lactosyl azide | 30854-62-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: lactosyl azide
• 英文别名: hepta-O-acetyl-β-lactosyl azide；β-D-lactosyl azide；4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2,3,6-tri-Oacetyl-β-D-glucopyranosyl azide；2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl azide；2,3,6,2',3',6'-Hepta-O-acetyl-B-lactosyl azide；[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-6-azido-3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 30854-62-7
• 化学式: C₂₆H₃₅N₃O₁₇
• 分子量: 661.574
• InChiKey: JFCQZWVIHHPJTD-LTSQYKSLSA-N

物化性质

• 熔点：
  69-70 °C

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  46
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  226
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  lactosyl azide 在 吡啶 、 4-二甲氨基吡啶 、 palladium on activated charcoal 、 氢气 作用下， 以 二氯甲烷 为溶剂， 20.0~35.0 ℃ 、4.0 MPa 条件下， 反应 25.0h， 生成 4-oxo-4-[(2,3,6-tri-O-acetyl-4-O-2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl-β-D-glucopyranosyl)amino]butanoic acid
  参考文献：
  名称：

  Synthesis and Biological Evaluation of an Orally Active Glycosylated Endomorphin-1

  摘要：

  The endogenous opioid peptide endomorphin-1 (1) was modified by attachment of lactose to the N-terminus via a succinamic acid spacer to produce compound 2. The carbohydrate modification significantly improved the metabolic stability and membrane permeability of 2 while retaining mu-opioid receptor binding affinity and agonist activity. Analogue 2 produced dose-dependent antinociceptive activity following intravenous administration in a chronic constriction injury (CCI) rat model of neuropathic pain with an ED50 of 8.3 (+/- 0.8) mu mol/kg. The corresponding ED50 for morphine was 2.6 (+/- 1.4) mu mol/kg. Importantly, compound 2 produced dose-dependent pain relief after oral administration in CCI rats (ED50 = 19.6 (+/- 1.2) mu mol/kg), which was comparable with that of morphine (ED50 = 20.7 (+/- 3.6) mu mol/kg). Antineuropathic effects of analogue 2 were significantly attenuated by pretreatment of animals with the opioid antagonist naloxone, confirming opioid receptor-mediated analgesia. In contrast to morphine, no significant constipation was produced by compound 2 after oral administration.

  DOI：

  10.1021/jm300418d
• 作为产物：
  描述：

  hepta-O-acetyl-β-maltosyl chloride 在 sodium azide 作用下， 以 水 、 丙酮 为溶剂， 生成 lactosyl azide
  参考文献：
  名称：

  探索磺酰胺部分生物立体取代羧酰胺对N-糖苷扭转和分子组装的影响：作为N-糖蛋白连接区类似物的N-（β-D-糖基）磺酰胺的合成和X射线晶体学研究

  摘要：

  在所有真核生物中，N-糖蛋白连接区的成分，即2-乙酰氨基-2-脱氧-β - D-吡喃葡萄糖（GlcNAc）和天冬酰胺（Asn）都是保守的。为了更好地理解大自然选择GlcNAcβAsn作为连接区组成以及分子间和分子内碳水化合物与蛋白质的相互作用，对连接区构象进行详细的系统结构研究是必不可少的。较早的几种N-（β-甘露糖基糖基）烷基酰胺的晶体学研究表明，糖苷部分的结构变化比糖苷配基部分更受N-糖苷扭转ϕ N的影响。探索磺酰胺部分生物等位取代羧酰胺基对小鼠的影响N糖苷扭转以及分子组装过程中，合成了几种糖基甲磺酰胺和糖基氯甲磺酰胺作为N糖蛋白连接区的类似物，并且已经解析了其中7种化合物的晶体结构。对这一系列晶体结构以及相应的烷酰胺基衍生物的晶体结构的比较分析表明，N糖苷扭转to N并没有显着改变。与其他磺酰胺基类似物相比，GlcNAc的甲烷磺酰胺基和氯甲烷磺酰胺基衍生物显示出不同的糖苷配基构象。这

  DOI：

  10.1002/chem.201302018

文献信息

• Synthesis of new asparagine-based glycopeptides for future scanning tunneling microscopy investigations
  作者：Laura Sršan、Thomas Ziegler

  DOI：10.3762/bjoc.16.80

  日期：——

  disaccharides containing glycopeptides were prepared in solution. The applicability of two common peptide coupling reagents, using an orthogonal Fmoc/t-Bu strategy along with acetyl protecting groups for the carbohydrate moiety, was studied. Thus, the prepared libraries of glycopeptides were designed as model systems of cell surfaces for future investigations by combined preparative mass spectroscopy and

  为了研究寡糖和拟肽的生物学功能，在溶液中制备了新的含有糖肽的天冬酰胺基单糖和二糖。使用正交的Fmoc / t- Bu策略以及碳水化合物部分的乙酰基保护基，研究了两种常见的肽偶联剂的适用性。因此，将制备的糖肽文库设计为细胞表面的模型系统，以供将来通过在金属表面上使用软着陆电喷雾束沉积（ES-IBD）的组合制备质谱和扫描隧道显微镜（STM）进行研究。
• First noscapine glycoconjugates inspired by click chemistry
  作者：Kunj B. Mishra、Ram C. Mishra、Vinod K. Tiwari

  DOI：10.1039/c5ra07321a

  日期：——

  A number of novel 7-O-noscapine glycoconjugates have been synthesized starting from noscapine, an alkaloid found in the opium plant, via two successive steps. The first step is a selective 7-O-demethylation of noscapine and the next is a subsequent propargylation which affords 7-O-propargyl noscapine (3) in good yield. The structure was confirmed by extensive spectroscopic data including single crystal

  已经通过两个连续的步骤，从鸦片植物中发现的一种生物碱-诺斯卡汀开始合成了许多新颖的7- O-诺斯卡汀糖缀合物。第一步是Noscapine的选择性7- O-去甲基化，第二步是随后的炔丙基化，以良好的收率得到7- O-炔丙基基Noscapine（3）。通过包括单晶X射线数据在内的大量光谱数据证实了该结构。研究了发达的Noscapine衍生物3与糖基叠氮化物6a–m的1,3-偶极环加成反应，得到了三唑连接的第二代Noscapine类似物，其糖缀合物形式（8a–m ）以增强Noscapine的治疗功效。
• A Generalized Procedure for the One-Pot Preparation of Glycosyl Azides and Thioglycosides Directly from Unprotected Reducing Sugars under Phase-Transfer Reaction Conditions
  作者：Rishi Kumar、Pallavi Tiwari、Prakas R. Maulik、Anup K. Misra

  DOI：10.1002/ejoc.200500646

  日期：2006.1

  Per-O-acetylated glycosyl azides and thioglycosides were prepared in excellent yield directly from unprotected reducing sugars through in situ generation of per-O-acetylated glycosyl bromides by a generalized one-pot procedure under phase-transfer conditions. Stereoselective products were formed with complete inversion at the anomeric centers of the glycosyl bromides to provide a general high-yielding

  过氧乙酰化糖基叠氮化物和硫代糖苷直接从未保护的还原糖通过通用的一锅法在相转移条件下原位生成过氧乙酰化糖基溴化物，以优异的收率制备。在糖基溴化物的异头中心完全反转形成立体选择性产物，为制备 1,2-反式糖基叠氮化物和硫代糖苷提供了一种通用的高产率方法。（© Wiley-VCH Verlag GmbH & Co. KGaA， 69451 德国魏因海姆，2006）
• Synthesis of N-(fluoren-9-ylmethoxycarbonyl)glycopyranosylamine uronic acids
  作者：Laiqiang Ying、Jacquelyn Gervay-Hague

  DOI：10.1016/j.carres.2003.10.018

  日期：2004.1

  The synthesis of 10 N-(fluoren-9-ylmethoxycarbonyl)glycopyranosylamine uronic acids that are amenable to solid-phase synthesis is described. The general synthetic strategy involves initial incorporation of the protected amine, followed by selective TEMPO oxidation of C-6 hydroxyl groups to give the corresponding Fmoc-protected sugar amino acids. Amine incorporation may be accomplished from aminolysis

  描述了适于固相合成的10种N-（氟-9-基甲氧基羰基）甘露糖基氨基糖醛酸的合成。一般的合成策略包括首先引入受保护的胺，然后对C-6羟基进行TEMPO选择性氧化，得到相应的Fmoc保护的糖氨基酸。胺的掺入可通过游离糖的氨解或糖基叠氮化物的还原来完成。该反应可以以多克级进行，从而提供了访问独特单体单元的途径，以便将来将其并入组合文库合成中。
• Iron(iii) chloride as an efficient catalyst for stereoselective synthesis of glycosyl azides and a cocatalyst with Cu(0) for the subsequent click chemistry
  作者：Santosh B. Salunke、N. Seshu Babu、Chien-Tien Chen

  DOI：10.1039/c1cc13370e

  日期：——

  A highly efficient and mild method for azido glycosylation of glycosyl β-peracetates to 1,2-trans glycosyl azides was developed by using inexpensive FeCl3 as the catalyst. In addition, we demonstrated, for the first time, that FeCl3 in combination with copper powder can promote 1,3-dipolar cycloaddition (click chemistry) of azido glycosides with terminal alkynes. Good to excellent yields were obtained with exclusive formation of a single isomer in both glycosyl azidation and subsequent cycloaddition processes.

  一种高效而温和的方法被开发出来，利用廉价的FeCl3作为催化剂，实现了糖基β-过乙酸酯的叠氮糖基化反应，制备了1,2-反式糖基叠氮化合物。此外，我们首次证明了FeCl3与铜粉的组合能够促进叠氮糖基与末端炔烃的1,3-偶极环加成反应（点击化学）。在糖基叠氮化和随后的环加成反应过程中，均获得了良好至优异的产率，并且仅形成单一的异构体。