1-thioglucose | 22566-82-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-thioglucose
• 英文别名: 1-deoxy-1-thio-D-glucopyranose；thioglucose；glucose；D-1-thio-glucose；1-thio-D-glucoside；1-thioglucoside；thioglucoside；Glucothiose；(2R,3S,4S,5R)-2-(hydroxymethyl)-6-sulfanyloxane-3,4,5-triol
• CAS: 22566-82-1
• 化学式: C₆H₁₂O₅S
• 分子量: 196.224
• InChiKey: JUSMHIGDXPKSID-GASJEMHNSA-N

物化性质

• 沸点：
  432.6±45.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  91.2
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-thioglucose 、 3-((5-bromopyridin-2-yl)oxy)-5,5-dimethyl-4-(4-(methylsulfonyl)phenyl)furan-2(5H)-one 在 diisopropylammonium bis(catecholato)isobutylsilicate 、 tetraaqua[4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]nickel(II) chloride 、 [Ru(bpy)₃](PF₆)₂ 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Ni /光氧化还原催化下未保护的肽和生物分子的可扩展硫代芳基化作用†

  摘要：

  未受保护的天然肽和生物分子的位点特异性功能化在合成设计和化学生物学中仍然是有用的转变，但是直到最近，有机合成中普遍使用的过渡金属催化方法的进步在应用于大型结构上时相对无效。复杂的生物分子。在这里，机理上独特的，未保护的天然硫醇（例如，Ni /光氧化还原催化的芳基化反应）（半胱氨酸残基）的报道–通过在环境条件下可见光促进的氢原子转移（HAT）事件启动的过程。采用双催化剂系统的亚化学计量负载（≤5mol％），具有出色的位点特异性，广泛的底物范围和较低的化学废料。通过适度的试剂调整，可以实现反应的可扩展性（从微克到克），并且高通量实验（HTE）证明了反应设置的简便性，从而可以快速筛选芳基卤化物偶联物和条件。硫醇底物和芳基实体的分数进行了检查，并有效地共轭，表明进一步多样化的实际应用。

  DOI：

  10.1039/c7sc04292b
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-1-thio-D-glucopyranose 在 甲醇 、 sodium methylate 作用下， 生成 1-thioglucose
  参考文献：
  名称：

  Versatile Functionalization of Polylysine:  Synthesis, Characterization, and Use of Neoglycoconjugates

  摘要：

  Glycopolymers are useful macromolecules with a non-carbohydrate backbone for presenting saccharides in a multivalent form. Here, a new methodology is described which allows easy access to water-soluble, biodegradable glycopolymers with both predeterminable composition and molecular weight distribution. Thus, chloroacetylation of commercially available polylysine hydrobromide 3 gave the reactive homopolymer 4, whose chloroacetamide functions allowed subsequent coupling with thiol-containing components. Water-soluble homopolymers such as 8 and 13 were available by treatment with an excess of hydrophilic thiols. Heteroglycopolymers were obtained via quantitative incorporation of substoichiometric amounts of carbohydrates with a mercapto functionality linked to the reducing end; the remaining chloroacetamide groups were capped with an excess of thioglycerol. A variety of glycopolymers with up to four different components was prepared. The composition and purity of the products were reliably analyzed by H-1 NMR. Generally, the quantitative incorporation of substoichiometric components was verified. The polymer backbone was not altered under the applied reaction conditions, as indicated by very similar polydispersities and degrees of polymerization of starting polylysine 3 and functionalized homo- and heteropolymers 8, 13, and 14. Glycopolymer 25, containing sialyl Lewis(a) and biotin as a functional group for enzyme linked immune sorbent assay, was used for developing cell-free selectin ligand binding assays. The inhibition of E-selectin by glycopolymers 1.6, containing sialyl Lewis(x) (sLe(x)), was evaluated in a cell adhesion assay under flow conditions using activated human umbilical vein endothelial cells and polymorphonuclear neutrophils. The sLe(x) polymers 16 showed no significant inhibition, whereas conjugates with additional charged groups (carboxylates 18, sulfonates 21) in addition to sLe(x) gave 30-35% reduction of the number of interacting cells at the same concentration of 100 mu M sLe(x).

  DOI：

  10.1021/ja984183p

文献信息

• Protein and peptide-free synthetic vaccines against streptococcus pneumoniae type 3
  申请人：Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.

  公开号：EP2851092A1

  公开（公告）日：2015-03-25

  The present invention provides a protein- and peptide-free conjugate comprising a synthetic carbohydrate and a carrier molecule, wherein the synthetic carbohydrate is a Streptococcus pneumoniae type 3 capsular polysaccharide related carbohydrate and the carrier molecule is a glycosphingolipid. Said conjugate and pharmaceutical composition thereof are useful for immunization against diseases associated with Streptococcus pneumoniae, and more specifically against diseases associated with Streptococcus pneumoniae type 3.

  本发明提供了一种不含蛋白质和多肽的缀合物，该缀合物包括一种合成碳水化合物和一个载体分子，其中合成碳水化合物是与肺炎链球菌3型荚膜多糖相关的碳水化合物，载体分子是一种糖鞘脂。所述缀合物及其药物组合物可用于免疫预防与肺炎链球菌相关的疾病，特别是与肺炎链球菌3型相关的疾病。
• [EN] PROTEIN AND PEPTIDE-FREE SYNTHETIC VACCINES AGAINST STREPTOCOCCUS PNEUMONIAE TYPE 3<br/>[FR] VACCINS SYNTHÉTIQUES SANS PROTÉINE ET SANS PEPTIDE CONTRE LE STREPTOCOCCUS PNEUMONIAE DE TYPE 3
  申请人：MAX PLANCK GES ZUR FÖRDERUNG DER WISSENSCHAFTEN E V

  公开号：WO2015040140A1

  公开（公告）日：2015-03-26

  The present invention provides a protein- and peptide-free conjugate comprising a synthetic carbohydrate and a carrier molecule, wherein the synthetic carbohydrate is a Streptococcus pneumoniae type 3 capsular polysaccharide related carbohydrate and the carrier molecule is a glycosphingolipid. Said conjugate and pharmaceutical composition thereof are useful for immunization against diseases associated with Streptococcus pneumoniae, and more specifically against diseases associated with Streptococcus pneumoniae type 3.

  本发明提供了一种不含蛋白质和多肽的缀合物，该缀合物包括一种合成碳水化合物和一个载体分子，其中合成碳水化合物是与肺炎链球菌3型荚膜多糖相关的碳水化合物，载体分子是一种糖鞘脂。所述缀合物及其药物组合物可用于免疫预防与肺炎链球菌相关的疾病，特别是与肺炎链球菌3型相关的疾病。
• [EN] QUINOLIN-4-ONE AND 4(1H)-CINNOLINONE COMPOUNDS AND METHODS OF USING SAME<br/>[FR] COMPOSÉS DE QUINOLIN-4-ONE ET DE 4(1H)-CINNOLINONE ET PROCÉDÉS D'UTILISATION ASSOCIÉS
  申请人：FREQUENCY THERAPEUTICS INC

  公开号：WO2020163816A1

  公开（公告）日：2020-08-13

  The present disclosure relates to quinolin-4-one and 4(1H)-cinnolinone compounds and methods of using them to induce self-renewal of stem/progenitor supporting cells, including inducing the stem/progenitor cells to proliferate while maintaining, in the daughter cells, the capacity to differentiate into tissue cells.

  本公开涉及喹啉-4-酮和4(1H)-喹啉酮化合物，以及使用它们诱导干/祖细胞支持细胞自我更新的方法，包括诱导干/祖细胞增殖，同时在子细胞中保持分化为组织细胞的能力。
• [EN] PEPTIDOMIMETICS FOR THE TREATMENT OF NOROVIRUS INFECTION<br/>[FR] PEPTIDOMIMÉTIQUES POUR LE TRAITEMENT D'UNE INFECTION À NOROVIRUS
  申请人：UNIV EMORY

  公开号：WO2017197377A1

  公开（公告）日：2017-11-16

  The present invention is directed to compounds, compositions and methods for preventing, treating or curing Norovirus infection in human subjects or other animal hosts.

  本发明涉及用于预防、治疗或治愈人类主体或其他动物宿主中的诺如病毒感染的化合物、组合物和方法。
• [EN] OLIGOSACCHARIDES AND OLIGOSACCHARIDE-PROTEIN CONJUGATES DERIVED FROM CLOSTRIDIUM DIFFICILE POLYSACCARIDE PS-I, METHODS OF SYNTHESIS AND USES THEREOF, IN PARTICULAR AS VACCINES AND DIAGNOSTIC TOOLS<br/>[FR] OLIGOSACCHARIDES ET CONJUGUÉS D'OLIGOSACCHARIDES-PROTÉINES PROVENANT DE POLYSACCARIDES PS-I DE CLOSTRIDIUM DIFFICILE, LEURS PROCÉDÉS DE SYNTHÈSE ET D'UTILISATION, EN PARTICULIER EN TANT QUE VACCINS ET OUTILS DE DIAGNOSTIC
  申请人：MAX PLANCK GESELLSCHAFT

  公开号：WO2013017254A1

  公开（公告）日：2013-02-07

  The invention relates to a synthetic oligosaccharide representing part of the repeating unit of the Clostridium difficile glycopolymer PS-I and having the sequence of the pentasaccharide a-L-Rhap- ( 1→3 ) -β-D-Glcp- ( 1→4 ) - [a-L-Rhap- ( 1→3 ] -a-D-Glcp- ( 1→2 ) -a-D-Glcp or a synthetic fragment or derivative thereof. Preferably, the claimed synthetic oligosaccharide bears at least one linker L for conjugation to a carrier protein or for immobilization on a surface. Further aspects of the invention relate to advantageous methods for synthesizing said synthetic oligosaccharide and oligosaccharide-protein conjugate as well as to uses thereof, in particular as vaccines and diagnostic tools.

  该发明涉及一种合成的寡糖，代表Clostridium difficile糖聚合物PS-I的重复单元的一部分，并具有五糖基序列a-L-Rhap-（1→3）-β-D-Glcp-（1→4）-[a-L-Rhap-（1→3]-a-D-Glcp-（1→2）-a-D-Glcp或其合成片段或衍生物。优选，所述的合成寡糖至少带有一个连接子L，用于与载体蛋白共轭或固定在表面上。该发明的进一步方面涉及有利的合成所述合成寡糖和寡糖-蛋白共轭的方法，以及它们的用途，特别是作为疫苗和诊断工具。