首页> 外文会议>Biorefinery I: Chemicals and materials from thermo-chemical biomass conversion and related processes >UPGRADED PRODUCTION OF A HYDROXYLACTONE ANHYDRO-SUGAR BY CELLULOSE PYROLYSIS AND ITS APPLICATION IN THE SYNTHESIS OF BIOLOGICALLY ACTIVE COMPOUNDS
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UPGRADED PRODUCTION OF A HYDROXYLACTONE ANHYDRO-SUGAR BY CELLULOSE PYROLYSIS AND ITS APPLICATION IN THE SYNTHESIS OF BIOLOGICALLY ACTIVE COMPOUNDS

机译:纤维素热裂解法生产羟乙基无水糖及其在生物活性化合物合成中的应用

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The fairly ignored (1R,5S)-anhydroisosaccharino-δ-lactone (LAC) is a compound formed at significant levels from catalytic pyrolysis of cellulose and lignocellulosic biomass. Recently LAC production in a gram scale by cellulose pyrolysis was upgraded. Isolation and purification procedures were improved and its presence in bio-oils quantitatively evaluated by a fast and efficient FT-IR method, previously validated by ~1HNMR analysis. The best results were obtained at 500 ℃ by mesoporous Sn-MCM-41 catalyst (7.6 % yield from cellulose, 6.6 % after a regeneration cycle) and by the cheap and eco-friendly montmorillonite K10 (4.8 %). LAC has the potential to be a top building block in biorefinery, being a multifunctional chiral C6 molecule. In this study we demonstrate that LAC is a valuable reagent in the synthesis of enantiomerically pure molecules with potential biological activities. Our first work employing LAC is given by the synthesis of a new tetrahydrofurane δ-amino acid, interesting as an equivalent of glycine-alanine dipeptide for access to new peptidomimetics with conformationally restricted structures. We also recognized structural similarity of this amino acid with natural L(+)-muscarine. Based on a renewed interest in muscarine-like conmpounds for application to the treatment of Alzheimer's disease and other cognitive disorders, we have used LAC for obtaining new muscarine analogues. They have been investigated with respect to their binding affinity to human muscarinic receptors, observing a good agreement of these data with results by docking calculations. Another application of LAC is given by the synthesis of a series of potentially antiviral compounds, related to nucleoside drugs.
机译:忽略不计的(1R,5S)-脱水异糖基-δ-内酯(LAC)是由纤维素和木质纤维素生物质的催化热解以显着水平形成的化合物。最近,通过纤维素热解以克为单位的LAC生产进行了升级。分离和纯化程序得到改进,并通过快速高效的FT-IR方法定量评估了其在生物油中的存在,该方法先前已通过〜1HNMR分析得到验证。最好的结果是在500℃下通过中孔Sn-MCM-41催化剂(纤维素的产率为7.6%,再生循环后为6.6%)和廉价且环保的蒙脱石K10(4.8%)获得的。 LAC作为多功能手性C6分子,有可能成为生物炼制中的重要基石。在这项研究中,我们证明了LAC是合成具有潜在生物活性的对映体纯分子的有价值的试剂。我们使用LAC的第一项工作是合成新的四氢呋喃δ-氨基酸,该氨基酸有趣地相当于甘氨酸-丙氨酸二肽的等效物,可用于接触具有构象受限结构的新型拟肽。我们还认识到该氨基酸与天然L(+)-毒蕈碱的结构相似性。基于对用于治疗阿尔茨海默氏病和其他认知障碍的毒蕈碱样化合物的新兴趣,我们已使用LAC来获得新的毒蕈碱类似物。已经对它们与人毒蕈碱受体的结合亲和力进行了研究,并通过对接计算观察到这些数据与结果具有很好的一致性。 LAC的另一种应用是合成一系列与核苷类药物有关的潜在抗病毒化合物。

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