β-lactosyl fluoride | 149342-82-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-lactosyl fluoride
• 英文别名: beta-Lactosyl fluoride；(2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-6-fluoro-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 149342-82-5
• 化学式: C₁₂H₂₁FO₁₀
• 分子量: 344.291
• InChiKey: MPJMJSVSVMGORJ-DCSYEGIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.7
• 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：
  169
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  β-lactosyl fluoride 在 endo-glucanase III 作用下， 以 acetate buffer 为溶剂， 生成 Lactose
  参考文献：
  名称：

  Colorimetric Assay for Evaluating Glycosyl Fluoride-hydrolyzing Activity of Glycosidase by Using Alizarin Complexon Reagent

  摘要：

  利用糖基氟化物开发了一种用于筛选糖苷酶的新型酶测定法。该方法基于氟离子与镧-茜素络合物（La3+-ALC）形成的络合物所引起的颜色变化。与使用对硝基苯糖苷作为筛选底物的传统方法相比，该检测方法显示出更高的灵敏度。对纯化纤维素酶催化的 β-内酰氟水解过程进行了定量研究，表明该方法也可用于酶动力学研究。

  DOI：

  10.1246/cl.2007.16
• 作为产物：
  描述：

  Gal2Ac3Ac4Ac6Ac(b1-4)Glc1F2Ac3Ac6Ac 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 β-lactosyl fluoride
  参考文献：
  名称：

  The role of hydrolases in a synthesis of some epoxyalkyl β-C-cellobiosides

  摘要：

  An endoglucanase from Humicola insolens has been used to glycosylate a range of alkenyl beta-D-C-glucopyranosides with beta-lactosyl fluoride. The resulting trisaccharides have been subjected to the action of a commercial beta-galactosidase to form alkenyl beta-C-cellobiosides. Oxidation of these has given a range of epoxyalkyl beta-C-cellobiosides, putative inhibitors of cellobiohydrolases. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01177-6

文献信息

• Cellulase-catalysed, stereoselective synthesis of oligosaccharides
  作者：Shin-Ichiro Shoda、Kei Obata、Olaf Karthaus、Shiro Kobayashi

  DOI：10.1039/c39930001402

  日期：——

  Oligosaccharides are synthesised enzymatically using β-lactosyl fluoride as glycosyl donor and a variety of mono-, di-and tri-saccharides as acceptors; the nature of the active site of the catalyst cellulase is discussed on the basis of these reactions.

  低聚糖通过酶法合成，以β-乳糖基氟化物为糖基供体，多种单糖、二糖和三糖作为受体；根据这些反应，探讨了催化剂纤维素酶活性中心的性质。
• One-Pot Enzymatic Synthesis and Biological Evaluation of Ganglioside GM3 Derivatives as Potential Cancer Immunotherapeutics
  作者：Juntao Wang、Dan Lu、Ran Sun、Shuwen Lei、Shuhua Luo、Xin Dang、Yang Zhang、Chang Yuan、Yong Zhang、Jinhong Wu、Guangyu Yang、Lei Fu、Faqin Jiang

  DOI：10.1021/acs.jmedchem.1c01301

  日期：2022.2.10

  worldwide. Recent research studies have revealed that GM3 derivatives have considerable promise as potential therapeutic agents for cancer. To discover novel GM3 derivatives as potential antitumor agents, a one-pot enzymatic synthesis was established, yielding 14 GM3 derivatives in high total yields (22–41%). Subsequently, the inhibitory activities of GM3 derivatives were assessed by wound-healing assays

  癌症是全世界死亡的主要原因。最近的研究表明，GM3 衍生物作为潜在的癌症治疗剂具有广阔的前景。为了发现新型 GM3 衍生物作为潜在的抗肿瘤药物，建立了一锅酶法合成方法，以高总产率 (22-41%) 产生了 14 种 GM3 衍生物。随后，通过伤口愈合试验和Transwell试验以及荷瘤动物模型评估了GM3衍生物的抑制活性。在所有GM3衍生物中， N-12在细胞中表现出优异的迁移和侵袭抑制作用，并且在C57BL/6小鼠中具有显着的抗肿瘤活性。随后对癌症组织和血清样本的分析表明， N-12可诱导肿瘤抑制，这与免疫反应密切相关。总而言之， N-12可以进一步开发为治疗癌症的有效疗法。然后进行 RNA 测序 (RNA-seq) 分析，结果表明N-12的抗肿瘤机制涉及粘着斑和 ECM-受体相互作用信号通路。
• Karthaus, Olaf; Shoda, Shin-ichiro; Takano, Hiroshi, Journal of the Chemical Society. Perkin transactions I, 1994, # 13, p. 1851 - 1858
  作者：Karthaus, Olaf、Shoda, Shin-ichiro、Takano, Hiroshi、Obata, Kei、Kobayashi, Shiro

  DOI：——

  日期：——
• Transglycosylation reactions with a crude culture filtrate from Thermoascusaurantiacus
  作者：Jörg Ortner、Martin Albert、Katherine Terler、Walter Steiner、Karl Dax

  DOI：10.1016/s0008-6215(00)00061-6

  日期：2000.8

  Some characteristics of regioselectivity and acceptor tolerance in transglycosylation reactions, catalysed by a crude culture filtrate from Thermoascus aurantiacus, were examined by employing methanol and monosaccharides as accepters. When beta-D-mannopyranosyl fluoride was employed as the donor, the anomeric configuration of the newly formed bond was found to depend on the structure of the acceptor used. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Novel method for polysaccharide synthesis using an enzyme: the first in vitro synthesis of cellulose via a nonbiosynthetic path utilizing cellulase as catalyst
  作者：Shiro Kobayashi、Keita Kashiwa、Tatsuya Kawasaki、Shinichiro Shoda

  DOI：10.1021/ja00008a042

  日期：1991.4

  The in vitro synthesis of cellulose via a nonbiosynthetic path has been achieved for the first time by condensation of beta-D-cellobiosyl fluoride as substrate for cellulase, a hydrolysis enzyme of cellulose, in a mixed solvent of acetonitrile/acetate buffer (pH 5, 5:1). The water-insoluble part of the products is ''synthetic cellulose'', the structure of which was confirmed by comparison with an authentic natural cellulose sample with use of solid C-13 NMR and IR spectroscopies as well as with a hydrolysis experiment. The present synthetic cellulose was converted to the corresponding triacetate whose molecular weight was at least 6.3 X 10(3) (degree of polymerization (DP) greater-than-or-equal-to 22). X-ray as well as C-13 NMR analyses showed that its crystal structure is of type II with high crystallinity. Under reaction conditions of a higher substrate concentration or higher acetonitrile concentration, water-soluble cellooligosaccharides (DP less-than-or-equal-to 8) were produced predominantly.