Prolin bazlı kiral reseptörlerin sentezi

Abstract

Bu çalışmada cbz-S-prolin çeşitli aminlerle tepkimeye sokularak prolin bazlı kiral reseptörler (4, 5, 6 ve 7) elde edilmiştir. Benzer şekilde cbz-fenilglisin de üç farklı aminle tepkimeye sokularak fenilglisin bazlı kiral reseptörler olan 10, 11, 13, 14, 16 ve 17 nolu bileşikler elde edilmiştir. Sentezlenen fenilglisin bazlı kiral reseptörler cbz-S-prolin ile tepkimeye sokularak farklı kiral reseptörler (19, 21 ve 23) sentezlenmiştir. Ayrıca p-tet-bütilkaliks[4]arenin klorasetil klorür türevleriyle (24, 25 ve 26) reaksiyonu sonucu dört yeni kiral kaliks[4]aren amit türevleri (27, 28, 29 ve 30) sentezlenmiştir. 4, 5, 6 ve 7 nolu bileşiklerin rasemik karboksilik asitlerin enantiyomerlerine karşı kiral tanınma özellikleri 1H NMR spektroskopisi kullanılarak incelenmiştir. Bu bileşiklerin karboksilik asitlerin enantiyomerlerinin her birisi ile molar kesri ve birleşme sabitleri Job Plot ve en küçük kareler metodu kullanılarak belirlenmiştir.Gerçekleştirilen tüm reaksiyonlar İTK ile izlenmiş ve elde edilen ürünler kolon kromatografisi ile saflaştırılarak yapıları IR ve 1H NMR, 13C NMR ve elementel analiz teknikleriyle aydınlatıldıktan sonra kiral bileşiklerin optik çevirme açıları ölçülmüştür.

In this study, chiral receptors based proline (4, 5, 6 and 7) have been synthesized from the reaction of cbz-S-proline with amines. Similar to this reaction cbz-phenylglycine reacted with three different amines and chiral receptors based phenylglycine (10, 11, 13, 14, 16 and 17) have been synthesized from this reaction. Different chiral receptors based proline (19, 21 and 23) have been synthesized from the reaction of synthesized chiral receptors based phenylglycine with cbz-S-proline. In addition, four novel chiral amide derivatives of calix[4]arene (27, 28, 29 and 30) have been synthesized from the reaction of chloroacetyl chloride derivatives (24, 25 and 26) with p-tert-butylcalix[4]arene. Chiral recognition capability of 4, 5, 6 and 7 towards the enantiomers of racemic carboxylic asids, by 1H NMR spectroscopy was investigated. The molar ratio and the association constants of chiral compounds 4, 5, 6 and 7 with each of the enantiomers of carboxylic asids were determined by using Job plots and nonlinear least-squares fitting method, respectively.The reactions were monitored by TLC and pure compounds were obtained after crystallysation, column chromatography or both. The structures of synthesized compounds were identified by IR, 1H NMR 13C NMR, elemental analysis and optical rotation measurements were also included.