β-D-Galp-(1->6)-β-D-Galp-(1->4)-D-Glc

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-Galp-(1->6)-β-D-Galp-(1->4)-D-Glc
• 英文别名: Gal(b1-6)Gal(b1-4)Glc；(2R,3R,4S,5R,6R)-2-(hydroxymethyl)-6-[[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-2-yl]methoxy]oxane-3,4,5-triol
• 化学式: C₁₈H₃₂O₁₆
• 分子量: 504.442
• InChiKey: OWEGMIWEEQEYGQ-JVOFLGKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.9
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  269
• 氢给体数：
  11
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  Lactose 在 β-galactosidase from Aspergillus oryzae 作用下， 反应 2.0h， 生成 β-D-Galp-(1->6)-β-D-Galp-(1->4)-D-Glc
  参考文献：
  名称：

  非天然三糖和半乳糖苷的酶促合成；与半乳糖凝集素相互作用的洞察力，取决于它们的结构

  摘要：

  半乳凝素是碳水化合物识别蛋白的一个家族，通过与特定的糖表位相互作用，可以介导重要的生物学过程，包括免疫细胞稳态和致耐受性回路的激活。在该家族的不同成员中，半乳凝集素1和3已显示出促肿瘤作用，在多种赘生性疾病中过表达，被证明与肿瘤免疫逃逸，肿瘤进展和对药物诱导的细胞凋亡的抵抗有关。因此，通过阻断其碳水化合物识别结构域可以抑制其促肿瘤发生能力的特定糖苷的产生是该领域当前的主要挑战之一。考虑到半乳凝素与配体的结合强度与配体结构密切相关，这种关系的分析为合理设计可以用作有效半乳糖凝集素抑制剂的高亲和力配体提供了有价值的信息。利用糖苷酶催化转糖基化反应的能力，我们实现了酶促合成β-d-Galp-（1→6）-β-d-Galp-（1→4）-d-Glcp（2）的混合物β-d-Galp-（1→6）-β-d-Glcp-（1→4）-d-Glcp（5）和β-d-Galp-（1→3）-β-d-Glcp- （1→4）

  DOI：

  10.1016/j.carres.2018.10.011

文献信息

• 人乳三糖半乳糖基乳糖的制备
  申请人：天津科技大学

  公开号：CN114920788A

  公开（公告）日：2022-08-19

  本发明提供三种天然等同人乳三糖半乳糖基乳糖，3′‑半乳糖基乳糖，4′‑半乳糖基乳糖和6′‑半乳糖基乳糖及其合成中间体的制备方法。半乳糖基乳糖在母乳中尤其是初乳中含量较高，其具有调节婴儿肠道微生物平衡，影响肠上皮细胞以及预防和治疗肠道炎症方面的潜在药物作用，在营养、食品以及医药领域具有良好的应用潜力。
• Method for removing residual organic solvent from a crystalline oligosaccharide
  申请人：Glycom A/S

  公开号：US11384110B2

  公开（公告）日：2022-07-12

  The present invention relates to a method of removing residual organic solvent from crystalline oligosaccharides by the use of water vapour as well as the pharmaceutically and nutritionally suitable crystalline oligosaccharides obtained by said method.

  本发明涉及一种利用水蒸气去除结晶低聚糖中残留有机溶剂的方法，以及通过该方法获得的具有药用和营养价值的结晶低聚糖。
• Production of Galacto-oligosaccharides by the β-Galactosidase from Kluyveromyces lactis: Comparative Analysis of Permeabilized Cells versus Soluble Enzyme
  作者：Barbara Rodriguez-Colinas、Miguel A. de Abreu、Lucia Fernandez-Arrojo、Roseri de Beer、Ana Poveda、Jesus Jimenez-Barbero、Dietmar Haltrich、Antonio O. Ballesteros Olmo、Maria Fernandez-Lobato、Francisco J. Plou

  DOI：10.1021/jf2022012

  日期：2011.10.12

  The transgalactosylation activity of Kluyveromyces lactis cells was studied in detail. Cells were permeabilized with ethanol and further lyophilized to facilitate the transit of substrates and products. The resulting biocatalyst was assayed for the synthesis of galacto-oligosaccharides (GOS) and compared with two soluble beta-galactosidases from K. lactis (Lactozym 3000 L HP G and Maxilact LGX 5000). Using 400 g/L lactose, the maximum GOS yield, measured by HPAEC-PAD analysis, was 177 g/L (44% w/w of total carbohydrates). The major products synthesized were the disaccharides 6-galactobiose [Gal-beta(1 -> 6)-Gal] and allolactose [Gal-beta(1 -> 6)-Glc], as well as the trisaccharide 6-galactosyl-lactose [Gal-beta(1 -> 6)-Gal-beta(1 -> 4)-Glc], which was characterized by MS and 2D NMR. Structural characterization of another synthesized disaccharide, Gal-beta(1 -> 3)-Glc, was carried out. GOS yield obtained with soluble beta-galactosidases was slightly lower (160 g/L for Lactozym 3000 L HP G and 154 g/L for Maxilact LGX 5000); however, the typical profile with a maximum GOS concentration followed by partial hydrolysis of the newly formed oligosaccharides was not observed with the soluble enzymes. Results were correlated with the higher stability of beta-galactosidase when permeabilized whole cells were used.
• β-Galactosidase from Lactobacillus plantarum WCFS1: biochemical characterization and formation of prebiotic galacto-oligosaccharides
  作者：Sanaullah Iqbal、Thu-Ha Nguyen、Tien Thanh Nguyen、Thomas Maischberger、Dietmar Haltrich

  DOI：10.1016/j.carres.2010.03.028

  日期：2010.7

  Recombinant beta-galactosidase from Lactobacillus plantarum WCFS1, homologously over-expressed in L plantarum, was purified to apparent homogeneity using p-aminobenzyl 1-thio-beta-D-galactopyranoside affinity chromatography and subsequently characterized. The enzyme is a heterodimer of the LacLM-family type, consisting of a small subunit of 35 kDa and a large subunit of 72 kDa. The optimum pH for hydrolysis of its preferred substrates o-nitrophenyl-beta-D-galactopyranoside (oNPG) and lactose is 7.5 and 7.0, and optimum temperature for these reactions is 55 and 60 degrees C, respectively. The enzyme is most stable in the pH range of 6.5-8.0. The K-m, k(cat) and k(cat)/K-m values for oNPG and lactose are 0.9 mM, 92 s(-1), 130 mM(-1) s(-1) and 29 mM, 98 s(-1),3.3 mM(-1) s(-1), respectively. The L. plantarum beta-galactosidase possesses a high transgalactosylation activity and was used for the synthesis of prebiotic galacto-oligosaccharides (GOS). The resulting GOS mixture was analyzed in detail, and major components were identified by using high performance anion exchange chromatography with pulsed amperometric detection (HPAEC-PAD) as well as capillary electrophoresis. The maximal GOS yield was 41% (w/w) of total sugars at 85% lactose conversion (600 mM initial lactose concentration). The enzyme showed a strong preference for the formation of beta-(1 -> 6) linkages in its transgalactosylation mode, while beta-(1 -> 3)-linked products were formed to a lesser extent, comprising similar to 80% and 9%, respectively, of the newly formed glycosidic linkages in the oligosaccharide mixture at maximum GOS formation. The main individual products formed were beta-D-Galp-(1 -> 6)-D-Lac, accounting for 34% of total GOS, and beta-D-Galp-(1 -> 6)-D-Glc, making up 29% of total GOS. (C) 2010 Elsevier Ltd. All rights reserved.
• Production of a new sucrose derivative by transglycosylation of recombinant Sulfolobus shibatae β-glycosidase
  作者：Na-Young Park、Nam-In Baek、Jaeho Cha、Soo-Bok Lee、Joong-Hyuck Auh、Cheon-Seok Park

  DOI：10.1016/j.carres.2005.02.003

  日期：2005.5

  The gene encoding beta-glycosidase of the hyperthermophilic archaea Sulfolobus shibatae (SSG) was expressed in Escherichia coli. Recombinant SSG (referred to as rSSG hereafter) was efficiently purified, and its transglycosylation activity was tested with lactose as a donor and various sugars as acceptors. When sucrose was used as an acceptor, we found a distinct intermolecular transglycosylation product and confirmed its presence by TLC and high performance anion exchange chromatography (HPAEC). The sucrose transglycosylation product was isolated by paper chromatography, and its chemical structure was determined by H-1 and C-13 NMR. The sucrose transfer product was determined to be beta-D-galactopyranosyl-(1 -> 6)-alpha-D-glucopyranosyl-beta-D-fructofuranoside with a galactose molecule linked to sucrose via a beta-(1 -> 6)-glycosidic bond. (c) 2005 Elsevier Ltd. All rights reserved.