phenyl O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->3)-O-(6-deoxy-β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->3)-O-(6-deoxy-β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside
• 英文别名: GlcNAc(b1-3)D-Fuc(b1-4)Glc(b)-O-Ph；N-[(2S,3R,4R,5S,6R)-2-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-phenoxyoxan-3-yl]oxy-3,5-dihydroxy-6-methyloxan-4-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• 化学式: C₂₆H₃₉NO₁₅
• 分子量: 605.593
• InChiKey: BLYWAQIGVUDSLV-KUIXVJNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  42
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  246
• 氢给体数：
  9
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 在 palladium on activated charcoal 苯磺酰胺 、 N-溴代丁二酰亚胺(NBS) 、 4 A molecular sieve 、 Neisseria meningitidis N-acetylglucosaminyl transferase 、 三氟化硼乙醚 、 氢气 、 sodium methylate 、 对甲苯磺酸 、 barium carbonate 作用下， 以 吡啶 、 甲醇 、 四氯化碳 、 二氯甲烷 、 乙酸乙酯 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0~85.0 ℃ 、20.0 kPa 条件下， 反应 60.5h， 生成 phenyl O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->3)-O-(6-deoxy-β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of deoxy and acylamino derivatives of lactose and use of these for probing the active site of Neisseria meningitidis N-acetylglucosaminyltransferase

  摘要：

  Derivatives of lactose with the galactose ring substituents replaced by deoxy or acylamino functions were prepared. The 2'-, 3'-. 4'- and 6'-deoxy, 3'-acetamido and 3'-benzamido derivatives of phenyl 4-O-(beta-D-galactopyranosyl)-beta-D-glucopyranoside (phenyl P-lactoside) were synthesized from disaccharide or monosaccharide precursors. The derivatives were tested as substrates for the N-acetylglucosaminyltransferase from Neisseria meningitidis, which uses lactosyl derivatives as acceptors and UDP-GlcNAc as the donor in a beta-(1-->3) glycosylation reaction. The 6'-deoxy derivative was nearly threefold as active as phenyl beta-lactoside, whereas the 2'- and 4'-deoxy derivatives were less active. The other derivatives were inactive, as expected. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.11.017

文献信息

• Synthesis of deoxy and acylamino derivatives of lactose and use of these for probing the active site of Neisseria meningitidis N-acetylglucosaminyltransferase
  作者：Ulrika Westerlind、Per Hagback、Björn Tidbäck、Lotta Wiik、Ola Blixt、Nahid Razi、Thomas Norberg

  DOI：10.1016/j.carres.2004.11.017

  日期：2005.2

  Derivatives of lactose with the galactose ring substituents replaced by deoxy or acylamino functions were prepared. The 2'-, 3'-. 4'- and 6'-deoxy, 3'-acetamido and 3'-benzamido derivatives of phenyl 4-O-(beta-D-galactopyranosyl)-beta-D-glucopyranoside (phenyl P-lactoside) were synthesized from disaccharide or monosaccharide precursors. The derivatives were tested as substrates for the N-acetylglucosaminyltransferase from Neisseria meningitidis, which uses lactosyl derivatives as acceptors and UDP-GlcNAc as the donor in a beta-(1-->3) glycosylation reaction. The 6'-deoxy derivative was nearly threefold as active as phenyl beta-lactoside, whereas the 2'- and 4'-deoxy derivatives were less active. The other derivatives were inactive, as expected. (C) 2004 Elsevier Ltd. All rights reserved.