N4-{O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-α-D-mannopyranosyl-(1->3)-[O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-α-D-mannopyranosyl-(1->6)]-O-β-D-mannopyranosyl-(1->4)-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-(2-acetamido-2-deoxy-β-D-glucopyranosyl)}-L-asparagine | 68418-91-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: N4-{O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-α-D-mannopyranosyl-(1->3)-[O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-α-D-mannopyranosyl-(1->6)]-O-β-D-mannopyranosyl-(1->4)-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-(2-acetamido-2-deoxy-β-D-glucopyranosyl)}-L-asparagine
• 英文别名: 2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1->2)-alpha-D-mannopyranosyl-(1->3)-[2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1->2)-alpha-D-mannopyranosyl-(1->6)]-beta-D-mannopyranosyl-(1->4)-2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1->4)-2-acetamido-N-[(3S)-3-azaniumyl-3-carboxylatopropanoyl]-2-deoxy-beta-D-glucopyranosylamine；(2S)-4-[[(2R,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(2S,3S,4S,5R,6R)-4-[(2S,3S,4S,5S,6R)-3-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2S,3S,4S,5S,6R)-3-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3,5-dihydroxyoxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]amino]-2-azaniumyl-4-oxobutanoate
• CAS: 68418-91-7
• 化学式: C₅₄H₉₀N₆O₃₈
• 分子量: 1431.33
• InChiKey: UPORYLBXQJDYFC-XOEKKIKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -16.9
• 重原子数：
  98
• 可旋转键数：
  27
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  693
• 氢给体数：
  25
• 氢受体数：
  39

反应信息

• 作为反应物：
  描述：

  N4-{O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-α-D-mannopyranosyl-(1->3)-[O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-α-D-mannopyranosyl-(1->6)]-O-β-D-mannopyranosyl-(1->4)-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-(2-acetamido-2-deoxy-β-D-glucopyranosyl)}-L-asparagine 在 jack bean β-N-acetylglucosaminidase 、 BSA 作用下， 反应 120.0h， 以46.8%的产率得到α-Man-(1<*>6)<*> α-Man-(1<*>3)<*> β-Man-(1<*>4)-β-GlcNAc-(1<*>4)-β-GlcNAc<*>Asn
  参考文献：
  名称：

  来自 Platypodium elegans 的凝集素，对不对称复合 N-聚糖具有不同寻常的特异性和亲和力。

  摘要：

  已经在 Platypodium elegans 的种子中检测到了对甘露糖和葡萄糖具有特异性的凝集素活性，Platypodium elegans 是一种来自 Dalbergieae 部落的豆科植物。Platypodium elegans 凝集素A基因已被克隆，所得261个氨基酸的蛋白质属于豆科植物凝集素家族，与同一部落的Pterocarpus angolensis凝集素相似。重组凝集素已在大肠杆菌中表达并从包涵体中重新折叠。通过聚糖阵列的特异性分析证明了对具有不对称分支的复杂类型 N-聚糖的非常不寻常的偏好。在 N-聚糖的 6 臂上优选由一个甘露糖残基组成的短分支，而在 3 臂上由 GlcNAc、Gal 和 NeuAc 延伸是有利的。使用半合成方法制备的对称和不对称 Asn 连接的七糖，通过微量热法获得了亲和力。为这两种配体获得了与 K(d) 4.5 妈妈的强亲和力。Platypodium elegans

  DOI：

  10.1074/jbc.m112.375816
• 作为产物：
  描述：

  N4-{O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-α-D-mannopyranosyl-(1->3)-[O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-α-D-mannopyranosyl-(1->6)]-O-β-D-mannopyranosyl-(1->4)-O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)}-N2-benzyloxycarbonyl-L-asparagine benzyl ester 在 钯 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以95.1%的产率得到N4-{O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-α-D-mannopyranosyl-(1->3)-[O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-α-D-mannopyranosyl-(1->6)]-O-β-D-mannopyranosyl-(1->4)-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-(2-acetamido-2-deoxy-β-D-glucopyranosyl)}-L-asparagine
  参考文献：
  名称：

  化学酶法合成与天冬酰胺连接的唾液酸化双触角N-聚糖。

  摘要：

  许多糖蛋白的局部结构，带有复杂类型的十一糖N-聚糖（Neu5Ac（alpha 2-6）Gal（beta 1-4）GlcNAc（beta 1-2）Man alpha 1-3）[Neu5Ac（alpha通过全合成获得2-6）Gal（β1-4）GlcNAc（β1-2）Man（α1-6）] Man（β1-4）GlcNAc（β1-4）GlcNAc-Asn）。作为起始原料，使用化学合成的双触角七糖叠氮化物，该三叠氮化物以三步顺序脱保护，产率高。异头叠氮化物的还原是用丙二酚在甲醇-乙基二异丙胺中完成的。糖基胺与活化的天冬氨酸的偶联产生了苄基保护的天冬酰胺缀合物。在除去六个苄基官能团之后，所得的游离七糖天冬酰胺在寡糖部分中酶促地拉长。使用beta-1

  DOI：

  10.1016/s0008-6215(97)10056-8

文献信息

• Synthesis of an Fmoc-Asn-heptasaccharide building block and its application to chemoenzymatic glycopeptide synthesis
  作者：Stefano Mezzato、Carlo Unverzagt

  DOI：10.1016/j.carres.2010.02.022

  日期：2010.7

  heptasaccharide asparagine building block beta-GlcNAc-(1-->2)-alpha-Man-(1-->3)-[beta-GlcNAc-(1-->2)-alpha-Man-(1-->6)]beta -Man-(1-->4)-beta-GlcNAc-(1-->4)-beta-GlcNAc-(Fmoc)Asn was obtained by chemical synthesis. Two flexible strategies were developed with optimized conditions for the simultaneous debenzylation of the sugar and the amino acid part. The heptasaccharide asparagine building block is a partial structure

  Fmoc保护的七糖天冬酰胺构建基块β-GlcNAc-（1-> 2）-alpha-Man-（1-> 3）-β-GlcNAc-（1-> 2）-alpha-Man-（通过化学合成获得1-（6）]β-Man-（1→4）-β-GlcNAc-（1→4）-β-GlcNAc-（Fmoc）Asn。针对糖和氨基酸部分的同时去苄基化，开发了两种具有最佳条件的灵活策略。七糖天冬酰胺的结构单元是许多糖蛋白的部分结构，可用于溶液和固相中的糖肽合成。在这项工作中，七糖天冬酰胺在溶液中被拉长为Fmoc-糖基戊糖肽甲酯。在化学裂解Fmoc基团之后，通过胰凝乳蛋白酶将甲基酯酶促除去。使用beta-（1-> 4）-半乳糖基转移酶和alpha-（2->
• Prompt Chemoenzymatic Synthesis of Diverse Complex-Type Oligosaccharides and Its Application to the Solid-Phase Synthesis of a Glycopeptide with Asn-Linked Sialyl-undeca- and Asialo-nonasaccharides
  作者：Yasuhiro Kajihara、Yasuhiro Suzuki、Naoki Yamamoto、Ken Sasaki、Tohru Sakakibara、Lekh Raj Juneja

  DOI：10.1002/chem.200305115

  日期：2004.2.20

  Using these pure monosialiloligosaccharides enable us to obtain 24 Asn-linked oligosaccharides (100 mg scale) within a few weeks by branch specific exo-glycosidase digestions (alpha-D-neuraminidase, beta-D-galactosidase, N-acetyl-beta-D-glucosaminidase and alpha-D-mannosidase). In addition, solid-phase synthesis of glycopeptide having Asn-linked sialyl-undeca- and asialo-nonasaccharides thus obtained,

  我们在这里描述了从天冬酰胺连接的双天线复合型唾液酸十二糖[（NeuAc-alpha-2,6-Gal-beta-1,4-GlcNAc-beta-1， 2-Man-alpha-1,6 / 1,3-）（2）-Man-beta-1，4-GlcNAc-beta-1,4-GlcNAc-beta-1-asparagine，2]从蛋黄获得。我们的合成策略旨在在制备由酸从2中获得的单唾液酸寡糖后，对单个积水酵母分支的分支特异性外切糖苷酶消化（β-D-半乳糖苷酶，N-乙酰基-β-D-氨基葡萄糖苷酶和α-D-甘露糖苷酶）进行适应化处理NeuAc的水解。为了进行分支特异性外切糖苷酶消化，分离获得的纯单唾液酸寡糖是必不可少的。然而，高效液相色谱法很难分离两种单唾液酸低聚糖，因为它们具有高度亲水性。因此，我们检查了具有疏水保护基（Fmoc和苄基）的化学保护。这些化学保护作用使我们能够通过合成规模的HPLC色谱柱（OD
• Improved isolation and characterization procedure of sialylglycopeptide from egg yolk powder
  作者：Lin Liu、Anthony R. Prudden、Gerlof P. Bosman、Geert-Jan Boons

  DOI：10.1016/j.carres.2017.10.001

  日期：2017.11

  that current isolation methods provide a glycopeptide contaminated with several related structures, one being a glycopeptide having a hexose directly attached to peptide backbone, most like through the hydroxyl containing side chain of the threonine moiety. Furthermore, current methods employ fresh egg yolks that need to be lyophilized and involve several tedious purification steps. Herein, we report

  唾液酸糖肽（SGP）是一种复杂的双天线N-聚糖，带有一个短肽片段，可以从鸡蛋的蛋黄中分离出来。这种天然产物作为半合成N-聚糖的起始原料而受到欢迎。我们已经发现，当前的分离方法提供了一种被几种相关结构污染的糖肽，一种是具有直接连接到肽主链上的己糖的糖肽，最像是通过苏氨酸部分的含羟基侧链。此外，当前的方法采用需要冻干的新鲜蛋黄，并且涉及几个繁琐的纯化步骤。本文中，我们报告了一种使用固/液萃取和HILIC-HPLC纯化从市售蛋黄粉中分离出克量均匀SGP的简便方法。
• Systematic Strategy for the Development of Glycosyltransferase Inhibitors: Diversity-Oriented Synthesis of FUT8 Inhibitors
  作者：Yoshiyuki Manabe、Koichi Fukase、Koki Hizume、Yohei Takakura、Shinji Takamatsu、Eiji Miyoshi、Yoshihiro Kamada、Ramón Hurtado-Guerrero

  DOI：10.1055/a-2221-9096

  日期：——

  we investigated the development of FUT8 inhibitors with structural elements encompassing both the glycosyl donor (GDP-fucose) and acceptor (N-glycan) of FUT8. To efficiently optimize the structure of FUT8 inhibitors, we employed a strategy involving fragmentation of the target structure, followed by a structure optimization using a diversity-oriented synthesis approach. This study proposes an efficient

  聚糖根据其结构控制各种生物过程。特别是，由 α1,6-岩藻糖基转移酶 (FUT8) 形成的核心岩藻糖对多种生物过程具有重大影响。在这项研究中，我们研究了 FUT8 抑制剂的开发，其结构元件包含 FUT8 的糖基供体（GDP-岩藻糖）和受体（N-聚糖）。为了有效优化 FUT8 抑制剂的结构，我们采用了一种策略，包括目标结构的片段化，然后使用面向多样性的合成方法进行结构优化。这项研究提出了一种加速中间分子结构优化的有效策略。
• Building blocks for glycoproteins: Synthesis of the ribonuclease B fragment 21–25 containing an undecasaccharide N-glycan
  作者：Carlo Unverzagt

  DOI：10.1016/s0040-4039(97)01278-1

  日期：1997.8

  A glycosylated fragment of the bovine glycoprotein ribonuclease B (1) was synthesized corresponding to amino acids 21-25 with a complex type biantennary N-glycan linked to Asn(24). The total synthesis of the undecasaccharide-glycopentapeptide 1 was accomplished by modem solution phase glycopeptide chemistry combined with enzymatic techniques for the removal of protective groups and a regio- and stereoselective transfer of the terminal carbohydrates using glycosyltransferases. (C) 1997 Elsevier Science Ltd.