2-乙酰氨基-6-O-(2-乙酰氨基-2-脱氧-B-D-D-吡喃葡萄糖基)-3-O-(B-D吡喃半乳糖基)-2-脱氧-A-D吡喃半乳糖 | 149793-99-7

• 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-6-O-(2-乙酰氨基-2-脱氧-B-D-D-吡喃葡萄糖基)-3-O-(B-D吡喃半乳糖基)-2-脱氧-A-D吡喃半乳糖
• 英文名称: N-[(2S,3R,4R,5R,6R)-6-((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-2,5-dihydroxy-4-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide
• 英文别名: beta-D-Galp-(1->3)-[beta-D-GlcpNAc-(1->6)]-alpha-D-GalpNAc；N-[(2R,3R,4R,5S,6R)-2-[[(2R,3R,4R,5R,6S)-5-acetamido-3,6-dihydroxy-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 149793-99-7
• 化学式: C₂₂H₃₈N₂O₁₆
• 分子量: 586.548
• InChiKey: AULDNGHDBFNGGC-XYVIJKTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.3
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  286
• 氢给体数：
  11
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  半乳-N-二糖 、 在 sodium hydroxide 、 乙二胺四乙酸 、 DL-dithiothreitol 、 苯甲基磺酰氟 、 亮抑酶肽半硫酸盐单水合物 、 phosphoenolpyruvate trisodium salt 、 胃酶抑素 A 、 尿苷-5’-二磷酸 、 magnesium chloride 、 Tween 20 、 4-羟乙基哌嗪乙磺酸 作用下， 生成 N-[(2R,3R,4R,5R,6R)-6-((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-2,5-dihydroxy-4-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide 、 2-乙酰氨基-6-O-(2-乙酰氨基-2-脱氧-B-D-D-吡喃葡萄糖基)-3-O-(B-D吡喃半乳糖基)-2-脱氧-A-D吡喃半乳糖
  参考文献：
  名称：

  A combined chemical and enzymatic strategy for the construction of carbohydrate-containing antigen core units

  摘要：

  Glycosidase-mediated coupling of glycal acceptors with galactose donors affords beta1,3-linked disaccharides that are versatile intermediates for further chemical and enzymatic manipulation. The utility of these disaccharides is demonstrated by the elaboration of these compounds into the type I and type IV core disaccharides of carbohydrate-containing antigens. Further conversion of the type IV disaccharide to a mucin-type trisaccharide (Galbeta1,3(GlcNAcbeta1,6)GalNAc) was accomplished with the use of a beta1,6-N-acetylglucosaminyltransferase. This combined use of enzymatic and chemical methodologies allows for the rapid assembly, with high regio- and stereoselectivity, of core oligosaccharides of biologically important glycoconjugates.

  DOI：

  10.1021/jo00068a030

文献信息

• A combined chemical and enzymatic strategy for the construction of carbohydrate-containing antigen core units
  作者：Gary C. Look、Yoshitaka Ichikawa、Gwo Jenn Shen、Pi Wan Cheng、Chi Huey Wong

  DOI：10.1021/jo00068a030

  日期：1993.7

  Glycosidase-mediated coupling of glycal acceptors with galactose donors affords beta1,3-linked disaccharides that are versatile intermediates for further chemical and enzymatic manipulation. The utility of these disaccharides is demonstrated by the elaboration of these compounds into the type I and type IV core disaccharides of carbohydrate-containing antigens. Further conversion of the type IV disaccharide to a mucin-type trisaccharide (Galbeta1,3(GlcNAcbeta1,6)GalNAc) was accomplished with the use of a beta1,6-N-acetylglucosaminyltransferase. This combined use of enzymatic and chemical methodologies allows for the rapid assembly, with high regio- and stereoselectivity, of core oligosaccharides of biologically important glycoconjugates.