Polymer Institute, Slovak Academy of Sciences, Dúbravská cesta 9, 84541 Bratislava, Slovakia.
"Petru Poni" Institute of Macromolecular Chemistry, Grigore Ghica Voda 41A, 700487 Iasi, Romania.
Molecules. 2018 Sep 5;23(9):2259. doi: 10.3390/molecules23092259.
Cyclodextrins (CDs) were used in the present study for the ring-opening oligomerization (ROO) of l-lactide (LA) in order to synthesize biodegradable products with possible applications in pharmaceutical and medical fields. The practical importance of ROO reactions may reside in the possibility of synthesizing novel CD derivatives with high purity due to the dual role played by CDs, the role of the initiator through the hydroxylic groups, and the role of the catalyst by monomer inclusion in the CD cavity. The analyzed compounds were CDs modified with oligolactides obtained through ROO reactions of l-lactide in dimethylformamide. The resulting CD isomeric mixtures were investigated using classical characterization techniques such as gel permeation chromatography and nuclear magnetic resonance. Moreover, advanced mass spectrometry (MS) techniques were employed for the determination of the average number of monomer units attached to the cyclodextrin and the architecture of the derivatives (if the monomer units were attached as a single chain or as multiple chains). Thus, fragmentation studies effectuated on two different instruments (ESI Q-TOF and MALDI TOF) allowed us to correlate the size of the oligolactide chains attached to the CD with the observed fragmentation patterns.
在本研究中，环糊精（CDs）用于 L-丙交酯（LA）的开环聚合（ROO），以合成具有在制药和医疗领域可能应用的可生物降解产物。ROO 反应的实际重要性可能在于由于 CDs 的双重作用（通过羟基充当引发剂，通过单体包含在 CD 腔内充当催化剂），可以合成高纯度的新型 CD 衍生物。分析的化合物是通过在二甲基甲酰胺中进行 L-丙交酯的 ROO 反应获得的寡丙交酯修饰的 CD。使用凝胶渗透色谱和核磁共振等经典表征技术研究了所得 CD 异构体混合物。此外，还采用先进的质谱（MS）技术来确定连接到环糊精上的单体单元的平均数量和衍生物的结构（如果单体单元作为单链或多链连接）。因此，在两种不同的仪器（ESI Q-TOF 和 MALDI TOF）上进行的碎裂研究使我们能够将连接到 CD 上的寡丙交酯链的大小与观察到的碎裂模式相关联。
