2-(tri-O-acetyl-α-L-fucopyranosyl)acetic acid | 167990-26-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(tri-O-acetyl-α-L-fucopyranosyl)acetic acid
• 英文别名: 2,3,4-O-acetyl-α-L-C-fucosyl carboxylic acid；2-(2,3,4-tri-O-acetyl-α-L-C-fucopyranosyl)acetic acid；2-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)acetic acid；2-[(2S,3R,4R,5R,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]acetic acid
• CAS: 167990-26-3
• 化学式: C₁₄H₂₀O₉
• 分子量: 332.307
• InChiKey: PYVYNZRWVIXFRI-XRYYQZTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5,11,17,23-tetra(glycylamido)-25,26,27,28-tetrapropoxycalix[4]arene tetrahydrochloride 、 2-(tri-O-acetyl-α-L-fucopyranosyl)acetic acid 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 以71%的产率得到5,11,17,23-tetrakis[2-(2,3,4-tri-O-acetyl-α-L-fucosyl)acetylglycylamido]-25,26,27,28-tetrapropoxycalix[4]arene
  参考文献：
  名称：

  Multivalent calixarene-based C-fucosyl derivative: a new Pseudomonas aeruginosa biofilm inhibitor

  摘要：

  The first example of multivalent conjugate in which four alpha-L-C-fucosyl units are clustered by means of a calix[4]arene platform was designed as a new potential Pseudomonas aeruginosa biofilm inhibitor. The anti-biofilm activity of the synthesized compound (6) against PAO1 strain was assayed and it was found to be dose-dependent. The presence of the fucose cluster improves the biofilm inhibitor efficiency as proven by the lower inhibitor activity of the analogous glycyl-calix[4]arene derivative (3) lacking in the fucose moieties. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.08.142
• 作为产物：
  描述：

  2-(tri-O-acetyl-α-L-fucopyranosyl)acetaldehyde 在 sodium chlorite 、 2-甲基-2-丁烯 、 Na₂H₂PO₄ 作用下， 以 水 、 叔丁醇 为溶剂， 生成 2-(tri-O-acetyl-α-L-fucopyranosyl)acetic acid
  参考文献：
  名称：

  Generation of C-Glycoside Peptide Ligands for Cell Surface Carbohydrate Receptors Using a Four-Component Condensation on Solid Support

  摘要：

  DOI：

  10.1021/jo960119j

文献信息

• Synthesis of a calix[4]arene derivative exposing multiple units of fucose and preliminary investigation as a potential broad-spectrum antibiofilm agent
  作者：Giuseppe Granata、Stefano Stracquadanio、Grazia Maria Letizia Consoli、Viviana Cafiso、Stefania Stefani、Corrada Geraci

  DOI：10.1016/j.carres.2019.03.005

  日期：2019.4

  Calix[4]arene derivative (1), bearing four α-l-C-fucosyl units linked via a flexible spacer, and a monomeric analogous (2) bearing a single moiety of fucose, were synthesized. Compounds 1 and 2 were assayed for antibiofilm activity against Pseudomonas aeruginosa (Gram-) and Staphylococcus epidermidis (Gram+). The macrocyclic compound 1 showed very high percentage of biofilm inhibition against two different

  合成了带有通过柔性间隔基连接的四个α-1C-岩藻糖基单元的杯[4]芳烃衍生物（1）和带有单个岩藻糖部分的单体类似物（2）。测定化合物1和2对铜绿假单胞菌（Gram-）和表皮葡萄球菌（Gram +）的抗生物膜活性。大环化合物1对两种不同细菌菌株显示出非常高的生物膜抑制率，而没有大环结构的化合物2对铜绿假单胞菌仅显示中度生物膜抑制，而对表皮葡萄球菌则无生物膜抑制。岩藻糖多价衍生物可能是一种新型的广谱抗生物膜剂。
• Combinatorial variation of branching length and multivalency in a large (390 625 member) glycopeptide dendrimer library: ligands for fucose-specific lectins
  作者：Emma M. V. Johansson、Elena Kolomiets、Frank Rosenau、Karl-Erich Jaeger、Tamis Darbre、Jean-Louis Reymond

  DOI：10.1039/b616051b

  日期：——

  A new approach to dendrimer property tuning is demonstrated by combinatorial variation of dendrimer branch length and multivalency level, using a large (390 625-member) self-encoded glycopeptide dendrimer library. Ligands for the fucose lectins of Ulex europaeus were identified by screening a combinatorial library of dendrimers with variable arm length (0–4 amino acids) and multivalency (2–5 end groups). The ligands identified by this approach also bind to the fucose lectin LecB (PA-IIL) of Pseudomonas aeruginosa, and might provide a possible starting point to develop anti-infective agents against this antibiotic resistant pathogen which causes lethal respiratory tract infections in cystic fibrosis patients.

  通过组合变化树状分子分支长度和多价水平，使用一个大型（390个成员）自编码糖肽树状分子库，展示了树状分子性质调整的新方法。通过筛选具有可变臂长（0-4个氨基酸）和多价（2-5个末端基团）的树状分子组合库，确定了欧洲荨麻的岩藻糖凝集素的配体。通过这种方法确定的配体还与铜绿假单胞菌的岩藻糖凝集素LecB（PA-IIL）结合，这可能是开发抗感染药物的起点，以对抗这种导致囊性纤维化患者致命呼吸道感染的抗生素耐药病原体。
• Neoglycopeptide Dendrimer Libraries as a Source of Lectin Binding Ligands
  作者：Elena Kolomiets、Emma M. V. Johansson、Olivier Renaudet、Tamis Darbre、Jean-Louis Reymond

  DOI：10.1021/ol070119d

  日期：2007.4.1

  A 15 625-membered peptide dendrimer combinatorial library was acylated with an alpha-C-fucosyl residue at its four N-termini and screened for binding to fucose-specific lectins. Dendrimer FD2 (Fuc-alpha-CH2CO-Lys-Pro-Leu)(4)(Lys-Phe-Lys-Ile)(2)Lys-His-Ile-NH2 was identified as a potent ligand against Ulex europaeus lectin UEA-I (IC50 = 11 mu M) and Pseudomonas aeruginosa lectin PA-IIL (IC50 = 0.14 mu M).
• SACCHAROPEPTIDES AND DERIVATIVES THEREOF
  申请人：GLYCOMED INCORPORATED

  公开号：EP0824538A1

  公开（公告）日：1998-02-25
• [EN] SACCHAROPEPTIDES AND DERIVATIVES THEREOF<br/>[FR] SACCHAROPEPTIDES ET DERIVES
  申请人：——

  公开号：WO1996035700A1

  公开（公告）日：1996-11-14

  [EN] The present invention describes glycomimetic saccharopeptides of formula (I): W-(X)n-Y-[(X)n-W-(X)n-Y]m-(X)n-W, wherein W is independently selected from the group consisting of a) saccharides; b) aryl, aralkyl; c) alkyl of 1 to 8 carbon atoms, optionally substituted; d) cyclic alkyl or 5-7 carbon atoms, heterocyclic alkyl. Y is independently selected from the group consisting of -NR<3>-C(O)- and -C(O)-NR<3>-; X is a difunctional or polyfunctional group selected from the group consisting of a) aryl, aralkyl; b) alkyl of 1-8 carbon atoms, optionally substituted with 1-3 substituents. R is -H, or lower alkyl, lower aryl, and lower aralkyl; R' is independently selected from the group consisting of -H, lower alkyl of 1-4 carbon atoms, aralkyl of 2 to 19 carbon atoms, and -C(O)R"; R" is lower alkyl of 1 to 4 carbon atoms; and R<3> is selected from the group consisting of -H, alkyl of 1-8 carbon atoms, and aralkyl of 5-8 carbon atoms; and pharmaceutically acceptable salts thereof.
  [FR] La présente invention concerne des saccharopeptides glycomimétiques représentés par la formule générale (I): W-(X)n-Y-[(X)n-W-(X)n-Y]m-(X)n-W ainsi que certains de ses sels pharmacologiquement admis. Dans cette formule, W est choisi indépendamment dans le groupe constitué a) des saccharides, b) des aryles et aralkyles, c) des alkyles portant 1 à 8 atomes de carbone, éventuellement substitués et d) des alkyles cycliques ou des alkyles hétérocycliques portant 5 à 7 atomes de carbones. Y est choisi indépendamment dans le groupe constitué des -NR<3>-C(O) et -C(O)-NR<3>-. X est un groupe bifonctionnel ou polyfonctionnel choisi dans le groupe constitué a) des aryles et aralkyles et b) des alkyles portant 1 à 8 atomes de carbone ayant éventuellement 1 à 3 substituants. R est -H ou alkyle inférieur, aryle inférieur et aralkyle inférieur. R' est choisi indépendamment dans le groupe constitué des -H, alkyles inférieurs portant 1 à 4 atomes de carbone, aralkyles portant de 2 à 19 atomes de carbone et de -C(O)R". R" est alkyle inférieur portant 1 à 4 atomes de carbone. Enfin, R<3> est choisi dans le groupe constitué des -H, alkyles portant 1 à 8 atomes de carbone et aralkyles portant 5 à 8 atomes de carbone.