3-sulfo-β-D-galactopyranosyl-(1->3)-[(α-L-fucopyranosyl)-(1->4)]-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->3)-β-D-galactopyranosyl-(1->4)-D-glucopyranose sodium salt

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-sulfo-β-D-galactopyranosyl-(1->3)-[(α-L-fucopyranosyl)-(1->4)]-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->3)-β-D-galactopyranosyl-(1->4)-D-glucopyranose sodium salt
• 英文别名: sodium;N-[(2S,3R,4R,5S,6R)-4-[(2R,3R,4S,5S,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-sulfooxyoxan-2-yl]oxy-2-[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-4-yl]oxy-6-(hydroxymethyl)-5-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]ethanimidate
• 化学式: C₃₂H₅₄NO₂₈S*Na
• 分子量: 955.826
• InChiKey: AQGFAHGSVOBGLN-OFPHSQGJSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -14.28
• 重原子数：
  63
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  474
• 氢给体数：
  15
• 氢受体数：
  29

反应信息

• 作为产物：
  描述：

  O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-4,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate 、 5`-二磷酸鸟嘌呤核苷-岩藻糖二钠盐 、 β-D-galactopyranosyl-(1->4)-1-thio-β-D-glucopyranoside 生成 3-sulfo-β-D-galactopyranosyl-(1->3)-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->3)-β-D-galactopyranosyl-(1->4)-D-glucopyranose sodium salt 、 3-sulfo-β-D-galactopyranosyl-(1->3)-[(α-L-fucopyranosyl)-(1->4)]-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->3)-β-D-galactopyranosyl-(1->4)-D-glucopyranose sodium salt 、 lacto-N-tetraose 、 Acetylglucosamine
  参考文献：
  名称：

  Chemo-enzymatic supported synthesis of the 3-sulfated Lewisa pentasaccharide on a multimeric polyethylene glycol

  摘要：

  The 3-sulfated Lewis(a) pentasaccharide was synthesized on multimeric-based polyethylene glycol support. Coupling of O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-(1 -> 3)-4,6-di-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl trichloroacetimidate with (2,6-di-O-acetyl-beta-D-galactopyranosyl)-(1 -> 4)-(2,3,6-tri-O-acetyl-beta-D-glucopyranoside) bound onto the polymer afforded lacto-N-tetraose, which was then regioselectively sulfated at the 3-OH position of the terminal galactose using the stannylene procedure. Fucosylation of the sulfated tetrasaccharide was performed using an immobilized fucosyltransferase FucTIII to give the title compound after cleavage. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.01.005

文献信息

• Chemo-enzymatic supported synthesis of the 3-sulfated Lewisa pentasaccharide on a multimeric polyethylene glycol
  作者：Annie Malleron、Christine Le Narvor

  DOI：10.1016/j.carres.2008.01.005

  日期：2008.4

  The 3-sulfated Lewis(a) pentasaccharide was synthesized on multimeric-based polyethylene glycol support. Coupling of O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-(1 -> 3)-4,6-di-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl trichloroacetimidate with (2,6-di-O-acetyl-beta-D-galactopyranosyl)-(1 -> 4)-(2,3,6-tri-O-acetyl-beta-D-glucopyranoside) bound onto the polymer afforded lacto-N-tetraose, which was then regioselectively sulfated at the 3-OH position of the terminal galactose using the stannylene procedure. Fucosylation of the sulfated tetrasaccharide was performed using an immobilized fucosyltransferase FucTIII to give the title compound after cleavage. (C) 2008 Elsevier Ltd. All rights reserved.