propyl 2,6-bis-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-α-D-mannopyranoside | 150492-44-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: propyl 2,6-bis-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-α-D-mannopyranoside
• 英文别名: GlcNAc(b1-2)[GlcNAc(b1-6)]Man(a)-O-Pr；N-[(2R,3R,4R,5S,6R)-2-[[(2R,3S,4S,5S,6S)-5-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydroxy-6-propoxyoxan-2-yl]methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 150492-44-7
• 化学式: C₂₅H₄₄N₂O₁₆
• 分子量: 628.628
• InChiKey: BKGTWLSLPINCQS-YVOJAWQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.9
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  275
• 氢给体数：
  10
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  uridine 5'-(6-deoxy-α-D-galactopyranosyl) diphosphate diammonium salt 、 propyl 2,6-bis-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-α-D-mannopyranoside 在 N-2-hydroxyethylpiperazine-N,-2-ethanesulfonic acid buffer 、 manganese(ll) chloride 作用下， 反应 48.0h， 以55%的产率得到D-Fuc(b1-4)GlcNAc(b1-2)[D-Fuc(b1-4)GlcNAc(b1-6)]Man(a)-O-Pr
  参考文献：
  名称：

  Enzymic transfer of 6-modified d-galactosyl residues: synthesis of biantennary penta- and hepta-saccharides having two 6-deoxy-d-galactose residues at the nonreducing end and evaluation of 6-deoxy-d-galactosyl transfer to glycoprotein using bovine β-(1 → 4)-galactosyltransferase and UDP-6-deoxy-d-galactose

  摘要：

  UDP-6-Deoxy-D-galactose and UDP-6-deoxy-6-fluoro-D-galactose were synthesized and their transfer to 2-acetamido-2-deoxy-D-glucose (N-acetyl-D-glucosamine) by beta-(1 --> 4)galactosyltransferase was examined. The transfer rates of 6-deoxy-D-galactose and 6-deoxy-6-fluoro-D-galactose were 1.3 and 0.2% of that of D-galactosyl transfer, respectively. The 2-acetamido-4-O-(6-deoxy-beta-D-galactopyranosyl)-2-deoxy-D-glucopyranose (6'-deoxy-N-acetyllactosamine) and methyl 2-acetamido-4-O-(6-deoxy-6-fluoro-beta-D-galactopyranosyl)-2-deoxy-D-glucopyranoside (6'-deoxy-6'-fluoro-N-acetyllactosamine) were synthesized enzymatically in 30 and 59% yields, respectively. Further, 6-deoxy-D-galactose could be completely transferred to N-linked type biantennary oligosaccharides having two N-acetyl-D-glucosaminyl residues at the nonreducing end to give the corresponding penta- and hepta-saccharides in 55 and 57% yields, respectively. An assay of 6-deoxy-D-galactosyl transfer using asialo agalacto alpha(1)-acid glycoprotein as an acceptor suggested that 6-deoxy-D-galactose was transferred to about 30% of the N-acetyl-D-glucosaminyl residues in the N-linked oligosaccharides of the glycoprotein.

  DOI：

  10.1016/0008-6215(94)00369-q
• 作为产物：
  描述：

  乙基3,4,6-三-O-乙酰基-2-脱氧-2-邻苯二甲酰亚胺基-1-硫代-β-D-吡喃葡萄糖苷 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 4 A molecular sieve 、 氢气 、 sodium methylate 、 一水合肼 、 溶剂黄146 、 三氟甲烷磺酸甲酯 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 66.5h， 生成 propyl 2,6-bis-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-α-D-mannopyranoside
  参考文献：
  名称：

  Enzymic transfer of 6-modified d-galactosyl residues: synthesis of biantennary penta- and hepta-saccharides having two 6-deoxy-d-galactose residues at the nonreducing end and evaluation of 6-deoxy-d-galactosyl transfer to glycoprotein using bovine β-(1 → 4)-galactosyltransferase and UDP-6-deoxy-d-galactose

  摘要：

  UDP-6-Deoxy-D-galactose and UDP-6-deoxy-6-fluoro-D-galactose were synthesized and their transfer to 2-acetamido-2-deoxy-D-glucose (N-acetyl-D-glucosamine) by beta-(1 --> 4)galactosyltransferase was examined. The transfer rates of 6-deoxy-D-galactose and 6-deoxy-6-fluoro-D-galactose were 1.3 and 0.2% of that of D-galactosyl transfer, respectively. The 2-acetamido-4-O-(6-deoxy-beta-D-galactopyranosyl)-2-deoxy-D-glucopyranose (6'-deoxy-N-acetyllactosamine) and methyl 2-acetamido-4-O-(6-deoxy-6-fluoro-beta-D-galactopyranosyl)-2-deoxy-D-glucopyranoside (6'-deoxy-6'-fluoro-N-acetyllactosamine) were synthesized enzymatically in 30 and 59% yields, respectively. Further, 6-deoxy-D-galactose could be completely transferred to N-linked type biantennary oligosaccharides having two N-acetyl-D-glucosaminyl residues at the nonreducing end to give the corresponding penta- and hepta-saccharides in 55 and 57% yields, respectively. An assay of 6-deoxy-D-galactosyl transfer using asialo agalacto alpha(1)-acid glycoprotein as an acceptor suggested that 6-deoxy-D-galactose was transferred to about 30% of the N-acetyl-D-glucosaminyl residues in the N-linked oligosaccharides of the glycoprotein.

  DOI：

  10.1016/0008-6215(94)00369-q