡萄糖 在 sodium azide 、 Na β-zeolite 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 36.0h， 生成 N-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-gluco-pyranosyl)azidoacetamide
  参考文献：
  名称：

  Synthesis ofN‐(β‐Glycopyrano‐syl)azidoacetamides

  摘要：

  N-(beta-Glycopyranosyl)azidoacetamides, mimetics of the widely distributed GlcNAc-Asn linkage in glycoproteins, have been synthesized in good yields starting from beta-glycopyranosylamines in four steps involving selective N-chloroacetylation, peracetylation catalyzed by Na beta-zeolite, displacement of the Cl group by NaN3 in aqueous acetone, and Zemplen de-O-acetylation.

  DOI：

  10.1081/car-200049402

文献信息

• Glycosyl triazoles as novel insect β-N-acetylhexosaminidase OfHex1 inhibitors: Design, synthesis, molecular docking and MD simulations
  作者：Lili Dong、Shengqiang Shen、Wei Chen、Huizhe Lu、Dongdong Xu、Shuhui Jin、Qing Yang、Jianjun Zhang

  DOI：10.1016/j.bmc.2018.11.032

  日期：2019.6

  furnacalis (Guenée) and inhibition of this enzyme has been considered a promising strategy for the development of eco-friendly pesticides. In this article, based on the structure of the catalytic domains of OfHex1, a series of novel glycosyl triazoles were designed and synthesized via Cu-catalyzed azide-alkyne [3+2] cycloaddition reaction. To investigate the potency and selectivity of these glycosyl triazoles

  昆虫酶GH20β-N-乙酰基-d-己糖胺酶OfHex1代表在农业害虫Ostrinia furnacalis（Guenée）中发现的一种重要的几丁质分解酶，对这种酶的抑制被认为是开发环保农药的一种有前途的策略。本文基于OfHex1催化结构域的结构，设计并通过Cu催化的叠氮化物-炔烃[3 + 2]环加成反应合成了一系列新型糖基三唑。为了研究这些糖基三唑的效力和选择性，研究了对OfHex1和HsHexB（人β-N-乙酰基己糖胺酶B）的抑制活性。特别地，化合物17c（OfHex1，Ki ＝28.68μM； HsHexB，Ki＞100μM）显示出对OfHex1的合适的活性和选择性。此外，使用分子对接和MD模拟研究了OfHex1对17c的可能抑制机制。结构-活性关系结果以及形成的结合模式可能为新型OfHex1抑制剂的进一步开发提供有希望的见识。
• Synthesis and biological activity of some 1-N-substituted 2-acetamido-2-deoxy-β-d-glycopyranosylamine derivatives and related analogs
  作者：Brajeswar Paul、Ralph J. Bernacki、Walter Korytnyk

  DOI：10.1016/s0008-6215(00)85318-5

  日期：——

  adenocarcinoma TA3, leukemia L1210, or leukemia P-288 cells at 1-0.01 mM concentration in vitro. Some of these derivatives were less active after O-deacetylation. Analogs of 1 in which NH2-1 was replaced by OH- or OAc-1 were also active on the same cell systems. The growth-inhibitory activity was correlated with inhibition of the incorporation of 2-amino-deoxy-D-glucose and L-leucine into a macromolecular fraction

  2-乙酰氨基-2-脱氧-3,4,6-三-O的几种1-N-取代的衍生物[卤代乙酰基，甘氨酰-，（二甲基）氨基-乙酰基，叠氮基乙酰基，三氟乙酰基和三氟甲基磺酰基-] -乙酰基-β-D-吡喃葡萄糖胺（1）被合成为细胞膜糖缀合物的潜在代谢抑制剂。在体外浓度为1-0.01 mM时，发现几种完全乙酰化的衍生物可以抑制小鼠乳腺腺癌TA3，白血病L1210或白血病P-288细胞的生长。这些衍生物中的一些在O-脱乙酰基之后活性较低。其中NH2-1被OH-或OAc-1取代的类似物1在相同的电池系统上也很活跃。生长抑制活性与2-氨基-脱氧-D-葡萄糖和L-亮氨酸掺入大分子级分的抑制有关。
• Synthesis and characterization of thiourea- and urea-linked glycolipids as low-molecular-weight hydrogelators
  作者：Manoharan Mathiselvam、Duraikkannu Loganathan、Babu Varghese

  DOI：10.1039/c3ra42041h

  日期：——

  hydrogelating ability as compared to thiourea linked glycolipids. The influence of sugar head group and alkyl chain length on the glycolipid’s self-assembly has also been studied. The fibrillar structures of the supramolecular hydrogels have been characterized by scanning electron microscopy (SEM). The thermal properties of the hydrogels formed by urea linked glycolipids have been studied by differential scanning

  通过使糖基氨基乙酰胺与烷基异硫氰酸酯和异氰酸酯反应，已经合成了具有硫脲和脲连接基的新型糖脂作为低分子量胶凝剂。研究了连接基团对其自组装性能的影响。对获得的新糖脂在各种溶剂中的胶凝研究表明，它们是良好的水凝剂。与硫脲连接的糖脂相比，尿素连接的糖脂显示出更好的水凝胶化能力。还研究了糖首基和烷基链长对糖脂自组装的影响。超分子水凝胶的原纤维结构已经通过扫描电子显微镜（SEM）表征。由尿素连接的糖脂形成的水凝胶的热性质已通过差示扫描量热法（DSC）和VT-NMR进行了研究。已经通过小角度（SAXS）和单晶X射线衍射方法研究了分子堆积。
• Synthesis of novel glycolipids derived from glycopyranosyl azides and N-(β-glycopyranosyl)azidoacetamides
  作者：Katuri J.V. Paul、Duraikkannu Loganathan

  DOI：10.1016/j.tetlet.2008.08.073

  日期：2008.10

  A general and expedient method based on a click reaction has been developed for the synthesis of novel glycolipids. The Cu(I) catalyzed [3+2] cycloaddition of several fully acetylated beta- as well as alpha-D-glycopyranosyl azides, including the 1,6-diazide derived from D-glucose, with long chain alkyl propargyl ethers gave the respective 1,4-substituted 1,2,3-triazole derivatives in good yields. Treatment of fully acetylated N-(beta-glycopyranosyl)azidoacetamides under similar conditions with alkyl propargyl ethers afforded the 1,2,3-triazolylacetamido derivatives in fairly good yields. Zemplen de-O-acetylation of all the fully acetylated derivatives furnished the free glycolipids in quantitative yields. (c) 2008 Elsevier Ltd. All rights reserved.