Journals / Iğdır Üniversitesi Fen Bilimleri Enstitüsü Dergisi / 2026 / Cilt: 11 Sayı: 2

Synthesis and Enantiomeric Recognition Studies of Novel C2-Symmetrical Chiral Tetra-Amide Compounds

Murat Sünkür(Batman Üniversitesi Fen Edebiyat Fakültesi)0000-0002-8513-7860
Züleyha Tiğiz(BATMAN ÜNİVERSİTESİ, FEN BİLİMLERİ ENSTİTÜSÜ)0000-0002-5884-392X
Deniz Cebe(BATMAN ÜNİVERSİTESİ)0000-0001-5860-2133
Tarık Aral(BATMAN ÜNİVERSİTESİ)0000-0002-6612-2751
Pages
1293–1301
Publication Date
2021-06-01
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AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

These receptor compounds exhibited strong complexation (with Ka up to 5787.23 M-1) and very good enantioselectivity (up to KaS/KaR= 13.98).

📌 3 Key Takeaways

🎯
Objective & Hypothesis:Two novel C2-symmetrical chiral tetraamide compounds derived from (S)-isoleucine were synthesised and their enantiomeric recognition abilities towards enantiomers of some amino acid esters and 1-arylethylamins were examined by UV-titration method.
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Key Findings & Data:Two novel C2-symmetrical chiral tetraamide compounds derived from (S)-isoleucine were synthesised and their enantiomeric recognition abilities towards enantiomers of some amino acid esters and 1-arylethylamins were examined by UV-titration method.
💡
Conclusion & Impact:These receptor compounds exhibited strong complexation (with Ka up to 5787.23 M-1) and very good enantioselectivity (up to KaS/KaR= 13.98).
🔬Design:Araştırma Makalesi
📍Scope:Comprehensive Sample
⚙️Variables:Enantiomeric recognitionon · chiral amide · C2-symmetrical amino acid esters

Abstract

Two novel C2-symmetrical chiral tetraamide compounds derived from (S)-isoleucine were synthesised and their enantiomeric recognition abilities towards enantiomers of some amino acid esters and 1-arylethylamins were examined by UV-titration method. These receptor compounds exhibited strong complexation (with Ka up to 5787.23 M-1) and very good enantioselectivity (up to KaS/KaR= 13.98).

Özet

Two novel C2-symmetrical chiral tetraamide compounds derived from (S)-isoleucine were synthesised and their enantiomeric recognition abilities towards enantiomers of some amino acid esters and 1-arylethylamins were examined by UV-titration method. These receptor compounds exhibited strong complexation (with Ka up to 5787.23 M-1) and very good enantioselectivity (up to KaS/KaR= 13.98).

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Cite This Article

Sünkür, M., Tiğiz, Z., Cebe, D., Aral, T. (2021). Synthesis and Enantiomeric Recognition Studies of Novel C2-Symmetrical Chiral Tetra-Amide Compounds. Iğdır Üniversitesi Fen Bilimleri Enstitüsü Dergisi, Cilt: 11 Sayı: 2, 1293–1301. https://doi.org/10.21597/jist.802116

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References (46)

  1. Aral H, Aral T, Çolak M, Ziyadanoğulları B, Ziyadanoğulları R,2013. C2-Symmetric chiral diamine ligands for enantiomeric recognition of amino acid esters and mandelic acid by proton NMR titration method. Turkish Journal of Chemistry, 37:374-382. doi: 10.3906/kim-1207-58
  2. Aral H, Çelik KS, Altındağ R, Aral T, 2017. Synthesis, characterization, and application of a novel multifunctional stationary phase for hydrophilic interaction/reversed phase mixed-mode chromatography. Talanta, 174:703-714. doi: 10.1016/j.talanta.2017.07.014
  3. Aydın I, Aral T, Karakaplan M, Hoşgören H, 2009. Chiral lariat ethers as membrane carriers for chiral amino acids and their sodium and potassium salts. Tetrahedron: Asymmetry, 20(2):179-183. doi: 0.1016/j.tetasy.2009.01.005
  4. Bako P, Keglevich G, Rapi Z, Toke L, 2012. The enantiomeric differentiation ability of chiral crown ethers based on carbohydrates. Current Organic Chemistry, 16:297-304. doi: 10.2174/138527212799499877
  5. Ballistreri FP, Pappalardo A, Tomaselli GA, Toscano RM, Sfrazzetro GT, 2010. Heteroditopic chiral uranyl–salen receptor for molecular recognition of amino acid ammonium salts. European Journal of Organic Chemistry, 3806-3810. doi: 10.1002/ejoc.201000566
  6. Bennesi HA, Hildebrand JH, 1949. A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. Journal of the American Chemical Society, 71(8):2703-2707. doi: 10.1021/ja01176a030
  7. Bohanon TM, Caruso PL, Denzinger S, Fink R, Mobius D, et al., 1999. Molecular recognition-induced function and competitive replacement by hydrogen-bonding interactions: Amphiphilic barbituric acid derivatives, 2,4,6-triaminopyrimidine, and related structures at the air−water interface. Langmuir, 15(1):174-184. doi: 10.1021/la980348w
  8. Chadwick DJ, Cliffe IA, Sutherland IO, Newton RF, 1984. The formation of complexes between aza derivatives of crown ethers and primary alkylammonium salts. Part 7. Chiral derivatives of aza crown ethers. Journal of the Chemical Society, Perkin Transactions 1, 1707-1717. doi: 10.1039/P19840001707
  9. Demirtas HN, Bozkurt S, Durmaz M, Yilmaz M, Sirit A, 2009. Chiral calix[4]azacrowns for enantiomeric recognition of amino acid derivatives. Tetrahedron, 65(15):3014-3018. doi: 10.1016/j.tet.2009.01.087
  10. Deniz P, Turgut Y, Toğrul M, Hoşgören H, 2011. Pyridine containing chiral macrocycles: synthesis and their enantiomeric recognition for amino acid derivatives. Tetrahedron, 67(34):6227-6232. doi: 10.1016/j.tet.2011.06.064
  11. Diederich F, 1988. Complexation of neutral molecules by cyclophane hosts. Angewandte Chemie International Edition in English, 27(3):362-386. doi: 10.1002/anie.198803621
  12. Fitzmaurice RJ, Kyne GM, Douheret D, Kilburn JD, 2002. Synthetic receptors for carboxylic acids and carboxylates. Journal of the Chemical Society, Perkin Transactions 1, 7:841-864. doi: 10.1039/B009041G
  13. Forte G, D’Urso A, Ballistreri FP, Tuscano RM, Tomaselli GA, et al., 2015. Enantiomeric recognition of α-amino acid derivatives by chiral uranyl–salen receptors. Tetrahedron Letters, 56(22):2922-2926. doi: 10.1016/j.tetlet.2015.04.092
  14. Guo S, Wang G, Ai L, 2013. Synthesis of macrocycles and their application as chiral solvating agents in the enantiomeric recognition of carboxylic acids and α-amino acid derivatives. Tetrahedron: Asymmetry, 24(8):480-491. doi: 10.1016/j.tetasy.2013.03.005
  15. Hembury GA, Borovkov VV, Inoue Y, 2008. Chirality-sensing supramolecular systems. Chemical Reviews, 108(1):1-73. doi: 10.1021/cr050005k
  16. Horvath G, Hutszthy P, Szarvas S, Szokan G, Redd JT, et al., 2000. Preparation of a new chiral pyridino-crown ether-based stationary phase for enantioseparation of racemic primary organic ammonium salts. Industrial & Engineering Chemistry Research, 39(10):3576–3581. doi: 10.1021/ie000272a
  17. Howard JA, Nonn M, Fulop F, Wenzel TJ, 2013. Enantiomeric discrimination of isoxazoline fused β-amino acid derivatives using (18-crown-6)-2,3,11,12-tetracarboxylic acid as a chiral NMR solvating agent. Chirality, 25(1):48-53. doi: 10.1002/chir.22114
  18. Izatt RM, Wang T, Hathaway JK, Zhang XX, Curtis JC, et al., 1994. Factors influencing enantiomeric recognition of primary alkylammonium salts by pyridino-18-crown-6 type ligands. Journal of Inclusion Phenomena and Molecular Recognition in Chemistry, 17(2):157-175. doi: 10.1007/BF00711856
  19. Karakaplan M, Aral T, 2005. Synthesis of new chiral crown ethers containing a (p-methoxyphenoxy)methyl moiety and their chiral recognition ability towards amino acid esters. Tetrahedron: Asymmetry, 16(12):2119-2124. doi: 10.1016/j.tetasy.2005.05.019
  20. Kizirian JC, Caille JC, Alexakis A, 2003. Conceptually new chiral tertiary C2 symmetric diamines in asymmetric synthesis. Tetrahedron Letters, 44(49):8893-8895. doi: 10.1016/j.tetlet.2003.09.171
  21. Kormos A, Moczar I, Baranyai P, Kupai J, Toth K, et al., 2013. Synthesis and enantiomeric recognition studies of a novel 5,5-dioxophenothiazine-1,9 bis(thiourea) containing glucopyranosyl groups. Tetrahedron: Asymmetry 24(1):62-65. doi: 10.1016/j.tetasy.2012.11.020
  22. Köylü MZ, Aral T, Karakaplan M, Kocakaya ŞÖ, Hoşgören H, 2011. Enantioselective complexation of chiral lariat crown ethers and chiral primary alkylammonium perchlorates. Turkish Journal of Chemistry, 35(2):171-179. doi: 10.3906/kim-1008-844
  23. Lee T, Lee W, Hyun MH, Park JH, 2010. Enantioseparation of α-amino acids on an 18-crown-6-tetracarboxylic acid-bonded silica by capillary electrochromatography. Journal of Chromatography A, 1217(8):1425-1428. doi: 10.1016/j.chroma.2009.12.064
  24. Liu TJ, Chen YY, Zhang KS, Wang D, Guo DW, et al., 2001. Enantiomeric recognition of chiral 3,3-bridged-1,1′-binaphthol dimer toward α-phenylethylamine and α-amino acid ester. Chirality, 13:595-600. doi: 10.1002/chir.1183
  25. Liu L, He C, Yang L, Huang Y, Wu Q, et al., 2014. Novel C1-symmetric chiral crown ethers bearing rosin acids groups: synthesis and enantiomeric recognition for ammonium salts. Tetrahedron, 70(50):9545-9553. doi: 10.1016/j.tet.2014.10.050
  26. Lu JT, Wu LZ, Jiang JZ, Zhang XM, 2010. Helical nanostructures of an optically active metal-free porphyrin with four optically active binaphthyl moieties: Effect of metal–ligand coordination on the morphology. European Journal of Inorganic Chemistry, 25:4000-4008. doi: 10.1002/ejic.201000358
  27. Marchi-Artzner V, Artzner F, Karthaus O, Shimomura M, Ariga K, et al., 1998. Molecular recognition between 2,4,6-triaminopyrimidine lipid monolayers and complementary barbituric molecules at the air/water interface: effects of hydrophilic spacer, ionic strength, and pH. Langmuir, 14(18):5164-5171. doi: 10.1021/la971192n
  28. Nakashima K, Iguchi R, Shinkai S, 2000. Diaza-18-crown-6-based saccharide receptor bearing two boronic acids. Possible communication between bound saccharides and metal cations. Industrial & Engineering Chemistry Research, 39(10):3479-3483. doi: 10.1021/ie000225i
  29. Paik MJ, Kang JS, Huang BY, Carey JR, Lee W, 2013. Development and application of chiral crown ethers as selectors for chiral separation in high-performance liquid chromatography and nuclear magnetic resonance spectroscopy. Journal of Chromatography A, 1274:1-5. doi: 10.1016/j.chroma.2012.11.086
  30. Pal D, Moczar I, Kormos A, Baranyai P, Ovari L, et al., 2015. Synthesis and enantiomeric recognition studies of optically active acridone bis(urea) and bis(thiourea) derivatives. Tetrahedron: Asymmetry, 26 (23):1335-1340. doi: 10.1016/j.tetasy.2015.10.004
  31. Pal D, Moczar I, Kormos A, Baranyai P, Huszthy P, 2016. Synthesis and enantiomeric recognition studies of optically active 5,5-dioxophenothiazine bis(urea) and bis(thiourea) derivatives. Tetrahedron: Asymmetry, 27(19):918-922. doi: 10.1016/j.tetasy.2016.08.002
  32. Park JY, Jin KB, Hyun MH, 2012. Liquid chromatographic resolution of 3-amino-1,4-benzodiazepin-2-ones on crown ether-based chiral stationary phases. Chirality, 24:427-431. doi: 10.1002/chir.22041
  33. Peri F, Maggi R, Palla G, Bigi F, Corradini R, et al., 1998. Discrimination properties of tetraamidic branched selectors. Journal of Chromatography A, 802(2):315-324. doi: 10.1016/S0021-9673(97)01190-4
  34. Pu L, 2004. Fluorescence of organic molecules in chiral recognition. Chemical Reviews, 104(3):1687-1716. doi: 10.1021/cr030052h
  35. Qing G, Sun T, Chen Z, Yang X, Wu X, et al., 2009. ‘Naked-eye’ enantioselective chemosensors for N-protected amino acid anions bearing thiourea units. Chirality, 21(3):363-373. doi: 10.1002/chir.20593
  36. Sipos L, Ilisz I, Aranyi A, Gecse Z, Nonn M, et al., 2012. High-performance liquid chromatographic enantioseparation of unusual isoxazoline-fused 2-aminocyclopentanecarboxylic acids on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid-based chiral stationary phases. Chirality, 24(10):817-824. doi: 10.1002/chir.22077
  37. Su X, Luo K, Xiang Q, Lan J, Xie R, 2009. Enantioselective recognitions of chiral molecular tweezers containing imidazoliums for amino acids. Chirality, 21(5):539-546. doi: 10.1002/chir.20635
  38. Şeker S, Barış D, Arslan N, Turgut Y, Pirinççioğlu N, et al., 2014. Synthesis of rigid and C2-symmetric pyridino-15-crown-5 type macrocycles bearing diamide–diester functions: Enantiomeric recognition for chiral primary organoammonium perchlorate salts. Tetrahedron: Asymmetry 25(5):411-417. doi: 10.1016/j.tetasy.2014.01.009
  39. Tang Z, Cun LF, Cui X, Mi AQ, Jiang JZ, et al., 2006. Design of highly enantioselective organocatalysts based on molecular recognition. Organic Letters, 8(7):1263-1266. doi: 10.1021/ol0529391
  40. Tsioupi DA, Stefan-van Staden RI, Kapnissi-Christodoulou CP, 2013. Chiral selectors in CE: Recent developments and applications. Electrophoresis, 34:178-204. doi: 10.1002/elps.201200239
  41. Turgut Y, Aral T, Hoşgören H, 2009. Synthesis of novel C2-symmetric chiral crown ethers and investigation of their enantiomeric recognition properties. Tetrahedron: Asymmetry, 20(19):2293-2298. doi: 10.1016/j.tetasy.2009.09.010
  42. Ulatowski F, Jurczak J, 2014. Enantiomeric recognition of carboxylic anions by a library of neutral receptors derived from α-amino acids and o-phenylenediamine. Tetrahedron: Asymmetry, 25(13):962-968. doi: 10.1016/j.tetasy.2014.06.004
  43. Wang Z, Wei S, Wang C, Sun J,. Enantioselective hydrosilylation of ketimines catalyzed by Lewis basic C2-symmetric chiral tetraamide. Tetrahedron: Asymmetry, 18(6):705-709. doi: 10.1016/j.tetasy.2007.03.008
  44. Yi YR, Kim KS, Helal A, Kim HS, 2013. Molecular recognition of ω-amino acids by thiazolobenzocrown receptors: a GABA-selective ionophore. Supramolecular Chemistry, 25:16-23. doi: 10.1080/10610278.2012.726731
  45. Zhang X, Yin J, Yoon J, 2014. Recent advances in development of chiral fluorescent and colorimetric sensors. Chemical Reviews, 114:4918–4959. doi: 10.1021/cr400568b
  46. Wang Z, Wei S, Wang C, Sun J,. Enantioselective hydrosilylation of ketimines catalyzed by Lewis basic C2-symmetric chiral tetraamide. Tetrahedron: Asymmetry, 18(6):705-709. doi: 10.1016/j.tetasy.2007.03.008