methyl O-β-D-galactopyranosyl-O-(1<*>3)-β-D-galactopyranosyl-(1<*>3)-β-D-galactopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl O-β-D-galactopyranosyl-O-(1<*>3)-β-D-galactopyranosyl-(1<*>3)-β-D-galactopyranoside
• 英文别名: methyl β-D-galactopyranosyl-(1→3)-β-D-galactopyranosyl-(1→3)-β-D-galactopyranoside；β-(1-> 3)-D-Galp3OMe；Gal(b1-3)Gal(b1-3)b-Gal1Me；(2S,3R,4S,5R,6R)-2-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4S,5R,6R)-3,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-4-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₁₉H₃₄O₁₆
• 分子量: 518.469
• InChiKey: NSOQDZFOFNZQKY-FKWHSPGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.2
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  258
• 氢给体数：
  10
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  methyl O-(2,4,6-tri-O-benzoyl-β-D-galactopyranosyl)-(1<*>3)-O-(2,4,6-tri-O-benzoyl-β-D-galactopyranosyl)-(1<*>3)-2,4,6-tri-O-benzoyl-β-D-galactopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 methyl O-β-D-galactopyranosyl-O-(1<*>3)-β-D-galactopyranosyl-(1<*>3)-β-D-galactopyranoside
  参考文献：
  名称：

  General synthesis of (1 .fwdarw. 3)-.beta.-D-galacto oligosaccharides and their methyl .beta.-glycosides by a stepwise or a blockwise approach

  摘要：

  DOI：

  10.1021/jo00225a063

文献信息

• Regioselective Glycosylation of Unprotected Phenyl 1-Thioglycopyranosides with Phenylboronic Acid as a Transient Masking Group
  作者：Thomas Hauch Fenger、Robert Madsen

  DOI：10.1002/ejoc.201300723

  日期：2013.9

  A useful protocol is described for the regioselective glycosylation of the secondary alcohols in unprotected glycosyl acceptors. Phenyl 1-thioglycopyranosides derived from D-glucose, D-galactose, D-glucosamine, L-rhamnose, and L-fucose were treated with phenylboronic acid to install a temporary boronic ester, and then submitted to a Koenigs–Knorr glycosylation with perbenzoylated glucopyranosyl or galactopyranosyl

  描述了一个有用的协议，用于在未保护的糖基受体中对仲醇进行区域选择性糖基化。衍生自 D-葡萄糖、D-半乳糖、D-葡萄糖胺、L-鼠李糖和 L-岩藻糖的苯基 1-硫代吡喃糖苷用苯基硼酸处理以安装临时硼酸酯，然后用过苯甲酰化吡喃葡萄糖基进行 Koenigs-Knorr 糖基化或吡喃半乳糖基溴化物。与葡萄糖苷和半乳糖苷的 3-位偶联获得了良好的产率，但其他受体的产率较低。使用苯基 1-硫代-β-D-吡喃葡萄糖苷，也可以通过超臂硫代半乳糖苷供体实现偶联。来自葡萄糖-葡萄糖偶联的产物可以在 6 位进行第二次区域选择性糖基化。在半乳糖系列中，
• An exo-β-(1→3)-d-galactanase from Streptomyces sp. provides insights into type II arabinogalactan structure
  作者：Naomi X.-Y. Ling、Joanne Lee、Miriam Ellis、Ming-Long Liao、Shaio-Lim Mau、David Guest、Peter H. Janssen、Pavol Kováč、Antony Bacic、Filomena A. Pettolino

  DOI：10.1016/j.carres.2012.02.033

  日期：2012.5

  An exo-beta-(1 -> 3)-D-galactanase (SGalase1) that specifically cleaves the beta-(1 -> 3)-D-galactan backbone of arabinogalactan-proteins (AGPs) was isolated from culture filtrates of a soil Streptomyces sp. Internal peptide sequence information was used to clone and recombinantly express the gene in E. coli. The molecular mass of the isolated enzyme was similar to 45 kDa, similar to the 48.2 kDa mass predicted from the amino acid sequence. The pI, pH and temperature optima for the enzyme were similar to 7.45, 3.8 and 48 degrees C, respectively. The native and recombinant enzymes specifically hydrolysed beta-(1 -> 3)-D-galacto-oligo-or poly-saccharides from the upstream (non-reducing) end, typical of an exo-acting enzyme. A second homologous Streptomyces gene (SGalase2) was also cloned and expressed. SGalase2 was similar in size (47.9 kDa) and enzyme activity to SGalase1 but differed in its pH optimum (pH 5). Both SGalase1 and SGalase2 are predicted to belong to the CAZy glycosyl hydrolase family GH 43 based on activity, sequence homology and phylogenetic analysis. The K-m and V-max of the native exo-beta-(1 -> 3)-D-galactanase for de-arabinosylated gum arabic (dGA) were 19 mg/ml and 9.7 mu mol D-Gal/ min/mg protein, respectively. The activity of these enzymes is well suited for the study of type II galactan structures and provides an important tool for the investigation of the biological role of AGPs in plants. De-arabinosylated gum arabic (dGA) was used as a model to investigate the use of these enzymes in defining type II galactan structure. Exhaustive hydrolysis of dGA resulted in a limited number of oligosaccharide products with a trisaccharide of Gal(2)GlcA(1) predominating. (C) 2012 Elsevier Ltd. All rights reserved.
• General synthesis of (1 .fwdarw. 3)-.beta.-D-galacto oligosaccharides and their methyl .beta.-glycosides by a stepwise or a blockwise approach
  作者：Pavol Kovac、Richard B. Taylor、Cornelis P. J. Glaudemans

  DOI：10.1021/jo00225a063

  日期：1985.12