phenyl 4-O-(β-D-galactopyranosyl)-β-D-glucopyranoside | 100678-97-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 4-O-(β-D-galactopyranosyl)-β-D-glucopyranoside
• 英文别名: phenyl β-lactoside；β-Phenyllactosid；phenyl (β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside；Phenyl-β-lactosid；Gal(b1-4)Glc(b)-O-Ph；(2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-phenoxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 100678-97-5
• 化学式: C₁₈H₂₆O₁₁
• 分子量: 418.398
• InChiKey: TYALKKBMRDZWLW-MUKCROHVSA-N

物化性质

• 熔点：
  190.5-191.5 °C
• 沸点：
  714.6±60.0 °C(Predicted)
• 密度：
  1.60±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  179
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  phenyl 4-O-(β-D-galactopyranosyl)-β-D-glucopyranoside 在 palladium on activated charcoal N-溴代丁二酰亚胺(NBS) 、 4 A molecular sieve 、 氢气 、 sodium methylate 、 对甲苯磺酸 、 barium carbonate 作用下， 以 吡啶 、 甲醇 、 四氯化碳 、 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 4-O-(6-deoxy-β-D-galactopyranosyl)-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
• 作为产物：
  描述：

  1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 在 4 A molecular sieve 、 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 phenyl 4-O-(β-D-galactopyranosyl)-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

• Stereoselective enzymatic galactosylation of C-glucosides
  作者：Luigi Panza、Pietro L. Chiappini、Giovanni Russo、Daniela Monti、Sergio Riva

  DOI：10.1039/a701747b

  日期：——

  The enzyme β-1,4-galactosyl transferase from bovine colostrum (GalT) is able stereoselectively to galactosylate C-glucosides (i.e. 1 and 4), precursors of stable glycoconjugate analogues, and a systematic investigation of the structural modifications at C-1 and/or C-5 of the glycosides that can be accepted by this enzyme has been undertaken, adding information to the currently accepted model of substrate binding into the GalT active site.

  牛初乳中的β-1,4-半乳糖基转移酶（GalT）能够立体选择性地半乳糖基化C-葡萄糖苷（即1和4）--稳定的糖苷类似物的前体--并对该酶可接受的糖苷的C-1和/或C-5结构修饰进行了系统研究，为目前公认的底物结合到GalT活性位点的模型增添了信息。
• Fluorescence Activated Cell Sorting as a General Ultra-High-Throughput Screening Method for Directed Evolution of Glycosyltransferases
  作者：Guangyu Yang、Jamie R. Rich、Michel Gilbert、Warren W. Wakarchuk、Yan Feng、Stephen G. Withers

  DOI：10.1021/ja104167y

  日期：2010.8.4

  Glycosyltransferases (GTs) offer very attractive approaches to the synthesis of complex oligosaccharides. However, the limited number of available GTs, together with their instability and strict substrate specificity, have severely hampered the broad application of these enzymes. Previous attempts to broaden the range of substrate scope and to increase the activity of GTs via protein engineering have met with

  糖基转移酶 (GT) 为合成复杂的寡糖提供了非常有吸引力的方法。然而，可用的 GT 数量有限，加上它们的不稳定性和严格的底物特异性，严重阻碍了这些酶的广泛应用。以前通过蛋白质工程扩大底物范围和增加 GT 活性的尝试取得了有限的成功，部分原因是缺乏有效的高通量筛选方法。最近，我们报道了一种基于荧光激活细胞分选的唾液酸转移酶超高通量筛选方法 (Aharoni et al. Nat. Methods 2006, 3, 609-614)。这里，我们通过引入双色筛选方案大大改进了这种方法，以最大限度地减少假阳性突变体的可能性，并通过中性糖转移酶、β-1,3-半乳糖基转移酶 CgtB 的定向进化证明其普遍性。从 > 10(7) CgtB 突变体库中快速鉴定出一种比野生型酶具有更广泛底物耐受性和 300 倍高活性的变体。重要的是，与母体酶相比，该变体能更有效地合成 G(M1a) 和去唾液酸 G(M1)
• The Alkaline Degradation of Phenyl-β-lactoside, Phenyl-β-cellobioside and Phenyl-D-gluco-β-D-gulo-heptoside
  作者：Edna M. Montgomery、Nelson K. Richtmyer、C. S. Hudson

  DOI：10.1021/ja01250a018

  日期：1943.10
• Helferich; Griebel, Justus Liebigs Annalen der Chemie, 1940, vol. 544, p. 191,201
  作者：Helferich、Griebel

  DOI：——

  日期：——
• 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.