α-Man-(1<*>6)<*> α-Man-(1<*>3)<*> β-Man-(1<*>4)-β-GlcNAc-(1<*>4)-β-GlcNAc<*>Asn | 67739-90-6

• 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: α-Man-(1<*>6)<*> α-Man-(1<*>3)<*> β-Man-(1<*>4)-β-GlcNAc-(1<*>4)-β-GlcNAc<*>Asn
• 英文别名: N-{O-(α-D-mannopyranosyl)-(1->6)-O-[(α-D-mannopyranosyl)-(1->3)]-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；TriMan；(2S)-4-[[(2R,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(2S,3S,4S,5R,6R)-3,5-dihydroxy-4-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]amino]-2-amino-4-oxobutanoic acid
• CAS: 67739-90-6
• 化学式: C₃₈H₆₄N₄O₂₈
• 分子量: 1024.94
• InChiKey: UQEBOUGFBLKBSF-MFKWYPGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -13.7
• 重原子数：
  70
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  517
• 氢给体数：
  19
• 氢受体数：
  29

反应信息

• 作为产物：
  描述：

  在 钯 氢气 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 16.0h， 生成 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：

  Synthesis of an Asparagine-Linked Core Pentasaccharide by Means of Simultaneous Inversion Reactions

  摘要：

  DOI：

  10.1080/07328309908544039

文献信息

• 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
• A Lectin from Platypodium elegans with Unusual Specificity and Affinity for Asymmetric Complex N-Glycans
  作者：Raquel Guimarães Benevides、Géraldine Ganne、Rafael da Conceição Simões、Volker Schubert、Mathäus Niemietz、Carlo Unverzagt、Valérie Chazalet、Christelle Breton、Annabelle Varrot、Benildo Sousa Cavada、Anne Imberty

  DOI：10.1074/jbc.m112.375816

  日期：2012.7

  complexed with branched trimannose and symmetrical complex-type Asn-linked heptasaccharide have been solved at 2.1 and 1.65 A resolution, respectively. The lectin adopts the canonical dimeric organization of legume lectins. The trimannose bridges the binding sites of two neighboring dimers, resulting in the formation of infinite chains in the crystal. The Asn-linked heptasaccharide binds with the 6-arm

  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
• A Versatile Urea Type Linker for Functionalizing Natural Glycans and Its Validation in Glycan Arrays
  作者：Sonia Serna、Raik Artschwager、Damián Pérez‐Martínez、Rosa Lopez、Niels‐Christian Reichardt

  DOI：10.1002/chem.202301494

  日期：2023.9.15

  The isolation from organisms and readily available glycoproteins has become an increasingly convenient source of N‐glycans for multiple applications including glycan microarrays, as reference standards in glycan analysis or as reagents that improve bioavailability of protein and peptide therapeutics through conjugation. A problematic step in the isolation process on a preparative scale can be the attachment of a linker for the improved purification, separation, immobilization and quantification of the glycan structures. Addressing this issue, we firstly aimed for the development of an UV active linker for a fast and reliable attachment to anomeric glycosylamines via urea bond formation. Secondly, we validated the new linker on glycan arrays in a comparative study with a collection of N‐glycans which were screened against various lectins. In total, we coupled four structurally varied N‐glycans to four different linkers, immobilized all constructs on a microarray and compared their binding affinities to four plant and fungal lectins of widely described specificity. Our study shows that the urea type linker showed an overall superior performance for lectin binding and once more, highlights the often neglected influence of the choice of linker on lectin recognition.

  摘要从生物体和现成的糖蛋白中分离 N-聚糖已成为越来越方便的 N-聚糖来源，可用于多种应用，包括聚糖微阵列、聚糖分析参考标准或通过共轭提高蛋白质和肽疗法生物利用度的试剂。在制备规模的分离过程中，一个棘手的步骤可能是添加连接剂，以改进聚糖结构的纯化、分离、固定和定量。针对这一问题，我们首先致力于开发一种紫外线活性连接剂，通过脲键的形成快速可靠地连接到异构糖胺上。其次，我们通过与针对各种凝集素进行筛选的一系列 N-聚糖进行比较研究，在聚糖阵列上验证了这种新型连接剂。我们总共将四种结构不同的 N-聚糖与四种不同的连接体进行了连接，将所有构建体固定在微阵列上，并比较了它们与四种植物和真菌凝集素的结合亲和力，这些凝集素具有广泛的特异性。我们的研究表明，尿素型连接体与凝集素结合的整体性能更优越，这再次凸显了连接体的选择对凝集素识别的影响往往被忽视。
• Synthesis of an Asparagine-Linked Core Pentasaccharide by Means of Simultaneous Inversion Reactions
  作者：Ichiro Matsuo、Megumi Isomura、Katsumi Ajisaka

  DOI：10.1080/07328309908544039

  日期：1999.1.1