2'-O-fucosyllactose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-O-fucosyllactose
• 英文别名: 2'-fucosyllactose；2’-fucosyllactose；2′-fucosyllactose；2′-FL；Fuc(a1-2)Gal(b1-4)Glc；(2S,3S,4R,5S,6S)-2-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• 化学式: C₁₈H₃₂O₁₅
• 分子量: 488.443
• InChiKey: SNFSYLYCDAVZGP-OLAZETNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.8
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  248
• 氢给体数：
  10
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  2'-O-fucosyllactose 在 碳酸氢铵 作用下， 以 甲醇 为溶剂， 反应 48.0h， 生成 (2S,3S,4R,5S,6S)-2-(((2S,3R,4S,5R,6R)-2-(((2R,3S,4R,5R,6R)-6-amino-4,5-dihydroxy-2-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)oxy)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)oxy)-6-methyltetrahydro-2H-pyran-3,4,5-triol
  参考文献：
  名称：

  在生物膜根除中利用立体电子效应：扫描电子显微镜观察到的合成 β-氨基人乳低聚糖阻碍微生物粘附

  摘要：

  与 Edward 一起，Lemieux 是最早研究负超共轭（即异头效应）或偏爱碳水化合物中 C1-O5 键的 gauche 构象的研究人员之一。Lemieux 还研究了一种深奥的理论，即使没有争议，也被称为反向异头效应 (RAE)。该理论用于合理化预测的异头稳定不发生的场景。一个这样的例子是 Kochetkov 胺化，其中还原性末端胺仅作为 β-端基异构体存在。在此，我们简要介绍了 Lemieux 在立体电子学领域的贡献，并将这些知识应用于 β-氨基人乳寡糖 (βA-HMO) 的合成。评估了这些分子在 B 组链球菌 (GBS) 和金黄色葡萄球菌。虽然亲本 HMO 缺乏抗菌和抗生物膜活性，但它们的 β-氨基衍生物显着抑制了两种物种的生物膜形成。场发射枪扫描单电子显微镜 (FEG-SEM) 显示，用 β-氨基 HMO 处理可显着抑制细菌粘附并消除两种微生物形成生物膜的能力。

  DOI：

  10.1021/acs.joc.0c01958
• 作为产物：
  描述：

  guanosine 5'-diphospho-D-mannose 在 GDP-4-keto-6-deoxy-D-mannose 3,5-epimerase-4-reductase 、 GDP-D-mannose 4,6-dehydratase 、 GT-FucT₂ 、 三羟甲基氨基甲烷盐酸盐 、 还原型辅酶II(NADPH)四钠盐 、 magnesium chloride 、 manganese(ll) chloride 作用下， 以 phosphate buffer 、 水 为溶剂， 反应 10.0h， 生成 2'-O-fucosyllactose
  参考文献：
  名称：

  Synthesis of the milk oligosaccharide 2′-fucosyllactose using recombinant bacterial enzymes

  摘要：

  The enzymatic synthesis of GDP-P-L-fucose and its enzymatic transfer reaction using recombinant enzymes from bacterial sources was examined. The GDP-D-mannose 4,6-dehydratase and the GDP-4-keto-6-deOXY-D-mannose 3,5-epimerase-4-reductase from Escherichia coli K-12, respectively, were used to catalyse the conversion of GDP-alpha -D-mannose to GDP-beta -L-fucose with 78% yield. For the transfer of the L-fucose to an acceptor, we cloned and overproduced the alpha-(1 --> 2)-fucosyltransferase (FucT2) protein from Helicobacter pylori. We were able to synthesise 2 ' -fucosyllactose using the overproduced FucT2 enzyme, enzymatically synthesised GDP-L-fucose and lactose. The isolation of 2 ' -fucosyllactose was accomplished by anion-exchange chromatography and gel filtration to give 65% yield. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00177-x

文献信息

• Unprecedented Affinity Labeling of Carbohydrate-Binding Proteins with <i>s</i>-Triazinyl Glycosides
  作者：Arnaud Masselin、Antoine Petrelli、Maxime Donzel、Sylvie Armand、Sylvain Cottaz、Sébastien Fort

  DOI：10.1021/acs.bioconjchem.9b00432

  日期：2019.9.18

  Carbohydrate–protein interactions trigger a wide range of biological signaling pathways, the mainstays of physiological and pathological processes. However, there are an incredible number of carbohydrate-binding proteins (CBPs) that remain to be identified and characterized. This study reports for the first time the covalent labeling of CBPs by triazinyl glycosides, a new and promising class of affinity-based glycoprobes. Mono- and bis-clickable triazinyl glycosides were efficiently synthesized from unprotected oligosaccharides (chitinpentaose and 2′-fucosyl-lactose) in a single step. These molecules allow the specific covalent labeling of chitin-oligosaccharide-binding proteins (wheat germ agglutinin WGA and Bc ChiA1 D202A, an inactivated chitinase) and fucosyl-binding lectin (UEA-I), respectively.

  碳水化合物与蛋白质之间的相互作用引发了一系列生物信号通路，这些通路是生理和病理过程的支柱。然而，仍有数量惊人的碳水化合物结合蛋白（CBPs）有待鉴定和表征。本研究首次报道了用三嗪基糖苷对 CBPs 进行共价标记的方法，三嗪基糖苷是一类新型的、前景广阔的亲和性糖探针。研究人员从无保护的低聚糖（甲壳素五糖和 2′-岩藻糖基-乳糖）中高效合成了单咔唑和双咔唑三嗪糖苷。这些分子可分别对几丁质寡糖结合蛋白（小麦胚芽凝集素 WGA 和 Bc ChiA1 D202A，一种失活的几丁质酶）和岩藻糖结合凝集素（UEA-I）进行特异性共价标记。
• [EN] MULTIVALENT OLIGOSACCHARIDES<br/>[FR] OLIGOSACCHARIDES MULTIVALENTS
  申请人：NAT UNIV IRELAND

  公开号：WO2013004669A1

  公开（公告）日：2013-01-10

  Helicobacter pylori infects over half of the world's population and thought to be a leading cause of chronic gastritis, peptic ulcer, and gastric cancer. Campylobacterjejuni is another enteric and gastric bacteria which is the most common cause of bacterial diarrhoea. Both of these microbes adhere to mucosa by binding blood group antigen-related or other carbohydrates expressed on epithelial cells. Breast feeding protects infants against these bacterial infections, which was proven to be a consequence of the presence of large quantities of antigen oligosaccharides in human milk. Multivalent oligosaccharides were synthesized with rigid and flexible scaffolds designed to present the carbohydrates diversely. These compounds were evaluated on purified chicken large intestine mucin. Some of the compounds inhibit the binding of bacteria to the mucin. These multivalent oligosaccharides are promising prophylactic and therapeutic antimicrobial agents for gastric and intestinal diseases.

  幽门螺杆菌感染全球超过一半的人口，被认为是慢性胃炎、消化性溃疡和胃癌的主要原因之一。弯曲菌属是另一种肠道和胃部细菌，是细菌性腹泻最常见的原因。这两种微生物通过与上皮细胞表达的血型抗原相关或其他碳水化合物结合，附着在粘膜上。母乳喂养可以保护婴儿免受这些细菌感染，这是因为人乳中存在大量抗原寡糖。多价寡糖通过设计刚性和灵活的支架合成，以多样化呈现碳水化合物。这些化合物在纯化的鸡大肠粘膜上进行评估，其中一些化合物可以抑制细菌与粘膜的结合。这些多价寡糖是胃肠道疾病的有希望的预防和治疗抗菌剂。
• Bi- to tetravalent glycoclusters: synthesis, structure–activity profiles as lectin inhibitors and impact of combining both valency and headgroup tailoring on selectivity
  作者：Guan-Nan Wang、Sabine André、Hans-Joachim Gabius、Paul V. Murphy

  DOI：10.1039/c2ob25870f

  日期：——

  The emerging functional versatility of cellular glycans makes research on the design of synthetic inhibitors a timely topic. In detail, the combination of ligand (or headgroup or contact site) structure with spatial parameters that depend on topological and geometrical factors underlies the physiological selectivity of glycan-protein (lectin) recognition. We herein tested a panel of bi-, tri- and tetravalent compounds against two plant agglutinins and adhesion/growth-regulatory lectins (galectins). In addition, we examined the impact of headgroup tailoring (converting lactose to 2′-fucosyllactose) in combination with valency increase in two assay types of increasing biorelevance (from solid-phase binding to cell binding). Compounds were prepared using copper-catalysed azide alkyne cycloaddition from peracetylated lactosyl or 2′-fucosyllactosyl azides. Significant inhibition was achieved for the plant toxin with a tetravalent compound. Different levels of sensitivity were noted for the three groups of the galectin family. The headgroup extension to 2′-fucosyllactose led to a selectivity gain, especially for the chimera-type galectin-3. Valency increase established discrimination against the homodimeric proteins, whereas the combination of valency with the headgroup extension led to discrimination against the tandem-repeat-type galectin-8 for chicken galectins but not human galectins-3 and -4. Thus, detailed structure–activity profiling of glycoclusters combined with suitably modifying the contact site for the targeted lectin will help minimize cross-reactivity among this class of closely related proteins.

  细胞糖类日益显现的功能多样性使得合成抑制剂设计的研究成为一个及时的话题。具体而言，配体（或头基或接触位点）结构与依赖于拓扑和几何因素的空间参数的结合构成了糖类-蛋白质（凝集素）识别的生理选择性。本文测试了一系列二价、三价和四价化合物，以针对两种植物凝集素和粘附/生长调节凝集素（伽星素）。此外，我们还研究了头基调节（将乳糖转化为2'-呋喃乳糖）与在两个生物相关性的测定类型中增加价态的结合影响（从固相结合到细胞结合）。化合物通过铜催化的叠氮炔烃环加成反应，从过乙酰化的乳糖基或2'-呋喃乳糖基叠氮化物制备而成。使用四价化合物对植物毒素实现了显著的抑制。伽星素家族的三个组别表现出不同程度的敏感性。将头基延伸至2'-呋喃乳糖带来了选择性增强，特别是对于混合型伽星素-3。增加价态在区分同源二聚体蛋白方面表现出作用，而将价态与头基延伸结合则导致对鸡伽星素的串联重复型伽星素-8的区分，但对人类伽星素-3和-4则没有影响。因此，详细的糖簇结构-活性谱分析结合适当地调节目标凝集素的接触位点，将有助于最小化这一类密切相关蛋白之间的交叉反应性。
• A General Chemoenzymatic Strategy for the Synthesis of Glycosphingolipids
  作者：Yunpeng Liu、Liuqing Wen、Lei Li、Madhusudhan Reddy Gadi、Wanyi Guan、Kenneth Huang、Zhongying Xiao、Mohui Wei、Cheng Ma、Qing Zhang、Hai Yu、Xi Chen、Peng George Wang、Junqiang Fang

  DOI：10.1002/ejoc.201600950

  日期：2016.9

  A concise, prototypical, and stereoselective strategy for the synthesis of therapeutically and immunologically significant glycosphingolipids has been developed. This strategy provides a universal platform for glycosphingolipid synthesis by block coupling of enzymatically prepared free oligosaccharideglycans to lipids using glycosyl N-phenyltrifluoroacetimidates as efficient activated intermediates

  已经开发了一种用于合成具有治疗和免疫学意义的鞘糖脂的简洁、原型和立体选择性策略。该策略通过使用糖基 N-苯基三氟乙酰亚胺酯作为有效活化中间体，将酶促制备的游离寡糖聚糖与脂质阻断偶联，为鞘糖脂合成提供了通用平台。如此处所示，使用该方法以优异的产率获得了两种不同类型的鞘糖脂。
• METHOD FOR THE SYNTHESIS OF A TRISACCHARIDE
  申请人：Dékany Gyula

  公开号：US20130131334A1

  公开（公告）日：2013-05-23

  The present invention relates to an improved synthesis of a trisaccharide of the formula (1), novel intermediates used in the synthesis and the preparation of the intermediates.

  本发明涉及一种改进的合成方法，用于合成式（1）的三糖，以及在合成过程中使用的新型中间体和中间体的制备。