methyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->2)-α-D-mannopyranosyl-(1->3)-[2-acetamido-2-deoxy-β-D-glucopyanosyl-(1->2)-α-D-mannopyranosyl-(1->6)]-α-D-mannopyranoside | 68628-51-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->2)-α-D-mannopyranosyl-(1->3)-[2-acetamido-2-deoxy-β-D-glucopyanosyl-(1->2)-α-D-mannopyranosyl-(1->6)]-α-D-mannopyranoside
• 英文别名: methyl 3,6-di-O-<2-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-α-D-mannopyranosyl>-α-D-mannopyranoside；methyl 3,6-di-O-(2-deoxy-2-acetamide-β-D-glucopyranosyl-2-O-α-D-mannopyranosyl)-α-D-mannopyranoside；GlcNAc(b1-2)Man(a1-3)[GlcNAc(b1-2)Man(a1-6)]a-Man1Me；N-[(2S,3R,4R,5S,6R)-2-[(2S,3S,4S,5S,6R)-2-[[(2R,3R,4S,5S,6S)-4-[(2R,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-3,5-dihydroxy-6-methoxyoxan-2-yl]methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 68628-51-3
• 化学式: C₃₅H₆₀N₂O₂₆
• 分子量: 924.859
• InChiKey: VRIBKPUEENOKSF-RXSBVVMGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -9
• 重原子数：
  63
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  434
• 氢给体数：
  16
• 氢受体数：
  26

反应信息

• 作为反应物：
  描述：

  methyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->2)-α-D-mannopyranosyl-(1->3)-[2-acetamido-2-deoxy-β-D-glucopyanosyl-(1->2)-α-D-mannopyranosyl-(1->6)]-α-D-mannopyranoside 、 UDP-Gal 在 苯磺酰胺 、 β-1,4-galactosyltransferase 、 7 U alkaline phosphatase 作用下， 以 various solvent(s) 为溶剂， 反应 120.0h， 以69%的产率得到Gal(b1-4)GlcNAc(b1-2)Man(a1-3)[Gal(b1-4)GlcNAc(b1-2)Man(a1-6)]a-Man1Me
  参考文献：
  名称：

  使用α-1,3-岩藻糖基转移酶V化学合成L-半乳糖基化的二聚唾液酸化Lewis X结构。

  摘要：

  L-半乳糖基化的二聚唾液酸路易斯X（SLeX）已采用化学和酶促合成方法的组合制备。GDP-L-半乳糖已化学合成。使用人alpha-1,3-岩藻糖基转移酶V将L-半乳糖酶转移到受体（Sia-alpha2,3-Gal-beta1,4-GlcNAc-beta1,3 / 6）2-Man-alpha1-OMe上。

  DOI：

  10.1016/s0968-0896(00)00187-5
• 作为产物：
  描述：

  methyl 3,6-di-O-<2-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl>-2,4-di-O-benzyl-α-D-mannopyranoside 在 20% palladium hydroxide-activated charcoal 、 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 25.0h， 以11 mg的产率得到methyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->2)-α-D-mannopyranosyl-(1->3)-[2-acetamido-2-deoxy-β-D-glucopyanosyl-(1->2)-α-D-mannopyranosyl-(1->6)]-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of N -glycan units for assessment of substrate structural requirements of N -acetylglucosaminyltransferase III

  摘要：

  N-Acetylglucosaminyltransferase (GnT) III is a glycosyltransferase which produces bisected N-glycans by transferring GlcNAc to the 4-position of core mannose. Bisected N-glycans are involved in physiological and pathological processes through the functional regulation of their carrier proteins. An understanding of the biological functions of bisected glycans will be greatly accelerated by use of specific inhibitors of GnT-III. Thus far, however, such inhibitors have not been developed and even the substrate-binding mode of GnT-III is not fully understood. To gain insight into structural features required of the substrate, we systematically synthesized four N-glycan units, the branching parts of the bisected and non-bisected N-glycans. The series of syntheses were achieved from a common core trimannose, giving bisected tetra-and hexasaccharides as well as non-bisected tri- and pentasaccharides. A competitive GnT-III inhibition assay using the synthetic substrates revealed a vital role for the Man beta(1-4) GlcNAc moiety. In keeping with previous reports, GlcNAc at the alpha 1,3-branch is also involved in the interaction. The structural requirements of GnT-III elucidated in this study will provide a basis for rational inhibitor design. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.07.074

文献信息

• Synthetic studies on cell surface glycans 3
  作者：Tomoya Ogawa、Kiyoaki Katano、Kikuo Sasajima、Masanao Matsui

  DOI：10.1016/s0040-4020(01)92345-2

  日期：1981.1