ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-2-O-levulinoyl-1-thio-β-D-glucopyranoside | 904689-98-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-2-O-levulinoyl-1-thio-β-D-glucopyranoside
• 英文别名: ethyl 2-Oacetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1-3)-4,6-O-benzylidene-2-levulinoyl-1-thio-β-D-glucopyranoside
• CAS: 904689-98-1
• 化学式: C₄₉H₅₆O₁₃S
• 分子量: 885.042
• InChiKey: OQGZCKWIWBXUMW-FSXQYDAXSA-N

物化性质

• 沸点：
  911.2±65.0 °C(predicted)
• 密度：
  1.29±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.29
• 重原子数：
  63.0
• 可旋转键数：
  20.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  143.51
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-2-O-levulinoyl-1-thio-β-D-glucopyranoside 、 三氟甲磺酸酐 在 2,6-二叔丁基-4-甲基吡啶 、 二苯基亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 1.17h， 生成
  参考文献：
  名称：

  ‘Naked’ and Hydrated Conformers of the Conserved Core Pentasaccharide of N-linked Glycoproteins and Its Building Blocks

  摘要：

  N-glycosylation of eukaryotic proteins is widespread and vital to survival. The pentasaccharide unit -Man(3)GlcNAc(2)- lies at the protein-junction core of all oligosaccharides attached to asparagine side chains during this process. Although its absolute conservation implies an indispensable role, associated perhaps with its structure, its unbiased conformation and the potential modulating role of solvation are unknown; both have now been explored through a combination of synthesis, laser spectroscopy, and computation. The proximal -GlcNAc-GlcNAc- unit acts as a rigid rod, while the central, and unusual, -Man-beta-1,4-GlcNAc- linkage is more flexible and is modulated by the distal Man-alpha-1,3- and Man-alpha-1,6- branching units. Solvation stiffens the 'rod' but leaves the distal residues flexible, through a beta-Man pivot, ensuring anchored projection from the protein shell while allowing flexible interaction of the distal portion of N-glycosylation with bulk water and biomolecular assemblies.

  DOI：

  10.1021/ja4056678
• 作为产物：
  描述：

  ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside 在 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 39.5h， 生成 ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-2-O-levulinoyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  N-聚糖恶唑啉的合成：内己糖胺酶的供体催化糖基化。

  摘要：

  恶唑啉单，二，三和六糖，对应于N-连接的糖蛋白高甘露糖聚糖的核心成分，被合成为潜在的糖基供体，用于内己糖胺酶催化糖肽的糖基化和糖蛋白重塑。关键的β-D-Manp-（1-> 4）-D-GlcpNAc连接是通过顺序三氟甲磺酸酯化和亲核取代作用通过葡萄糖二糖底物的差向异构化合成的。恶唑啉直接由端基OPMP保护的N-乙酰基氨基葡萄糖衍生物形成。用三糖恶唑啉供体证明了合成的β-D-GlcpNAcAsn糖基氨基酸的高效内己糖胺酶催化糖基化。

  DOI：

  10.1016/j.carres.2006.03.007

文献信息

• An Endoglycosidase with Alternative Glycan Specificity Allows Broadened Glycoprotein Remodelling
  作者：Jonathan J. Goodfellow、Kavitha Baruah、Keisuke Yamamoto、Camille Bonomelli、Benjamin Krishna、David J. Harvey、Max Crispin、Christopher N. Scanlan、Benjamin G. Davis

  DOI：10.1021/ja301334b

  日期：2012.5.16

  Protein endoglycosidases are useful for biocatalytic alteration of glycans on protein surfaces, but the currently limited selectivity of endoglycosidases has prevented effective manipulation of certain N-linked glycans widely found in nature. Here we reveal that a bacterial endoglycosidase from Streptococcus pyogenes, EndoS, is complementary to other known endoglycosidases (EndoA, EndoH) used for current protein remodeling. It allows processing of complex-type N-linked glycans +/- core fucosylation but does not process oligomannose- or hybrid-type glycans. This biocatalytic activity now addresses previously refractory antibody glycoforms.