benzyl 3-O-(β-D-galactopyranosyl)-β-D-xylopyranoside | 138143-67-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 3-O-(β-D-galactopyranosyl)-β-D-xylopyranoside
• 英文别名: Gal(b1-3)Xyl(b)-O-Bn；(2S,3R,4S,5R,6R)-2-[(2R,3R,4S,5R)-3,5-dihydroxy-2-phenylmethoxyoxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 138143-67-6
• 化学式: C₁₈H₂₆O₁₀
• 分子量: 402.398
• InChiKey: VXEXMEROQCWUEY-FLSOLMFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  28
• 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：
  158
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  benzyl 3-O-(β-D-galactopyranosyl)-β-D-xylopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 水 为溶剂， 以1.4 g的产率得到O-β-D-galactopyranosyl (1-3)-D-xylose
  参考文献：
  名称：

  优化β-D-吡喃半乳糖基-D-木糖的酶促合成，以用于评估体内乳糖酶的活性。

  摘要：

  通过β-半乳糖苷酶催化反应获得二糖2-O-，3-O-和4-O-β-D-吡喃半乳糖基-D-木糖（分别为2、3和1），以用于评估体内肠道乳糖酶活性的测定。他们对乳鼠的给药，然后测定尿液中衍生的D-木糖，并测量肠匀浆中的乳糖酶活性，结果表明1是最适合用于检测肠道乳糖酶缺乏症的二糖。通过评估不同变量对酶促半乳糖基化反应的收率和区域选择性的影响，进一步研究了1的合成，并优化了纯化工艺。

  DOI：

  10.1016/j.bmc.2007.04.067
• 作为产物：
  描述：

  苄基-beta-D-木糖苷 、 尾-D-Galactoside,2-nitrophenyl(9CI) 在 Escherichia coli β-galactosidase 作用下， 以 phosphate buffer 为溶剂， 以1.9 g的产率得到benzyl 3-O-(β-D-galactopyranosyl)-β-D-xylopyranoside
  参考文献：
  名称：

  优化β-D-吡喃半乳糖基-D-木糖的酶促合成，以用于评估体内乳糖酶的活性。

  摘要：

  通过β-半乳糖苷酶催化反应获得二糖2-O-，3-O-和4-O-β-D-吡喃半乳糖基-D-木糖（分别为2、3和1），以用于评估体内肠道乳糖酶活性的测定。他们对乳鼠的给药，然后测定尿液中衍生的D-木糖，并测量肠匀浆中的乳糖酶活性，结果表明1是最适合用于检测肠道乳糖酶缺乏症的二糖。通过评估不同变量对酶促半乳糖基化反应的收率和区域选择性的影响，进一步研究了1的合成，并优化了纯化工艺。

  DOI：

  10.1016/j.bmc.2007.04.067

文献信息

• Enzymic .beta.-Galactosidation of Modified Monosaccharides: Study of the Enzyme Selectivity for the Acceptor and Its Application to the Synthesis of Disaccharides
  作者：Rosa Lopez、Alfonso Fernandez-Mayoralas

  DOI：10.1021/jo00083a013

  日期：1994.2

  The selectivity of the E. coli beta-galactosidase-catalyzed glycosylation of monosaccharides differently substituted at the anomeric position has been studied. Substituents bearing a phenyl ring increase the enzyme-acceptor binding; however, partial enzyme inhibition occurs. The regioselectivity of the glycosylation was dependent on small variations in the monosaccharide accceptor, such as the atom linked to the anomeric carbon and the number of methylenes between this atom and aromatic ring. A schematic model is proposed that accounts for the results. The information from this study allows the direct synthesis of disaccharides, with high regioselectivity and yields ranging from 30 to 40%.
• Enzymatic syntheses and selective hydrolysis of O-β-d-galactopyranosides using a marine mollusc β-galactosidase
  作者：Assunta Giordano、Annabella Tramice、Giuseppina Andreotti、Ernesto Mollo、Antonio Trincone

  DOI：10.1016/j.bmcl.2004.10.016

  日期：2005.1

  The use of crude extract of the hepatopancreas of Aplysia fasciata, a large mollusc belonging to the order Anaspidea containing a beta-galactosidase activity, was reported for the synthesis of different galactosides. Good yields with polar acceptors and the uncommon beta-1-3 selectivity in the transgalactosylation reactions with most of the acceptors were observed. A beta-1-2 selectivity in the hydrolytic conditions was also observed and discussed. (C) 2004 Elsevier Ltd. All rights reserved.
• Controlling yield and regioselectivity in the enzymatic synthesis of β-D-galactopyranosyl-β-D-xylopyranosides
  作者：Rosa López、Alfonso Fernández-Mayoralas

  DOI：10.1016/s0040-4039(00)79118-0

  日期：1992.9

  Yield and regioselectivity of the galactosidation of beta-D-xylopyranosides catalysed by the beta-galactosidase from E. coli can be modulated by the nature of the aglyconic moiety of the xylopyranosides.
• Optimizing the enzymatic synthesis of β-d-galactopyranosyl-d-xyloses for their use in the evaluation of lactase activity in vivo
  作者：Carmen Hermida、Guillermo Corrales、Francisco J. Cañada、Juan J. Aragón、Alfonso Fernández-Mayoralas

  DOI：10.1016/j.bmc.2007.04.067

  日期：2007.7

  their use in the evaluation of intestinal lactase activity in vivo. Their administration to suckling rats followed by determination of the derived D-xylose in the urine and measurement of lactase activity in intestinal homogenates showed 1 to be the most suitable disaccharide for a potential test of the deficiency of intestinal lactase. The synthesis of 1 was further studied by evaluating the effect of

  通过β-半乳糖苷酶催化反应获得二糖2-O-，3-O-和4-O-β-D-吡喃半乳糖基-D-木糖（分别为2、3和1），以用于评估体内肠道乳糖酶活性的测定。他们对乳鼠的给药，然后测定尿液中衍生的D-木糖，并测量肠匀浆中的乳糖酶活性，结果表明1是最适合用于检测肠道乳糖酶缺乏症的二糖。通过评估不同变量对酶促半乳糖基化反应的收率和区域选择性的影响，进一步研究了1的合成，并优化了纯化工艺。