4-pentenyl 2-acetamido-3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-β-D-glucopyranoside | 134880-20-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-pentenyl 2-acetamido-3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6R)-5-acetamido-4-acetyloxy-6-pent-4-enoxy-3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 134880-20-9
• 化学式: C₃₁H₄₅NO₁₇
• 分子量: 703.695
• InChiKey: AUXDNVQHFOIPCS-CHPZRJSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  49
• 可旋转键数：
  22
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  224
• 氢给体数：
  1
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  4-pentenyl 2-acetamido-3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以94%的产率得到4-pentenyl 2-acetamido-4-O-(β-D-galactopyranosyl)-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  用于监测 α1,3-岩藻糖基转移酶 IX 活性的荧光标记底物

  摘要：

  岩藻糖基化通常是聚糖生物合成的最后一个过程。由此产生的聚糖参与多种生物过程，如细胞粘附、炎症或肿瘤转移。岩藻糖基转移酶催化从活化的供体分子 GDP-β- L转移岩藻糖残基-岩藻糖到各种受体分子。然而，大多数岩藻糖基转移酶仍然缺乏有关反应过程的详细信息。在这项工作中，我们监测了 α1,3-岩藻糖基转移酶的活性。对于供体和受体底物，荧光 ATTO 染料的引入是合成的最后一步。随后通过 α1,3-岩藻糖基转移酶将这些底物转化为荧光标记的产物，通过高效薄层色谱结合质谱以及双色荧光互相关光谱进行检查，结果表明两种荧光标记的供体 GDP -β - L-岩藻糖-ATTO 550 和受体N-乙酰乳糖胺-ATTO 647N 被重组人岩藻糖基转移酶 IX 接受，分别为幽门螺杆菌α1,3-岩藻糖基转移酶。荧光互相关光谱分析允许对酶促反应的进程进行快速和通用的估计，因此该方法可用作研究岩藻糖基转移酶反应的替代方法。

  DOI：

  10.1002/chem.201302601
• 作为产物：
  描述：

  hexa-O-acetyl-D-lactal 在 三氟甲磺酸三甲基硅酯 、 叠氮基三甲基硅烷 、 碘 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 46.0h， 生成 4-pentenyl 2-acetamido-3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  A convenient access to β-glycosides of N-acetyllactosamine

  摘要：

  Iodoacetoxylation of 3,6-di-0-acetyI-4-0-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol (hexa-O-acetyllactal) and the corresponding hexa-O-benzoyl derivative, gave the alpha-1,2-trans 1-O-acetyl-2-deoxy-2-iodo adducts with high stereoselectivity and good yields. These were treated with an excess of trimethylsilyl azide in the presence of trimethylsilyl trifluoromethanesulfonate affording the corresponding alpha-1,2-trans 2-deoxy-2-iodoglycosyl azides. In the presence of an alcohol, a Staudinger reaction at the anomeric azide ledin situ to an iminophosphorane which rearranged with elimination of iodine at C-2. The aziridine intermediate thus obtained reacted with a suitable alcohol to afford the corresponding lactosamine beta-glycosides. The reaction occurred with double inversion of configuration at C-1 and C-2. Deprotection of the amine functionality and further transformation into the acetamido derivatives could be achieved without isolation of the intermediates. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00263-7

文献信息

• Synthesis of a useful anomeric thioacetate of an N-acetyllactosamine derivative and its application
  作者：Koji Matsuoka、Takumi Ohtawa、Hiroshi Hinou、Tetsuo Koyama、Yasuaki Esumi、Shin-Ichiro Nishimura、Ken Hatano、Daiyo Terunuma

  DOI：10.1016/s0040-4039(03)00697-x

  日期：2003.4

  of an N-acetyllactosamine derivative was efficiently synthesized in high yield from the known 2-azido glycosyl chloride using thioacetic acid as a convenient reagent. The synthesis involved not only an SN2 replacement of the chloride by a carbothiolate anion but also a reductive acetamidation of the azide group. Applications of the thioacetate for glycosidation were demonstrated to provide both O- and

  使用硫代乙酸作为方便试剂，从已知的2-叠氮基糖基氯高效高产率地合成了N-乙酰基乳糖胺衍生物的新型异头β-硫代乙酸酯。该合成不仅涉及用硫代硫酸根阴离子对氯化物进行的S N 2取代，而且涉及叠氮化物基团的还原性乙酰胺化。已证明将硫代乙酸酯用于糖苷化可以以高收率提供O-和S-糖苷。此外，两种中间体都产生了包括硫糖苷键的一类新的糖簇。
• Specific crosslinking of cell adhesive molecules by heterobifunctional glycopeptide synthesised on the basis of chemoenzymatic strategy
  作者：Shin-Ichiro Nishimura、Masao Matsuda、Hidemitsu Kitamura、Takashi Nishimura

  DOI：10.1039/a904362d

  日期：——

  Heterobifunctional glycopeptide 1 composed of Neu5Acα-(2→3)Galβ(1→4)[Fucα(1→3)]GlcNAc (sialyl Lewisx) and Lys-Gly-Arg-Gly-Asp-Ser (KGRGDS) having specific activity to bind concurrently with two different types of cell adhesive molecules such as selectins and integrins was synthesised on the basis of a combined chemical and enzymatic strategy.

  异双功能糖肽1由Neu5Acα-(2→3)Galβ(1→4)[Fucα(1→3)]GlcNAc（唾液酸Lewisx）和Lys-Gly-Arg-Gly-Asp-Ser（KGRGDS）组成，具有同时与两种不同类型细胞粘附分子（如选择素和整合素）结合的特定活性，基于综合的化学与酶促策略合成。
• Heterobifunctional Ligands:  Practical Chemoenzymatic Synthesis of a Cell Adhesive Glycopeptide That Interacts with Both Selectins and Integrins
  作者：Masao Matsuda、Shin-Ichiro Nishimura、Fumio Nakajima、Takashi Nishimura

  DOI：10.1021/jm000295r

  日期：2001.3.1

  modulator of cellular recognition is described. A nonnatural glycopeptide 1 composed of sialyl Lewis x and Lys-Gly-Arg-Gly-Asp-Ser that interacts with both selectins and integrins has been systematically synthesized by combined chemical and enzymatic strategy. It is suggested that glycopeptide 1 showed much higher affinity with P-selectin (K(a) = 6.6 x 10(7) M(-1)) and E-selectin (K(a) = 4.5 x 10(5) M(-1))

  作为一种新型的细胞识别调节剂，描述了一种具有独特特性的细胞黏附糖肽的有效合成方法。已通过化学和酶联策略系统地合成了由唾液酸化的路易斯x和Lys-Gly-Arg-Gly-Asp-Ser组成的，与选择素和整联蛋白相互作用的非天然糖肽1。建议糖肽1与P-选择素（K（a）= 6.6 x 10（7）M（-1））和E-选择素（K（a）= 4.5 x 10（5）M（ -1））。该化合物还比四肽Arg-Gly-Asp-Ser更有效地抑制了人类整联蛋白beta（1）及其单克隆抗体之间的特异性相互作用。有趣的是 表面等离子体共振分析表明，这种异双功能糖肽具有同时与P-选择蛋白和整联蛋白β（1）形成稳定复合物的能力。还建议该活性可以作为细胞迁移模型用于抑制整联蛋白介导的活化的辅助T细胞对胶原包被的板的粘附。这些结果表明碳水化合物和多肽的不同生物学功能的化学酶杂交策略是设计有效的糖缀合物作为抗炎和抗癌转移试剂的新