2'-azidoethyl-2,3,4-tri-O-acetyl-α-D-mannopyranoside | 1207538-18-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-azidoethyl-2,3,4-tri-O-acetyl-α-D-mannopyranoside
• 英文别名: [(2R,3R,4S,5S,6S)-4,5-diacetyloxy-6-(2-azidoethoxy)-2-(hydroxymethyl)oxan-3-yl] acetate
• CAS: 1207538-18-8
• 化学式: C₁₄H₂₁N₃O₉
• 分子量: 375.335
• InChiKey: RSSXFXKLHHBWQT-DGTMBMJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  132
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2'-azidoethyl-2,3,4-tri-O-acetyl-α-D-mannopyranoside 在 10% palladium on activated charcoal 、 copper(II) bis(trifluoromethanesulfonate) 甲醇 、 氢气 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.66h， 生成 dimethyl (1S,2S,4S,5S)-4-(((2R,3S,4S,5S,6S)-6-(2-aminoethoxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)methoxy)-5-(((2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)cyclohexane-1,2-dicarboxylate
  参考文献：
  名称：

  Inhibitors of microbial infections

  摘要：

  本发明适用于医学领域，特别是涉及用于治疗和/或预防HIV，埃博拉，登革热，丙型肝炎，SARS或结核感染的新化合物。

  公开号：

  EP2289904A1
• 作为产物：
  描述：

  (2S,3S,4S,5S,6R)-2-(2-Azido-ethoxy)-6-trityloxymethyl-tetrahydro-pyran-3,4,5-triol 在 水 、 溶剂黄146 作用下， 生成 2'-azidoethyl-2,3,4-tri-O-acetyl-α-D-mannopyranoside
  参考文献：
  名称：

  ‘Click’ glycosylation of peptides through cysteine propargylation and CuAAC

  摘要：

  半胱氨酸肽通过Cu(I)催化的叠氮化物-炔烃环加成(CuAAC)实现了"点击"糖基化，产率良好。此方法中，肽通过半胱氨酸残基的直接炔基化进行官能化，使其可用于与具有gluco、manno和galacto构型的合适叠氮化糖（自由或保护状态）进行CuAAC反应。在所获得的自由和保护型糖肽中，一系列"glycoRGD"肽被制备并进行了体外血小板聚集测试，结果显示伪糖基化的黏附序列降低了IC50值，从而可能改善体内药代动力学特性。©2014 Elsevier Ltd. 保留所有权利。

  DOI：

  10.1016/j.bmc.2014.09.056

文献信息

• GLYCOSIDE DERIVATIVES, PREPARATION THEREOF AND USE THEREOF AS PROSTHETIC GROUPS
  申请人：UNIVERSITÉ DE LORRAINE

  公开号：US20160031923A1

  公开（公告）日：2016-02-04

  The present invention relates to glycoside-derived compounds, to the processes for preparing same and to the use thereof as prosthetic groups for radiolabelling biomolecules. These compounds are co-azido-alkyl 6-deoxy-6-[ 18 F]-fluoroglycosides of formula (I), in which: k is equal to 2 or 3; n is an integer between 1 and 5; R is independently H or a C 1 -C 5 alkyl group, m being an integer between 0 and 2 if k=2 and m between 0 and 3 if k=3; and X is chosen from the group comprising O, S, CH 2 and NR′, in which R′ is independently a C 1 -C 5 alkyl group or an aryl group, including all the stereoisomers thereof.

  本发明涉及糖苷衍生化合物，制备这些化合物的方法以及将其用作放射标记生物分子的假体基团。这些化合物是公式（I）的共氮烷基6-去氧-6-[18F]-氟糖苷，其中：k等于2或3；n是1到5之间的整数；R独立地是H或C1-C5烷基，如果k=2，则m是0到2之间的整数，如果k=3，则m是0到3之间的整数；X从包括O、S、CH2和NR′的群体中选择，其中R′独立地是C1-C5烷基或芳基，包括所有的立体异构体。
• Development of 6-[¹⁸F]fluoro-carbohydrate-based prosthetic groups and their conjugation to peptides via click chemistry
  作者：Charlotte Collet、Fatiha Maskali、Alexandra Clément、Françoise Chrétien、Sylvain Poussier、Gilles Karcher、Pierre-Yves Marie、Yves Chapleur、Sandrine Lamandé-Langle

  DOI：10.1002/jlcr.3362

  日期：2016.2

  This work describes the development of new 6-[18F]fluoro-carbohydrate-based prosthetic groups equipped with an azido arm that are able to participate in copper(I)-catalyzed cycloadditions for 18F labeling of biomolecules under mild conditions. The radiolabeling in high radiochemical yields (up to 68 ± 6%) of these different prosthetic groups is presented. The flexibility of the azido arm introduced on the carbohydrate moieties allows efficient click reactions with different alkyne functionalized peptides such as gluthation or Arg-Gly-Asp derivatives in order to prepare glycopeptides. The radiosyntheses of 18F-labeled glycopeptides proceed in high radiochemical yields (up to 76%) in an automated process with excellent radiochemical purity. The addition of a sugar moiety on peptides should enhance the bioavailability, pharmacokinetic, and in vivo clearance properties of these glycopeptides, compared with the unlabeled native peptide, and these properties are highly favorable for positron emission tomography imaging. A high uptake of 18F-β-gluco-c(RGDfC) is shown by positron emission tomography imaging in a subcutaneous abscess model in the rat, revealing the potential of this tracer to monitor integrin expression as a part of inflammation and/or angiogenesis processes.

  这项工作描述了新型6-[18F]氟代碳水化合物衍生辅基的开发，这些辅基配备了一个叠氮臂，能够在温和条件下参与铜(I)催化的环加成反应，用于生物分子18F标记。本文介绍了这些不同辅基的高放射化学产率（最高达68 ± 6%）的放射性标记。将叠氮臂引入到碳水化合物部分所提供的灵活性，使得其能与不同的炔基功能化肽（如谷胱甘肽或精氨酸-甘氨酸-天冬氨酸衍生物）高效进行点击反应，从而制备糖肽。18F标记糖肽的放射合成在自动化过程中以高放射化学产率（高达76%）进行，并且具有优异的放射性化学纯度。与未标记的天然肽相比，在肽上附加糖部分应改善这些糖肽的生物利用度、药代动力学和体内清除特性，这些特性对于正电子发射断层扫描成像非常有利。正电子发射断层扫描成像显示，18F-β-葡糖-c(RGDfC)在大鼠皮下脓肿模型中具有高摄取量，揭示了这种示踪剂在监测作为炎症和/或血管生成过程一部分的整合素表达方面的潜力。
• [EN] INHIBITORS OF MICROBIAL INFECTIONS<br/>[FR] INHIBITEURS D'INFECTIONS MICROBIENNES
  申请人：UNIV DEGLI STUDI MILANO

  公开号：WO2011000721A1

  公开（公告）日：2011-01-06

  The present invention finds application in the field of medicine and, in particular, it relates to new compounds for the treatment and/or prevention of HIV; Ebola, Dengue, Hepatitis C, SARS or tuberculosis infections.

  本发明适用于医学领域，特别是涉及用于治疗和/或预防HIV、埃博拉、登革热、丙型肝炎、SARS或结核感染的新化合物。
• Inhibition of DC-SIGN-Mediated HIV Infection by a Linear Trimannoside Mimic in a Tetravalent Presentation
  作者：Sara Sattin、Anna Daghetti、Michel Thépaut、Angela Berzi、Macarena Sánchez-Navarro、Georges Tabarani、Javier Rojo、Franck Fieschi、Mario Clerici、Anna Bernardi

  DOI：10.1021/cb900216e

  日期：2010.3.19

  HIV infection is pandemic in humans and is responsible for millions of deaths every year. The discovery of new cellular targets that can be used to prevent the infection process represents a new opportunity for developing more effective antiviral drugs. In this context, dendritic cell-specific ICAM-3 grabbing nonintegrin (DC-SIGN), a lectin expressed at the surface of immature dendritic cells and involved in the initial stages of HIV infection, is a promising therapeutic target. Herein we show the ability of a new tetravalent dendron containing four copies of a linear trimannoside mimic to inhibit the trans HIV infection process of CD4+ T lymphocytes at low micromolar range. This compound presents a high solubility in physiological media, a neglectable cytotoxicity, and a long-lasting effect and is based on carbohydrate-mimic units. Notably, the HIV antiviral activity is independent of viral tropism (X4 or R5). The formulation of this compound as a gel could allow its use as topical microbicide.
• DERIVES DE GLYCOSIDES, LEUR PREPARATION ET LEUR UTILISATION COMME GROUPES PROSTHETIQUES
  申请人：Université de Lorraine

  公开号：EP2867244A1

  公开（公告）日：2015-05-06