2-乙酰氨基-2-脱氧-4-o-([4-o-beta-d-氟代半乳糖]-beta-d-氟代半乳糖)-d-吡喃葡萄糖 | 115114-32-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-乙酰氨基-2-脱氧-4-o-([4-o-beta-d-氟代半乳糖]-beta-d-氟代半乳糖)-d-吡喃葡萄糖
• 中文别名: 2-乙酰氨基-2-脱氧-4-O-[(4-O-Β-D-吡喃半乳糖)-Β-D-吡喃半乳糖基]-D-吡喃葡萄糖
• 英文名称: 2-Acetamido-2-deoxy-4-O-(4-O-Beta-D-galactopyranosyl-beta-D-galactopyranosyl)-D-glucopyranose
• 英文别名: β-D-Gal-(1->4)-β-D-Gal-(1->4)-D-GlcNac；betaLacNAc；N-[(3R,4R,5S,6R)-5-[(2S,3R,4R,5R,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2,4-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 115114-32-4
• 化学式: C₂₀H₃₅NO₁₆
• mdl: MFCD00058661
• 分子量: 545.495
• InChiKey: QOITYCLKNIWNMP-QDRCFXCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.9
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  278
• 氢给体数：
  11
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  2-naphthylamino-6,8-disulfonic acid monopotassium salt 、 2-乙酰氨基-2-脱氧-4-o-([4-o-beta-d-氟代半乳糖]-beta-d-氟代半乳糖)-d-吡喃葡萄糖 在 sodium hydroxide 、 sodium cyanoborohydride 作用下， 生成
  参考文献：
  名称：

  A new method for sequencing linear oligosaccharides on gels using charged, fluorescent conjugates

  摘要：

  A new method is described for sequencing linear oligosaccharides on gels using charged, fluorescent conjugates. The reducing ends of various mono-, di-, tri-, and tetra-saccharides were conjugated with monopotassium 7-amino-1,3-naphthalenedisulfonate (a fluorescent and negatively charged compound) by reductive amination using sodium cyanoborohydride. The sugar conjugates were purified by preparative gradient polyacrylamide gel electrophoresis followed by a newly developed technique involving their semi-dry transfer to positively charged nylon membranes and elution with sodium chloride. The structures of a monosaccharide- and trisaccharide-conjugate were established by f.a.b.-m.s. and 2D n.m.r. Seven linear oligosaccharide-fluorescent conjugates were treated sequentially with exoglycosidases and with endoglycosidases. Analysis of the products by gel electrophoresis provided sequence information. These methods may be useful for sequencing oligosaccharides that are chemically or enzymically (endoglycosidase) released from glycoproteins, glycolipids, and proteoglycans.

  DOI：

  10.1016/s0008-6215(00)90538-x
• 作为产物：
  描述：

  N-acetyl-D-lactosamine 、 alkaline earth salt of/the/ methylsulfuric acid 在 β-galactanase 、 sodium acetate 作用下， 以 水 为溶剂， 反应 48.0h， 以15.5%的产率得到2-乙酰氨基-2-脱氧-4-o-([4-o-beta-d-氟代半乳糖]-beta-d-氟代半乳糖)-d-吡喃葡萄糖
  参考文献：
  名称：

  使用柠檬青霉菌中的β-半乳糖酶在非还原端酶促合成含Galβ-> 4Gal二糖的寡糖。

  摘要：

  用来自柠檬青霉的β-半乳糖苷酶进行转糖基化反应。使用大豆阿拉伯半乳聚糖作为供体和含有β-半乳糖基残基的单糖或二糖衍生物作为受体，研究了转糖基化反应中的区域选择性。我们还合成了含有Gal beta 1-> 4Gal序列的寡糖，例如Gal beta 1-> 4Gal beta1-> 4Glc，Gal beta 1-> 4Gal beta 1-> 3GlcNac，Gal beta 1-> 4Gal beta 1-> 4GlcNAc，Gal beta 1-> 4Gal beta 1-> 6GlcNAc和Gal beta 1-> 4Gal beta 1-> 3GalNAc，用于复杂糖链的全合成。

  DOI：

  10.1271/bbb.61.1258

文献信息

• US5725804A
  申请人：——

  公开号：US5725804A

  公开（公告）日：1998-03-10
• A new method for sequencing linear oligosaccharides on gels using charged, fluorescent conjugates
  作者：Kyung-Bok. Lee、Ali Al-Hakim、Duraikkannu Loganathan、Robert J. Linhardt

  DOI：10.1016/s0008-6215(00)90538-x

  日期：1991.8

  A new method is described for sequencing linear oligosaccharides on gels using charged, fluorescent conjugates. The reducing ends of various mono-, di-, tri-, and tetra-saccharides were conjugated with monopotassium 7-amino-1,3-naphthalenedisulfonate (a fluorescent and negatively charged compound) by reductive amination using sodium cyanoborohydride. The sugar conjugates were purified by preparative gradient polyacrylamide gel electrophoresis followed by a newly developed technique involving their semi-dry transfer to positively charged nylon membranes and elution with sodium chloride. The structures of a monosaccharide- and trisaccharide-conjugate were established by f.a.b.-m.s. and 2D n.m.r. Seven linear oligosaccharide-fluorescent conjugates were treated sequentially with exoglycosidases and with endoglycosidases. Analysis of the products by gel electrophoresis provided sequence information. These methods may be useful for sequencing oligosaccharides that are chemically or enzymically (endoglycosidase) released from glycoproteins, glycolipids, and proteoglycans.
• Enzymatic Synthesis of Oligosaccharides Containing Gal<i>β</i>→4Gal Disaccharide at the Non-Reducing End Using<i>β</i>-Galactanase from<i>Penicillium citrinum</i>
  作者：Hiroshi Fujimoto、Hirofumi Nakano、Megumi Isomura、Sumio Kitahata、Katsumi Ajisaka

  DOI：10.1271/bbb.61.1258

  日期：1997.1

  The transglycosylation reaction was done with a beta-galactanase from Penicillium citrinum. The regioselectivity in the transglycosylation reaction was studied using soy bean arabinogalactan as a donor and mono- or disaccharide derivatives containing beta-galactosyl residue as acceptors. We also synthesized oligosaccharides containing Gal beta 1-->4Gal sequence such as Gal beta 1-->4Gal beta1-->4Glc

  用来自柠檬青霉的β-半乳糖苷酶进行转糖基化反应。使用大豆阿拉伯半乳聚糖作为供体和含有β-半乳糖基残基的单糖或二糖衍生物作为受体，研究了转糖基化反应中的区域选择性。我们还合成了含有Gal beta 1-> 4Gal序列的寡糖，例如Gal beta 1-> 4Gal beta1-> 4Glc，Gal beta 1-> 4Gal beta 1-> 3GlcNac，Gal beta 1-> 4Gal beta 1-> 4GlcNAc，Gal beta 1-> 4Gal beta 1-> 6GlcNAc和Gal beta 1-> 4Gal beta 1-> 3GalNAc，用于复杂糖链的全合成。