生物素-六聚乙二醇-五氟苯酚酯 | 1352814-12-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 中文名称: 生物素-六聚乙二醇-五氟苯酚酯
• 英文名称: Biotin-PEG6-PFP ester
• 英文别名: (2,3,4,5,6-pentafluorophenyl) 3-[2-[2-[2-[2-[2-[2-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]propanoate
• CAS: 1352814-12-0
• 化学式: C₃₁H₄₄F₅N₃O₁₀S
• 分子量: 745.762
• InChiKey: GXLWAKRKYSWKJQ-WURXVLGASA-N

物化性质

• 沸点：
  843.7±65.0 °C(Predicted)
• 密度：
  1.293±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  50
• 可旋转键数：
  28
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  177
• 氢给体数：
  3
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  生物素-六聚乙二醇-五氟苯酚酯 、 3-aminopropyl 3-O-(methylphosphonato)-α-D-mannopyranosyl-(1→2)-α-D-mannopyranoside 在 三乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以40 %的产率得到
  参考文献：
  名称：

  与肺炎克雷伯菌 O3 血清型脂多糖 O 抗原结构相关的甲基磷酸化寡甘露糖苷的合成及其在兔和人血清中特异性抗体检测中的应用

  摘要：

  合成了与 O3 血清型肺炎克雷伯菌的脂多糖 (LPS) O 抗原结构相关的甲基磷酸化单甘露糖苷、二甘露糖苷和三甘露糖苷，并与生物素标签缀合。使用均匀的单糖合成嵌段进行目标碳水化合物链的立体和区域选择性组装。之后，通过与甲基-H-膦酸酯试剂偶联引入甲基磷酸基团，然后氧化和脱保护，得到目标寡糖。所得化合物的1 H 和13 C NMR谱与相应天然多糖的谱图吻合良好。新制备的生物素化寡糖以及先前报道的与肺炎克雷伯菌LPS的半乳聚糖I和半乳聚糖II相关的生物素化糖缀合物用于ELISA检测抗肺炎克雷伯菌兔血清中的抗体。抗O3血清抗体特异性识别具有末端甲基磷酸甘露糖基残基的合成寡糖配体，而抗O1血清抗体识别与肺炎克雷伯菌半乳聚糖II相关的寡糖。对确诊克雷伯氏菌感染患者的人体血清分析也表明，临床病例中存在针对合成寡糖的抗体。因此，所描述的化合物与其他克雷伯氏菌相关的抗原寡糖一起可以潜在地用作肺炎克雷伯氏菌

  DOI：

  10.1039/d3ob01203d
• 作为产物：
  描述：

  六甘醇 在 吡啶 、 sodium azide 、 氢气 、 sodium hydride 、 三乙胺 、 乙酰氯 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 166.0h， 生成 生物素-六聚乙二醇-五氟苯酚酯
  参考文献：
  名称：

  Synthesis and Molecular Recognition Studies of the HNK-1 Trisaccharide and Related Oligosaccharides. The Specificity of Monoclonal Anti-HNK-1 Antibodies as Assessed by Surface Plasmon Resonance and STD NMR

  摘要：

  The human natural killer cell carbohydrate, HNK-1, plays function-conducive roles in peripheral nerve regeneration and synaptic plasticity. It is also the target of autoantibodies in polyneuropathies. It is thus important to synthesize structurally related HNK-1 carbohydrates for optimizing its function-conducive roles, and for diagnosis and neutralization of autoantibodies in the fatal Guillain-Barre syndrome. As a first step toward these goals, we have synthesized several HNK-1 carbohydrate derivatives to assess the specificity of monoclonal HNK-1 antibodies from rodents: 2-aminoethyl glycosides of selectively O-sulfated trisaccharide corresponding to the HNK-1 antigen, its nonsulfated analogue, and modified structures containing 3-O-fucosyl or 6-O-sulfo substituents in the N-acetylglucosamine residues. These were converted, together with several related oligosaccharides, into biotin-tagged probes to analyze the precise carbohydrate specificity of two anti-HNK-1 antibodies by surface plasmon resonance that revealed a crucial role of the glucuronic acid in antibody binding. The contribution of the different oligosaccharide moieties in the interaction was shown by saturation transfer difference (STD) NMR of the complex consisting of the HNK-1 pentasaccharide and the HNK-1 412 antibody.

  DOI：

  10.1021/ja2083015

文献信息

• Synthesis of 3-aminopropyl β-(1 → 6)-d-glucotetraoside and its biotinylated derivative
  作者：Dmitry V. Yashunsky、Alexander A. Karelin、Yury E. Tsvetkov、Nikolay E. Nifantiev

  DOI：10.1016/j.carres.2017.11.001

  日期：2018.1

  3-Aminopropyl β-(1 → 6)-d-glucotetraoside has been synthesized from 3-benzyloxycarbonylaminopropanol and 6-O-acetyl-2,3,4-tri-O-benzoyl-d-glucopyranosyl trichloroacetimidate by successive attachment of one monosaccharide unit in total yield of 22%. Free aminopropyl glycoside was converted into a biotin derivative that can be used for controlled immobilization of the oligosaccharide on streptavidin-coated

  由3-苄氧基羰基氨基丙醇和6-O-乙酰基-2,3,4-三-O-苯甲酰基-d-吡喃葡萄糖基三氯乙亚氨酸酯合成3-氨基丙基β-（1→6）-d-葡萄糖四糖苷总产量的22％。游离的氨基丙基糖苷被转化为生物素衍生物，可用于寡糖在链霉亲和素包被的ELISA板上的可控固定和追踪碳水化合物结合分子。
• Synthesis of a biotinylated probe from biotechnologically derived β-d-mannopyranosyl-(1 → 2)-d-mannopyranose for assessment of carbohydrate specificity of antibodies
  作者：Alexander A. Karelin、Nadezhda E. Ustyuzhanina、Yury E. Tsvetkov、Nikolay E. Nifantiev

  DOI：10.1016/j.carres.2018.10.013

  日期：2019.1

  The disaccharide β-d-mannopyranosyl-(1 → 2)-d-mannopyranose obtained by chemical cleavage and enzymatic dephosphorylation of biotechnologically available phosphomannan was transformed over six steps into a biotinylated probe suitable for assessment of carbohydrate specificity of antibodies induced by yeast cell wall preparations.

  通过对生物技术上可利用的磷酸甘露聚糖进行化学裂解和酶促脱磷酸作用而获得的二糖β-d-甘露吡喃糖基-（1→2）-d-甘露吡喃糖经六步转化为生物素化探针，适用于评估酵母细胞壁诱导的抗体的碳水化合物特异性准备。
• Conditions of catalytic hydrogenolysis for the simultaneous reduction of azido group and debenzylation of chitooligosaccharides. Synthesis of biotinylated derivatives of chitooligosaccharides
  作者：O. N. Yudina、Yu. E. Tsvetkov、N. E. Nifantiev

  DOI：10.1007/s11172-016-1681-8

  日期：2016.12

  Hydrogenation over Pd(OH)2/C in a methanol—water—acetic acid mixture allows one to carry out the efficient simultaneous reduction of the azido group and remove the benzyl groups in 2-azidoethyl glycosides of benzylated chitooligosaccharides. The obtained 2-aminoethyl glycosides of free chitooligosaccharides were converted to the corresponding biotinylated conjugates serving as tools for glycobiological investigations.

  在甲醇-水-乙酸混合物中通过 Pd(OH)2/C 进行氢化，可以同时高效地还原叠氮基并去除苄基化壳寡糖 2-叠氮乙基糖苷中的苄基。获得的游离壳寡糖的 2-氨乙基糖苷被转化为相应的生物素化缀合物，作为糖生物学研究的工具。
• Synthesis of a Pentasaccharide and Neoglycoconjugates Related to Fungal α-(1→3)-Glucan and Their Use in the Generation of Antibodies to Trace<i>Aspergillus fumigatus</i>Cell Wall
  作者：Bozhena S. Komarova、Maria V. Orekhova、Yury E. Tsvetkov、Remi Beau、Vishukumar Aimanianda、Jean-Paul Latgé、Nikolay E. Nifantiev

  DOI：10.1002/chem.201404770

  日期：2015.1.12

  position and 3‐OH group, respectively. Their removal from shared blocks led to donors and acceptors that were used for the synthesis of pentasaccharides. Coupling of free α‐(1→3)‐pentaglucoside with biotin and bovine serum albumin (BSA) gave glycoconjugate tools for mycological studies. Immunization of mice with the BSA conjugate induced the generation of antibodies that recognize α‐(1→3)‐glucan on A

  烟曲霉细胞壁的α-（1→3）-葡聚糖片段3-氨基丙基α-（1→3）-五葡糖苷是通过块状方法合成的。带有立体定向6- O-苯甲酰基的单糖和二糖N-苯基三氟乙酰亚氨酸盐的应用对于立体选择性α-葡萄糖基化至关重要。在产品中，p‐甲氧基苯基和乙酰丙酰基分别用作异头位置和3-OH基团的正交保护基。它们从共有的嵌段中除去导致供体和受体被用于合成五糖。游离的α-（1→3）-五葡糖苷与生物素和牛血清白蛋白（BSA）的偶联为糖基结合物的真菌学研究提供了工具。用BSA偶联物免疫小鼠会诱导产生识别烟曲霉细胞壁上的α-（1→3）-葡聚糖的抗体，并区分其形态型。这一发现代表了诊断测试系统和疫苗的开发的第一步，该系统可以检测和抵抗这种威胁生命的病原体。
• The Synthesis of Blood Group Antigenic A Trisaccharide and Its Biotinylated Derivative
  作者：Ekaterina D. Kazakova、Dmitry V. Yashunsky、Nikolay E. Nifantiev

  DOI：10.3390/molecules26195887

  日期：——

  Blood group antigenic A trisaccharide represents the terminal residue of all A blood group antigens and plays a key role in blood cell recognition and blood group compatibility. Herein, we describe the synthesis of the spacered A trisaccharide by means of an assembly scheme that employs in its most complex step the recently proposed glycosyl donor of the 2-azido-2-deoxy-selenogalactoside type, bearing

  血型抗原A三糖代表所有A血型抗原的末端残基，在血细胞识别和血型相容性中起着关键作用。在此，我们描述了通过组装方案合成间隔A三糖，该组装方案在其最复杂的步骤中采用了最近提出的2-叠氮基-2-脱氧-硒代半乳糖苷类型的糖基供体，带有立体控制的3-O-苯甲酰基和4,6-O-(二叔丁基亚甲硅基)-保护基团。其应用提供了所需 α-糖基化产物的高效和立体选择性形成，然后将其去保护并进行间隔物生物素化以得到生化研究所需的两种目标产物。