ethyl β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside | 87019-37-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: ethyl 2-acetamido-2-deoxy-4-O-(β-D-galactopyranosyl)-β-D-glucopyranoside；ethyl 2-acetamido-2-deoxy-4-O-β-D-galactopyranosyl-β-D-glucopyranoside；ethyl β-N-acetyllactosaminide；Gal(b1-4)GlcNAc(b)-O-Et；N-[(2R,3R,4R,5S,6R)-2-ethoxy-4-hydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]acetamide
• CAS: 87019-37-2
• 化学式: C₁₆H₂₉NO₁₁
• 分子量: 411.406
• InChiKey: DIPBWOAXZNDTCN-NSSUFJHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.8
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  187
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2,2',3,3',4',6,6'-七-O-乙酰基-alpha-D-乳糖基溴化物 在 三氟甲磺酸三甲基硅酯 、 叠氮基三甲基硅烷 、 碘 、 sodium methylate 、 溶剂黄146 、 锌 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 55.0h， 生成 ethyl β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of multivalent N-acetyl lactosamine modified quantum dots for the study of carbohydrate and galectin-3 interactions

  摘要：

  Ternary core/shell CdSeS/ZnS-QDs coated with N-acetyl lactosamine was prepared as a fluorescent probe to study the interactions of N-acetyl lactosamine and galectin-3. The synthesis of N-acetyl lactosamine was achieved through the 'azidoiodoglycosylation' method. The amount of ligand coated on QDs was determined by H-1 NMR and ICP-OES. The interactions between carbohydrates and galectin-3 were measured using SPR. The results revealed that the affinity of galectin-3 with di- and multivalent N-acetyl lactosamine increased 20 and 184-fold, respectively. The prepared glyco-QDs could be used as an efficient fluorescent probe to study carbohydrates and galectin-3 interactions. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.035

文献信息

• Synthesis of Glyceroyl β-<i>N</i>-Acetyllactosaminide and Its Derivatives through a Condensation Reaction by Cellulase
  作者：Nozomu YASUTAKE、Kazuhide TOTANI、Yoichiro HARADA、Shinobu HARAGUCHI、Takeomi MURATA、Taichi USUI

  DOI：10.1271/bbb.67.1530

  日期：2003.1

  A condensation reaction between N-acetyllactosamine and glycerol was directly catalyzed by using a commercially available cellulase preparation from Trichoderma reesei. 1-O-β-N-Acetyllactosaminyl-(R, S)-glycerols (1) were readily synthesized in a 5% yield based on the N-acetyllactosamine added and conveniently isolated by two-step column chromatographies. The use of a partially purified enzyme increased 2.3-fold the yield of 1, compared to that of the crude enzyme containing β-D-galactosidase activity. When various alkanols (n:2-4) were used in the condensation reaction, the corresponding alkyl β-N-acetyllactosaminides were obtained in yields of 0.3-1.1% of the desired compounds.

  使用来自里氏木霉的市售纤维素酶制剂直接催化N-乙酰基乳糖胺和甘油之间的缩合反应。基于添加的 N-乙酰乳糖胺，可以轻松合成 1-O-β-N-乙酰基乳糖胺基-(R,S)-甘油 (1)，收率 5%，并通过两步柱色谱方便地分离。与含有 β-D-半乳糖苷酶活性的粗酶相比，使用部分纯化的酶可将 1 的产量提高 2.3 倍。当使用各种烷醇(n:2-4)进行缩合反应时​​，得到相应的烷基β-N-乙酰基乳糖胺，收率为0.3-1.1%。
• Wong, Ting C.; Lemieux, Raymond U., Canadian Journal of Chemistry, 1984, vol. 62, p. 1207 - 1213
  作者：Wong, Ting C.、Lemieux, Raymond U.

  DOI：——

  日期：——
• 2-Bromoethyl glycosides: applications in the synthesis of spacer-arm glycosides
  作者：Jan Dahmén、Torbjörn Frejd、Gunnar Grönberg、Thomas Lave、Göran Magnusson、Ghazi Noori

  DOI：10.1016/0008-6215(83)88059-8

  日期：1983.7
• Synthesis of multivalent N-acetyl lactosamine modified quantum dots for the study of carbohydrate and galectin-3 interactions
  作者：Yang Yang、Xiao-Chao Xue、Xiao-Feng Jin、Li-Jun Wang、Yin-Lin Sha、Zhong-Jun Li

  DOI：10.1016/j.tet.2012.06.035

  日期：2012.9

  Ternary core/shell CdSeS/ZnS-QDs coated with N-acetyl lactosamine was prepared as a fluorescent probe to study the interactions of N-acetyl lactosamine and galectin-3. The synthesis of N-acetyl lactosamine was achieved through the 'azidoiodoglycosylation' method. The amount of ligand coated on QDs was determined by H-1 NMR and ICP-OES. The interactions between carbohydrates and galectin-3 were measured using SPR. The results revealed that the affinity of galectin-3 with di- and multivalent N-acetyl lactosamine increased 20 and 184-fold, respectively. The prepared glyco-QDs could be used as an efficient fluorescent probe to study carbohydrates and galectin-3 interactions. (C) 2012 Elsevier Ltd. All rights reserved.