O-(6-deoxy-β-D-galactopyranosyl)-(1<*>4)-2-acetamido-2-deoxy-D-glucopyranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(6-deoxy-β-D-galactopyranosyl)-(1<*>4)-2-acetamido-2-deoxy-D-glucopyranose
• 英文别名: β-D-fucopyranosyl-(1->4)-2-acetamido-2-deoxy-D-glucopyranose；D-Fuc(b1-4)GlcNAc；N-[(3R,4R,5S,6R)-2,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]acetamide
• 化学式: C₁₄H₂₅NO₁₀
• 分子量: 367.353
• InChiKey: YSVYPLBRZMVZJE-WJNUYCRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  178
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-methyl-2-phosphonooxy-tetrahydro-pyran-3-yl ester 在 galactosyltransferase 、 HEPES buffer 、 alkaline phosphatase 作用下， 反应 48.0h， 生成 O-(6-deoxy-β-D-galactopyranosyl)-(1<*>4)-2-acetamido-2-deoxy-D-glucopyranose
  参考文献：
  名称：

  Synthesis of UDP-6-deoxy- and -6-fluoro-D-galactoses and their enzymatic glycosyl transfer to mono- and biantennary carbohydrate chains

  摘要：

  Glycosylation with chemicallY prepared UDP-6-deoxy-D-galactose and its 6-fluoro analog using bovine (1-4)-beta-D-galactosyltransferase was demonstrated to be effective enough for practical purpose. A biantennary pentasaccharide having two 6'-deoxylactosamine residues was synthesized.

  DOI：

  10.1016/0040-4039(93)85060-a

文献信息

• Formation of LacNAc mimetics employing novel donor substrates for enzymatic β1→4 galactosylation
  作者：Saskia Weingarten、Joachim Thiem

  DOI：10.1039/b400916a

  日期：——

  In examining C-6 modified 4-nitrophenyl β-D-galactopyranosides as donor structures the β-galactosidase (Bacillus circulans) revealed an unexpectedly broad substrate specificity which allowed successful syntheses of various disaccharide components.

  在研究作为供体结构的 C-6 修饰的 4-硝基苯基 δ-D-吡喃半乳糖苷时，δ-半乳糖苷酶（环状芽孢杆菌）显示出出人意料的广泛底物特异性，从而成功合成了各种双糖成分。
• 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
  作者：Yasuhiro Kajihara、Tsuyoshi Endo、Hiroyuki Ogasawara、Hisashi Kodama、Hironobu Hashimoto

  DOI：10.1016/0008-6215(94)00369-q

  日期：1995.4

  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.