β-D-Galp-(1->4)-β-D-Galp-(1->4)-α-D-Glcp | 121153-20-6

• 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->4)-β-D-Galp-(1->4)-α-D-Glcp
• 英文别名: β-D-galactopyranosyl-(1→4)-β-D-galactopyranosyl-(1→4)-α-D-glucopyranose；β-D-galactopyranosyl-(1→4)-β-D-galactopyranosyl-(1→4)-α-D-glucose；Gal-β(1→4)-Gal-β(1→4)-αGlc；O-β-D-Galactopyranosyl-(1->4)-O-β-galactopyranosyl-(1->4)-D-glucose；Gal(b1-4)Gal(b1-4)a-Glc；(2S,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(2R,3S,4R,5R,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 121153-20-6
• 化学式: C₁₈H₃₂O₁₆
• 分子量: 504.442
• InChiKey: FYGDTMLNYKFZSV-DYFSSTQOSA-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

• 作为反应物：
  描述：

  β-D-Galp-(1->4)-β-D-Galp-(1->4)-α-D-Glcp 、 氨基硫脲 在 sodium cyanoborohydride 作用下， 以 水 为溶剂， 反应 72.0h， 生成
  参考文献：
  名称：

  Hybrid immobilization of galactosyl lactose and cellobiose on a gold substrate to modulate biological responses

  摘要：

  Bioactive O-beta-D-galactopyranosyl-(1 -> 4)-O-beta-D-galactopyranosyl-(1 -> 4)-D-glucopyranose (4'-galactosyl lactose) was site-selectively modified at a reducing end with thiosemicarbazide (TSC). As-synthesized 4'-galactosyl lactose-TSC was immobilized on a gold substrate with cellobiose-TSC as a spacer through spontaneous self-assembly chemisorption via S-Au bonding. Quartz crystal microbalance analysis suggested the successful formation of self-assembled monolayers (SAMs) of 4'-galactosyl lactose-TSC and/or cellobiose-TSC. Galactose-binding lectin exhibited the highest affinity for hybrid SAMs with an equimolar ratio of the two oligosaccharide-TSCs, while glucose-binding lectin showed decreasing adsorption with a decrease in cellobiose-TSC ratios. Human hepatocellular carcinoma cells, which recognize galactose residues, efficiently adhered to the hybrid SAMs. Higher enzymatic deethoxylation of ethoxyresorufin via cytochrome P450 appeared on hybrid SAMs. These results suggested that clustering of the bioactive sugars was involved in the cellular responses, possibly via biological carbohydrate-protein interactions. This approach to designing carbohydrate-based scaffolds should provide a basis for the functional development of glyco-decorated biointerfaces for cell culture applications. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carbpol.2012.09.088
• 作为产物：
  描述：

  在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 生成 β-D-Galp-(1->4)-β-D-Galp-(1->4)-α-D-Glcp 、 4-Galactosyllactose
  参考文献：
  名称：

  Gram-scale chemical synthesis of galactosyllactoses and their impact on infant gut microbiota in vitro

  摘要：

  我们报告了从乳糖出发，以克为单位化学合成 3′-、4′- 和 6′-半乳糖的过程。我们利用婴儿粪便样本进行了发酵实验，在体外测试了这些半乳糖对婴儿肠道微生物群的影响。

  DOI：

  10.1039/d3ob02069j

文献信息

• Präparat zur Wirkstoffapplikation in Kleinsttröpfchenform
  申请人：Cevc, Gregor, Prof. Dr.

  公开号：EP0475160A1

  公开（公告）日：1992-03-18

  Die Erfindung betrifft ein Präparat zur Applikation von Wirkstoffen in Form kleinster, insbesondere mit einer membranartigen Hülle aus einer oder wenigen Lagen amphiphiler Moleküle bzw. mit einer amphiphilen Trägersubstanz versehenen Flüssigkeitströpfchen, insbesondere zum Transport des Wirkstoffes in und durch natürliche Barrieren und Konstriktionen wie Häute und dergleichen. Das Präparat weist einen Gehalt einer randaktiven Substanz auf, der bis zu 99 Mol.-% des Gehaltes dieser Substanz entspricht, durch den der Solubilisierungspunkt der Tröpfchen erreicht wird. Das Präparat eignet sich zur nichtinvasiven Verabreichung von Antidiabetica, insbesondere von Insulin. Die Erfindung betrifft außerdem ein Verfahren zur Herstellung solcher Präparate.

  本发明涉及一种以微小液滴形式施用活性物质的制剂，特别是具有一层或几层两亲性分子或两亲性载体物质的膜状包膜，尤其是用于将活性物质输送到或通过皮肤等天然屏障和收缩物。制剂中边缘活性物质的含量最高可达 99 摩尔%，从而达到液滴的溶解点。该制剂适用于非侵入性给药抗糖尿病药物，特别是胰岛素。本发明还涉及生产这种制剂的工艺。
• Protein particles for therapeutic and diagnostic use
  申请人：——

  公开号：US20020142046A1

  公开（公告）日：2002-10-03

  Albumin particles in the nanometer and micrometer size range in an aqueous suspension are rendered stable against resolubilization without the aid of a cross-linking agent and witout denaturation, by the incorporation of a stabilizing agent in the particle composition. Stabilizing agents disclosed include reducing agents, oxdizing agents, hydrogen-accepting molecules, high molecular weight polymers, and sulfur-containing ring compounds. Also disclosed are fibrinogen-coated particles, cross-linked or non-cross-linked, and their use as co-aggregants with platelets and with themselves for purposes of shortening bleeding time and enhancing the effect of thrombin.

  通过在颗粒组合物中加入稳定剂，可使水悬浮液中纳米和微米大小的白蛋白颗粒在不借助交联剂和不发生变性的情况下稳定地防止溶解。已公开的稳定剂包括还原剂、氧化剂、氢接受分子、高分子量聚合物和含硫环化合物。此外，还公开了交联或非交联的纤维蛋白原涂层微粒，以及它们作为与血小板和自身的共聚物的用途，以达到缩短出血时间和增强凝血酶效果的目的。
• Enzymatic synthesis of 3-aminopropyl-1-<i>O</i>-β-<scp>D</scp>-galactopyranoside catalyzed by<i>Aspergillus oryzae</i>β-galactosidase
  作者：Cecilia Porciúncula González、Ernesto Rodríguez、Silvia Soule、Laura Franco Fraguas、Beatriz M. Brena、Cecilia Giacomini、Gabriela Irazoqui

  DOI：10.3109/10242422.2015.1095678

  日期：2015.7.4

  Glycosidases represent excellent green chemistry alternatives as catalysts for the synthesis of glycosides, and in particular their stereoselectivity allows the production of anomerically pure glycosides, in only one reaction step using mild reaction conditions. Here, we report the enzymatic synthesis and structural characterization of 3-aminopropyl-1-O--D-galactopyranoside. Optimal reaction conditions for the transgalactosylation reaction were 100mM lactose, 500mM 3-amino-1-propanol and 24 h of incubation at 50 degrees C with 6 U/mL of -galactosidase from Aspergillus oryzae. The fact that the synthesis of 1-propyl-2-O--D-galactopyranoside using 1-amino-2-propanol as acceptor was not achieved, and that N-glycoside formation was not observed, confirms the selectivity of -galactosidase for the synthesis of O-glycosides, and particularly for primary alcohols. The synthesized galactosides were evaluated for their ability to interact with bovine spleen galectin-1 (Gal-1) by using the hemagglutination inhibition assay; results demonstrated that 3-aminopropyl-1-O--D-galactopyranoside may be considered as a functionalized galactose moiety more than an efficient Gal-1 inhibitor. The proposed approach constitutes a promising tool for the generation of glycopolymers and glyconanoparticles with potential applications in the development of biosensors as well as construction blocks in chemical synthesis.
• US5616311A
  申请人：——

  公开号：US5616311A

  公开（公告）日：1997-04-01
• US5725804A
  申请人：——

  公开号：US5725804A

  公开（公告）日：1998-03-10