β-D-galactopyranosyl-(1->6)-2-acetamido-2-deoxy-α-D-glucopyranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-galactopyranosyl-(1->6)-2-acetamido-2-deoxy-α-D-glucopyranose
• 英文别名: Gal(b1-6)a-GlcNAc；N-[(2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-3-yl]acetamide
• 化学式: C₁₄H₂₅NO₁₁
• 分子量: 383.353
• InChiKey: ACKXCNXSQYSCQN-CXIHMHBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  198
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 在 palladium on activated charcoal 吡啶 、 sodium methylate 、 ammonium formate 、 四氯化锡 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 23.25h， 生成 β-D-galactopyranosyl-(1->6)-2-acetamido-2-deoxy-α-D-glucopyranose
  参考文献：
  名称：

  One-pot synthesis of β-d-Gal>(1 → 4)[β-d-Galp(1 → 6)]-d-GlcNAc, a ‘core’ trisaccharide linked O-glycosidically in glycoproteins of Trypanosoma cruzi

  摘要：

  Tin(IV) chloride-promoted condensation of benzyl 2-acetamido-3-O-benzoyl-2-deoxy-alpha-D-glucopyranoside (4) with penta-O-benzoyl-beta-D-galactopyranose (6) gave the derivative of beta-D-Galp-(1 --> 6)-alpha-D-GlcNAc 7 in 80% yield, This was glycosylated with penta-O-benzoyl-alpha,beta- D-galactofuranose (5>, employing the same catalyst, to afford the protected benzyl per-O-benzoyl-beta-D-Galf(1 --> 4)[beta-D-Galp(1 --> 6)]D-GlcNAc 10 in 41% yield, Alternatively, compound 10 was obtained directly in a one-pot reaction from 4, by sequential addition of 6 and 5 (34% yield). beta-Glycosidic linkages were diastereoselectively formed. De-O-benzoylation of 10, followed by heterogeneous catalytic transfer hydrogenolysis of the benzyl group afforded the free trisaccharide beta-D-Galf(1 --> 4)[beta-D-Galp(1 --> 6)]-D-GlcNAc (14) in 98% yield from 10. Sodium borohydride reduction of 14 gave the corresponding alditol, whose spectral data were identical to those reported for the alditol obtained from the 38-43 kDa cell-surface glycoprotein of Trypanosoma cruzi. (C) 1998 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00256-5

文献信息

• Glycosyl Azides – An Alternative Way to Disaccharides
  作者：Pavla Bojarová、Lucie Petrásková、Erica Elisa Ferrandi、Daniela Monti、Helena Pelantová、Marek Kuzma、Pavla Simerská、Vladimír Křen

  DOI：10.1002/adsc.200700028

  日期：2007.6.4

  good yields. The versatility of glycosyl azides was demonstrated in the synthesis of five disaccharides – two of them are described for the first time. All the reactions were highly regioselective, yielding β(16) isomers. β-Galactosidase from E. coli proved to have the best synthetic capabilities. The present study shows that glycosyl azides are a valuable alternative to common p-nitrophenyl glycoside

  糖基叠氮化物显示为β-半乳糖苷酶，β-葡萄糖苷酶和α-甘露糖苷酶的有效供体。仅α-半乳糖苷酶不能裂解各自的叠氮糖苷1，而且它们表现出竞争性抑制作用（尤其是来自黄萎病菌（Talaromyces flavus）的α-半乳糖苷酶）。高水溶性和糖基叠氮化物的现成合成即使具有困难的受体如N-乙酰基-D-甘露糖胺也能以高收率进行转糖基化反应。五个双糖的合成证明了糖基叠氮化物的多功能性–首次描述了其中的两个。所有反应都是高度区域选择性的，产生β（16）异构体。大肠杆菌的β-半乳糖苷酶被证明具有最佳的合成能力。本研究表明，在许多合成反应中，糖基叠氮化物是常见的对硝基苯基糖苷供体的一种有价值的替代物。