β-D-Galp-(1->3)-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->3)-D-Glc
• 英文别名: 3-O-beta-D-Galactopyranosyl-D-glucopyranose；(3R,4S,5R,6R)-6-(hydroxymethyl)-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2,3,5-triol
• 化学式: C₁₂H₂₂O₁₁
• 分子量: 342.3
• InChiKey: QIGJYVCQYDKYDW-SFOYIGFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  190
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  Lactose 在 acetate buffer 作用下， 反应 72.0h， 生成 β-D-Galp-(1->3)-D-Glc 、 6-O-β-D-galactopyranosyl-D-galactose 、 别乳糖 、 β-D-Galp-(1->3)-β-D-Galp-(1->3)-β-D-Galp-(1->3)-β-D-Galp-(1->4)-D-Glc
  参考文献：
  名称：

  Primary structure of ten galactosides formed by transglycosylation during lactose hydrolysis by Bifidobacterium bifidum

  摘要：

  Oligosaccharides formed by a transgalactosylation reaction during lactose hydrolysis with Bifidobacterium bifidum were separated into eight fractions by gel-permeation chromatography and their structures studies determined by trimethylsilylation analysis, methylation analysis, f.a.b.-m.s., g.l.c.-m.s. and enzymic hydrolysis as beta-D-Galp-(1----3)-D-Glc, beta-D-Galp-(1----6)-D-Glc, beta-D-Galp-(1----6)-D-Gal, beta-D-Galp-(1----3)-beta-D-Galp-(1----4)-D-Glc, beta-D-Galp-(1----6)[beta-D-Galp-(1----4)]-D-Glc, beta-D-Galp-(1----2)[beta-D-Galp-(1----6)]-D-Glc, beta-D-Galp-(1----3)-beta-D-Galp-(1----3)-beta-D-Galp-(1----4)-D-Glc, beta-D-Galp-(1----3)-beta-D-Galp-(1----3)-beta-D-Galp-(1----3)-beta-D-Ga lp- (1----4)-D-Glc, beta-D-Galp-(1----3)-beta-D-Galp-(1----3)-beta-DGalp-(1----3)-beta -D-Galp-(1----3)-beta-D-Galp-(1----4)-D-Glc, and beta-D-Galp-(1----3)-beta-D-Galp-(1----3)-beta-D-Galp-(1----3)-beta-D-Ga lp-(1----3)-beta-D-G-alp-(1----3) beta-D-Galp-(1----4)-D-Glc.

  DOI：

  10.1016/0008-6215(90)84228-m

文献信息

• 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.
• Primary structure of ten galactosides formed by transglycosylation during lactose hydrolysis by Bifidobacterium bifidum
  作者：Vincent Dumortier、Jean Montreuil、Stéphane Bouquelet

  DOI：10.1016/0008-6215(90)84228-m

  日期：1990.6

  Oligosaccharides formed by a transgalactosylation reaction during lactose hydrolysis with Bifidobacterium bifidum were separated into eight fractions by gel-permeation chromatography and their structures studies determined by trimethylsilylation analysis, methylation analysis, f.a.b.-m.s., g.l.c.-m.s. and enzymic hydrolysis as beta-D-Galp-(1----3)-D-Glc, beta-D-Galp-(1----6)-D-Glc, beta-D-Galp-(1----6)-D-Gal, beta-D-Galp-(1----3)-beta-D-Galp-(1----4)-D-Glc, beta-D-Galp-(1----6)[beta-D-Galp-(1----4)]-D-Glc, beta-D-Galp-(1----2)[beta-D-Galp-(1----6)]-D-Glc, beta-D-Galp-(1----3)-beta-D-Galp-(1----3)-beta-D-Galp-(1----4)-D-Glc, beta-D-Galp-(1----3)-beta-D-Galp-(1----3)-beta-D-Galp-(1----3)-beta-D-Ga lp- (1----4)-D-Glc, beta-D-Galp-(1----3)-beta-D-Galp-(1----3)-beta-DGalp-(1----3)-beta -D-Galp-(1----3)-beta-D-Galp-(1----4)-D-Glc, and beta-D-Galp-(1----3)-beta-D-Galp-(1----3)-beta-D-Galp-(1----3)-beta-D-Ga lp-(1----3)-beta-D-G-alp-(1----3) beta-D-Galp-(1----4)-D-Glc.