Dipartimento di Chimica G. Ciamician, Alma Mater Studiorum Università di Bologna, Via Selmi 2, 40126 Bologna, Italy.
Amino Acids. 2011 Aug;41(3):609-20. doi: 10.1007/s00726-011-0908-0. Epub 2011 Apr 13.
A small library of stereoisomeric pseudopeptides able to make gels in different solvents has been prepared and their attitude to make gels in the presence of several metal ions was evaluated. Four benzyl esters and four carboxylic acids, all containing a moiety of azelaic acid (a long chain dicarboxylic acid) coupled with four different pseudopeptide moieties sharing the same skeleton (a phenyl group one atom apart from the oxazolidin-2-one carboxylic group), were synthesized in solution, by standard coupling reaction. The tendency of these pseudopeptides to form gels was evaluated using the inversion test of 10 mM solutions of pure compounds and of stoichiometric mixtures of pseudopeptides and metal ions. To obtain additional information on the molecular association, the gel samples were left dry in the air to form xerogels that were further analyzed using SEM and XRD. The formation of gel containing Zn(II) or Cu(II) ions gave good results in term of incorporation of the metal ions, while the presence of Cu(I), Al(III) and Mg(II) gave less satisfactory results. This outcome is a first insight in the formation of stable LMWGs formed by stoichiometric mixtures of pseudopeptides and metal ions. Further studies will be carried out to develop similar compounds of pharmacological interest.
已制备了能够在不同溶剂中形成凝胶的立体异构假肽的小库，并评估了它们在存在几种金属离子时形成凝胶的情况。通过标准偶联反应，在溶液中合成了四个苄酯和四个羧酸，它们都含有己二酸（长链二羧酸）的部分，与四个具有相同骨架（与噁唑烷-2-酮羧酸相隔一个原子的苯基）的不同假肽部分偶联。使用纯化合物和假肽与金属离子的化学计量混合物的 10 mM 溶液的倒置测试评估了这些假肽形成凝胶的趋势。为了获得有关分子缔合的更多信息，将凝胶样品在空气中干燥以形成干凝胶，然后使用 SEM 和 XRD 进一步分析。含有 Zn(II)或 Cu(II)离子的凝胶的形成在金属离子的掺入方面取得了良好的效果，而 Cu(I)、Al(III)和 Mg(II)的存在则效果较差。这一结果是通过假肽和金属离子的化学计量混合物形成稳定的低分子量凝胶的首次深入了解。将进一步开展研究以开发具有药理学意义的类似化合物。
