3'-galactosyl-lactose | 18404-79-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3'-galactosyl-lactose
• 英文别名: β-D-Galp-(1->3)-β-D-Galp-(1->4)-D-Glc；Gal(b1-3)Gal(b1-4)Glc；(2S,3R,4S,5R,6R)-2-[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 18404-79-0
• 化学式: C₁₈H₃₂O₁₆
• 分子量: 504.442
• InChiKey: ODDPRQJTYDIWJU-FFGMRWMPSA-N

物化性质

• 沸点：
  883.8±65.0 °C(Predicted)
• 密度：
  1.80±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -6.3
• 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

• 作为反应物：
  描述：

  乙酸酐 、 3'-galactosyl-lactose 在 吡啶 作用下， 反应 96.0h， 生成 (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-1,2,3,6-tetra-O-acetyl-D-glucopyranose
  参考文献：
  名称：

  Identification and synthesis of a trisaccharide produced from lactose by transgalactosylation

  摘要：

  Enzymatic transgalactosylation of lactose by means of Streptococcus thermophilus, subspecies DN-001065, led to a mixture of D-galactose (similar to 4%), D-glucose ( similar to 15%), lactose (similar to 51%), minor disaccharides (6%), trisaccharides ( similar to 20%) and tetrasaccharides (3%). The major trisaccharide ( similar to 16%) was identified by NMR spectroscopy and chemical synthesis as bring the known beta-D-galactopyranosyl-(1-->3)-beta-D-galactopyranosyl-(1-->4)-D-glucose (3'-beta-D-galactopyranosyl-lactose). It was purified from a mixture of peracetylated oligosaccharides by column chromatography followed by deacetylation. For the first time, 3'-beta-D-galactopyranosyl-lactose has been obtained on the 1 g scale, by resorting to simple techniques and equipment. NMR spectra have been unambiguously assigned. (C) 3000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00309-2
• 作为产物：
  描述：

  benzyl β-D-galactopyranosyl-(1->3)-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以98%的产率得到3'-galactosyl-lactose
  参考文献：
  名称：

  Identification and synthesis of a trisaccharide produced from lactose by transgalactosylation

  摘要：

  Enzymatic transgalactosylation of lactose by means of Streptococcus thermophilus, subspecies DN-001065, led to a mixture of D-galactose (similar to 4%), D-glucose ( similar to 15%), lactose (similar to 51%), minor disaccharides (6%), trisaccharides ( similar to 20%) and tetrasaccharides (3%). The major trisaccharide ( similar to 16%) was identified by NMR spectroscopy and chemical synthesis as bring the known beta-D-galactopyranosyl-(1-->3)-beta-D-galactopyranosyl-(1-->4)-D-glucose (3'-beta-D-galactopyranosyl-lactose). It was purified from a mixture of peracetylated oligosaccharides by column chromatography followed by deacetylation. For the first time, 3'-beta-D-galactopyranosyl-lactose has been obtained on the 1 g scale, by resorting to simple techniques and equipment. NMR spectra have been unambiguously assigned. (C) 3000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00309-2

文献信息

• Donor substrate promiscuity of bacterial β1–3-N-acetylglucosaminyltransferases and acceptor substrate flexibility of β1–4-galactosyltransferases
  作者：Yanhong Li、Mengyang Xue、Xue Sheng、Hai Yu、Jie Zeng、Vireak Thon、Yi Chen、Musleh M. Muthana、Peng G. Wang、Xi Chen

  DOI：10.1016/j.bmc.2016.02.043

  日期：2016.4

  beta4GalTs, donor substrate specificity studies of two bacterial beta3GlcNAcTs from Helicobacter pylori (Hpbeta3GlcNAcT) and Neisseria meningitidis (NmLgtA), respectively, using a library of 39 sugar nucleotides were carried out. The two beta3GlcNAcTs have complementary donor substrate promiscuity and 13 different trisaccharides were produced. They were used to investigate the acceptor substrate specificities

  beta1-3-N-乙酰氨基葡萄糖氨基转移酶（beta3GlcNAcTs）和beta1-4-半乳糖基转移酶（beta4GalTs）已广泛用于酶法合成含N-乙酰乳糖胺（LacNAc）的寡糖和包括聚LacNAc和乳糖（N-新四糖）的糖缀合物LNnT）存在于人类和其他哺乳动物的乳汁中。为了探索可以通过β3GlcNAcT和β4GalT的组合合成的寡糖和衍生物，分别使用39个糖核苷酸库对来自幽门螺杆菌（Hpbeta3GlcNAcT）和脑膜炎奈瑟氏球菌（NmLgtA）的两种细菌β3GlcNAcT的供体底物特异性进行了研究。执行。这两个beta3GlcNAcT具有互补的供体底物混杂，并产生了13种不同的三糖。他们分别用来研究三种脑膜炎奈瑟氏球菌（NmLgtB），幽门螺杆菌（Hpbeta4GalT）和牛（Bbeta4GalT）的beta4GalT的受体底物特异性。13种三糖中有10种被证明是这些beta4
• Engineering of the <i>Bacillus circulans</i> β-Galactosidase Product Specificity
  作者：Huifang Yin、Tjaard Pijning、Xiangfeng Meng、Lubbert Dijkhuizen、Sander S. van Leeuwen

  DOI：10.1021/acs.biochem.7b00032

  日期：2017.2.7

  the multiple biological functions of hMOS, it is important to broaden the variety of GOS structures. In this study, residue R484 near +1 subsite of the C-terminally truncated β-galactosidase from Bacillus circulans (BgaD-D) was subjected to site saturation mutagenesis. Especially the R484S and R484H mutant enzymes displayed significantly altered enzyme specificity, leading to a new type of GOS mixture

  微生物β-半乳糖苷酶在工业上被广泛用作从乳糖生产益生元低聚半乳糖（GOS）的生物催化剂。GOS混合物在婴儿配方食品中用作有益的添加剂，以模仿人乳寡糖（hMOS）的益生元作用。GOS混合物的结构多样性明显低于hMOS。由于这种结构复杂性被认为是hMOS多种生物学功能的基础，因此拓宽GOS结构的多样性非常重要。在这项研究中，来自圆形芽孢杆菌C末端截短的β-半乳糖苷酶+1亚位点附近的残基R484（BgaD-D）进行位点饱和诱变。特别是R484S和R484H突变酶显示出显着改变的酶特异性，从而导致一种新型的GOS混合物，其结构和键合类型也发生了改变。这些突变酶产生的GOS混合物含有14种在野生型GOS混合物中不存在的结构。其中10个是全新的结构。这些突变酶产生的GOS包含（β1→3）和（β1→4）键的组合，而野生型酶对（β1→4）键具有明显的偏好。三糖β- d -Gal p-（1→3）-β- d-
• Synthesis of oligosaccharides as potential novel food components and upscaled enzymatic reaction employing the β-galactosidase from bovine testes
  作者：Sven Schröder、Ulja Schmidt、Joachim Thiem、Jörg Kowalczyk、Markwart Kunz、Manfred Vogel

  DOI：10.1016/j.tet.2004.01.029

  日期：2004.3

  The β-galactosidase from bovine testes (EC 3.2.1.23) promotes the transfer of a galactose unit to glucose or galactose-containing residues in manifold derivatives, establishing β1→3 linkages.

  牛睾丸的β-半乳糖苷酶（EC 3.2.1.23）促进半乳糖单元向歧管衍生物中的葡萄糖或含半乳糖的残基转移，从而建立β1→3键。
• Structural Elucidation of Enzymatically Synthesized Galacto-oligosaccharides Using Ion-Mobility Spectrometry–Tandem Mass Spectrometry
  作者：Milica Carević、Dejan Bezbradica、Katarina Banjanac、Ana Milivojević、Mathieu Fanuel、Hélène Rogniaux、David Ropartz、Dušan Veličković

  DOI：10.1021/acs.jafc.6b01293

  日期：2016.5.11

  ingredients derived from lactose in a reaction catalyzed with β-galactosidases. Enzymatic transgalactosylation results in a mixture of compounds of various degrees of polymerization and types of linkages. Because structure plays an important role in terms of prebiotic activity, it is of crucial importance to provide an insight into the mechanism of transgalactosylation reaction and occurrence of different types

  低聚半乳糖（GOS）代表了一组不同的，由乳糖衍生的益生元，它们在β-半乳糖苷酶的催化反应中得到了衍生。酶促半乳糖基化导致各种聚合度和键类型的化合物的混合物。由于结构在益生元活性方面起着重要作用，因此至关重要的是，洞察半乳糖基化反应的机理以及在GOS合成过程中不同类型的β-键的发生。我们的研究证明，基于离子迁移谱-串联质谱（IMS-MS / MS）的一种新颖的一步方法可以完全阐明GOS结构。已经显示米曲霉的β-半乳糖苷酶对β-（1→3）或β-（1→6）键的形成具有最高的亲和力。另外，观察到在反应过程中不同键的发生变化，这表明可以通过适当控制酶促合成来实现具有改善的益生元活性的良好GOS结构的剪裁。
• 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。