Binol Based Chirality Conversion Reagents for Underivatized Amino Acids
Affiliation(s)
Synthesis and Chemosensor Lab, Department of Chemistry, Karunya University, Coimbatore, India. College of Chemistry and Chemical Engineering, Liaoning Key Laboratory for the Synthesis and Application of Functional Compounds, Bohai University, Jinzhou, China.
Synthesis and Chemosensor Lab, Department of Chemistry, Karunya University, Coimbatore, India. College of Chemistry and Chemical Engineering, Liaoning Key Laboratory for the Synthesis and Application of Functional Compounds, Bohai University, Jinzhou, China.
ABSTRACT
Four binol based pyrrole carboxamide chiral receptors has been synthesized and effectively used as a Chirality Conversion Reagent (CCR) for underivatized amino acids. Three points of interactions take place for the conversion process. They are the reversible imine formation, the internal resonance assisted Hydrogen Bonding (RAHB) and the additional hydrogen bonds between the amino acids and the heterocylic moiety of the pendant groups. The conversion efficiency of all the receptors was found to be comparable with those of the receptors reported earlier.
Four binol based pyrrole carboxamide chiral receptors has been synthesized and effectively used as a Chirality Conversion Reagent (CCR) for underivatized amino acids. Three points of interactions take place for the conversion process. They are the reversible imine formation, the internal resonance assisted Hydrogen Bonding (RAHB) and the additional hydrogen bonds between the amino acids and the heterocylic moiety of the pendant groups. The conversion efficiency of all the receptors was found to be comparable with those of the receptors reported earlier.
KEYWORDS
Binol Based Receptors; Chiral Recognition; Amino Acids; Amino Alcohols; Chiral Inversion; 1H-NMR
Binol Based Receptors; Chiral Recognition; Amino Acids; Amino Alcohols; Chiral Inversion; 1H-NMR
Cite this paper
Velmurugan, K. , Tang, L. and Nandhakumar, R. (2014) Binol Based Chirality Conversion Reagents for Underivatized Amino Acids. International Journal of Organic Chemistry, 4, 40-47. doi: 10.4236/ijoc.2014.41006.
Velmurugan, K. , Tang, L. and Nandhakumar, R. (2014) Binol Based Chirality Conversion Reagents for Underivatized Amino Acids. International Journal of Organic Chemistry, 4, 40-47. doi: 10.4236/ijoc.2014.41006.
References
[1] Collins, A.N., Sheldrake, G.N. and Crosby, J. (1997) Chirality in Industry. Wiley and Sons, Chichester. [2] Kazlauskas, R.J. (2006) Engineering a Multipurpose Catalyst. Nature Chemical Biology, 2, 514-515.
http://dx.doi.org/10.1038/nchembio1006-514 [3] Nandanwar, H.S., Gurinder, S., Hoondal, G.S. and Vohra, R.M. (2005) Enzymatic Production of D-Amino Acids. In: Barredo, J.L., Ed., Microbial Enzymes and Biotransformations, 91-104. [4] Maruoka, K. and Ooi, T. (2003) Enantioselective Amino Acid Synthesis by Chiral Phase-Transfer Catalysis. Chemical Reviews, 103, 3013-3028.
http://dx.doi.org/10.1021/cr020020e [5] Kemperman, G.J., Zhu, J., Klunder, A.J.H. and Zwanenburg, B. (2000) Clathration-Induced Asymmetric Transformation of Cefadroxil. Organic Letters, 2, 2829-2831.
http://dx.doi.org/10.1021/ol006261v [6] Vedha-Peters, K., Gunawardana, M., Rozzell, J.D. and Novick, S.J. (2006) Creation of a Broad-Range and Highly Stereoselective d-Amino Acid Dehydrogenase for the One-Step Synthesis of d-Amino Acids. Journal of American Chemical Society, 128, 10923-10929.
http://dx.doi.org/10.1021/ja0603960 [7] Kimura, T., Vassilev, V.P., Shen, G.-J. and Wong, C.H. (1997) Enzymatic Synthesis of β-Hydroxy-α-Amino Acids Based on Recombinant d- and l-Threonine Aldolases. Journal of American Chemical Society, 119, 11734-11742.
http://dx.doi.org/10.1021/ja9720422 [8] Turner, N.J. (2004) Enzyme Catalysed Deracemisation and Dynamic Kinetic Resolution Reactions. Current Opinion in Chemical Biology, 8, 114-119.
http://dx.doi.org/10.1016/j.cbpa.2004.02.001 [9] Zhang, X.X., Bradshaw, J.S. and Izatt, R.M. (1997) Enantiomeric Recognition of Amine Compounds by Chiral Macrocyclic Receptors. Chemical Reviews, 97, 3313-3362.
http://dx.doi.org/10.1021/cr960144p [10] Breccia, P., Van Gool, M., Perez-Fernandez, R., Martin-Santamaria, S., Gago, F., Prados, P. and Mendoza, J. (2003) Guanidinium Receptors as Enantioselective Amino Acid Membrane Carriers. Journal of American Chemical Society, 125, 8270-8284.
http://dx.doi.org/10.1021/ja026860s [11] Oliva, A.I., Simon, L., Hernandez, J.V., Muniz, F.M., Lithgow, A., Jimenez, A. and Moran, J.R. (2002) Enantioselective Recognition of α-Amino Acid Derivatives with a Cis-Tetrahydrobenzoxanthene Receptor. Journal of Chemical Society, Perkin Transactions, 2, 1050-1052.
http://dx.doi.org/10.1039/b203054c [12] Yang, Y., Kochoyan, M., Burgstaller, P., Westhof, E. andFamulok, M. (1996) Structural Basis of Ligand Discrimination by Two Related RNA Aptamers Resolved by NMR Spectroscopy. Science, 272, 1343-1347.
http://dx.doi.org/10.1126/science.272.5266.1343 [13] Osawa, T., Shirasaka, K., Matsui, T., Yoshihara, S., Akiyama, T., Hishiya, T., Asanuma, H. and Komiyama, M. (2006) Importance of the Position of Vinyl Group on β-Cyclodextrin for the Effective Imprinting of Amino Acid Derivatives and Oligopeptides in Water. Macromolecules, 39, 2460-2466.
http://dx.doi.org/10.1021/ma060064f [14] Okuno, H., Kitano, T., Yakabe, H., Kishimoto, M., Deore, B.A., Siigi, H. and Nagaoka, T. (2002) Characterization of Overoxidized Polypyrrole Colloids Imprinted with l-Lactate and Their Application to Enantioseparation of Amino Acids. Analytical Chemistry, 74, 4184-4190.
http://dx.doi.org/10.1021/ac025822o [15] Reeve, T.B., Cros, J.P., Gennari, C., Piarulli, U. and Vries, J.G. (2006) A Practical Approach to the Resolution of Racemic N-Benzyl α-Amino Acids by Liquid-Liquid Extraction with a Lipophilic Chiral Salen-Cobalt(III) Complex. Angewandte Chemie International Edition, 118, 2509-2513. [16] Chin, J., Lee, S.S., Lee, K.J., Park, S. and Kim, D.H. (1999) A Metal Complex That Binds Alpha-Amino Acids with High and Predictable Stereospecificity. Nature, 401, 254-257.
http://dx.doi.org/10.1038/45751 [17] Park, H., Kim, K.M., Lee, A., Ham, S., Nam, W. and Chin, J. (2007) Bioinspired Chemical Inversion of l-Amino Acids to d-Amino Acids. Journal of American Chemical Society, 129, 1518-1519.
http://dx.doi.org/10.1021/ja067724g [18] Tang, L., Ga, H., Kim, J., Choi, S., Nandhakumar, R. and Kim, K.M. (2008) Chirality Conversion and Enantioselective Extraction of Amino Acids by Imidazolium-Based Binol-Aldehyde. Tetrahedron Letters, 49, 6914-6916.
http://dx.doi.org/10.1016/j.tetlet.2008.09.117 [19] Nandhakumar, R., Ryu, J., Park, H., Tang, L., Choi, S. and Kim, K.M. (2008) Effects of Ring Substituents on Enantioselective Recognition of Amino Alcohols and Acids in Uryl-Based Binol Receptors. Tetrahedron, 64, 7704-7708.
http://dx.doi.org/10.1016/j.tet.2008.06.029 [20] Park, H., Nandhakumar, R., Hong, J., Ham, S., Chin, J. and Kim, K.M. (2008) Stereoconversion of Amino Acids and Peptides in Uryl-Pendant Binol Schiff Bases. Chemistry-A European Journal, 14, 9935-9942.
http://dx.doi.org/10.1002/chem.200801036 [21] Park, H., Hong, J., Ham, S., Nandhakumar, R. and Kim, K.M. (2009) Chirality Conversion of Dipeptides in the Schiff Bases of Binol Aldehydes with Multiple Hydrogen Bond Donors. Bulletin-Korean Chemical Society, 30, 409-414.
http://dx.doi.org/10.5012/bkcs.2009.30.2.409 [22] Meyer, C.D., Joiner, C.S. and Stoddart, J.F. (2007) Template-Directed Synthesis Employing Reversible Imine Bond Formation. Chemical Society Reviews, 36, 1705-1723.
http://dx.doi.org/10.1039/b513441m [23] Feuster, E.K. and Glass, T.E. (2003) Detection of Amines and Unprotected Amino Acids in Aqueous Conditions by Formation of Highly Fluorescent Iminium Ions. Journal of American Chemical Society, 125, 16174-16175.
http://dx.doi.org/10.1021/ja036434m [24] Nandhakumar, R., Soo, A.Y., Hong, J., Ham, S. and Kim, K.M. (2009) Enantioselective Recognition of 1,2-Aminoalcohols by the Binol Receptor Dangled with Pyrrole-2-Carboxamide and Its Analogues. Tetrahedron, 65, 666-671.
http://dx.doi.org/10.1016/j.tet.2008.11.022 [25] Catalan, J., Elguero, J., Flammang, R. and Maquestiau, A. (1983) The Relative Basicities of Imidazole and Benzimidazole. Angewandte Chemie International Edition in English, 22, 323-324.
http://dx.doi.org/10.1002/anie.198303231
[1] Collins, A.N., Sheldrake, G.N. and Crosby, J. (1997) Chirality in Industry. Wiley and Sons, Chichester. [2] Kazlauskas, R.J. (2006) Engineering a Multipurpose Catalyst. Nature Chemical Biology, 2, 514-515.
http://dx.doi.org/10.1038/nchembio1006-514 [3] Nandanwar, H.S., Gurinder, S., Hoondal, G.S. and Vohra, R.M. (2005) Enzymatic Production of D-Amino Acids. In: Barredo, J.L., Ed., Microbial Enzymes and Biotransformations, 91-104. [4] Maruoka, K. and Ooi, T. (2003) Enantioselective Amino Acid Synthesis by Chiral Phase-Transfer Catalysis. Chemical Reviews, 103, 3013-3028.
http://dx.doi.org/10.1021/cr020020e [5] Kemperman, G.J., Zhu, J., Klunder, A.J.H. and Zwanenburg, B. (2000) Clathration-Induced Asymmetric Transformation of Cefadroxil. Organic Letters, 2, 2829-2831.
http://dx.doi.org/10.1021/ol006261v [6] Vedha-Peters, K., Gunawardana, M., Rozzell, J.D. and Novick, S.J. (2006) Creation of a Broad-Range and Highly Stereoselective d-Amino Acid Dehydrogenase for the One-Step Synthesis of d-Amino Acids. Journal of American Chemical Society, 128, 10923-10929.
http://dx.doi.org/10.1021/ja0603960 [7] Kimura, T., Vassilev, V.P., Shen, G.-J. and Wong, C.H. (1997) Enzymatic Synthesis of β-Hydroxy-α-Amino Acids Based on Recombinant d- and l-Threonine Aldolases. Journal of American Chemical Society, 119, 11734-11742.
http://dx.doi.org/10.1021/ja9720422 [8] Turner, N.J. (2004) Enzyme Catalysed Deracemisation and Dynamic Kinetic Resolution Reactions. Current Opinion in Chemical Biology, 8, 114-119.
http://dx.doi.org/10.1016/j.cbpa.2004.02.001 [9] Zhang, X.X., Bradshaw, J.S. and Izatt, R.M. (1997) Enantiomeric Recognition of Amine Compounds by Chiral Macrocyclic Receptors. Chemical Reviews, 97, 3313-3362.
http://dx.doi.org/10.1021/cr960144p [10] Breccia, P., Van Gool, M., Perez-Fernandez, R., Martin-Santamaria, S., Gago, F., Prados, P. and Mendoza, J. (2003) Guanidinium Receptors as Enantioselective Amino Acid Membrane Carriers. Journal of American Chemical Society, 125, 8270-8284.
http://dx.doi.org/10.1021/ja026860s [11] Oliva, A.I., Simon, L., Hernandez, J.V., Muniz, F.M., Lithgow, A., Jimenez, A. and Moran, J.R. (2002) Enantioselective Recognition of α-Amino Acid Derivatives with a Cis-Tetrahydrobenzoxanthene Receptor. Journal of Chemical Society, Perkin Transactions, 2, 1050-1052.
http://dx.doi.org/10.1039/b203054c [12] Yang, Y., Kochoyan, M., Burgstaller, P., Westhof, E. andFamulok, M. (1996) Structural Basis of Ligand Discrimination by Two Related RNA Aptamers Resolved by NMR Spectroscopy. Science, 272, 1343-1347.
http://dx.doi.org/10.1126/science.272.5266.1343 [13] Osawa, T., Shirasaka, K., Matsui, T., Yoshihara, S., Akiyama, T., Hishiya, T., Asanuma, H. and Komiyama, M. (2006) Importance of the Position of Vinyl Group on β-Cyclodextrin for the Effective Imprinting of Amino Acid Derivatives and Oligopeptides in Water. Macromolecules, 39, 2460-2466.
http://dx.doi.org/10.1021/ma060064f [14] Okuno, H., Kitano, T., Yakabe, H., Kishimoto, M., Deore, B.A., Siigi, H. and Nagaoka, T. (2002) Characterization of Overoxidized Polypyrrole Colloids Imprinted with l-Lactate and Their Application to Enantioseparation of Amino Acids. Analytical Chemistry, 74, 4184-4190.
http://dx.doi.org/10.1021/ac025822o [15] Reeve, T.B., Cros, J.P., Gennari, C., Piarulli, U. and Vries, J.G. (2006) A Practical Approach to the Resolution of Racemic N-Benzyl α-Amino Acids by Liquid-Liquid Extraction with a Lipophilic Chiral Salen-Cobalt(III) Complex. Angewandte Chemie International Edition, 118, 2509-2513. [16] Chin, J., Lee, S.S., Lee, K.J., Park, S. and Kim, D.H. (1999) A Metal Complex That Binds Alpha-Amino Acids with High and Predictable Stereospecificity. Nature, 401, 254-257.
http://dx.doi.org/10.1038/45751 [17] Park, H., Kim, K.M., Lee, A., Ham, S., Nam, W. and Chin, J. (2007) Bioinspired Chemical Inversion of l-Amino Acids to d-Amino Acids. Journal of American Chemical Society, 129, 1518-1519.
http://dx.doi.org/10.1021/ja067724g [18] Tang, L., Ga, H., Kim, J., Choi, S., Nandhakumar, R. and Kim, K.M. (2008) Chirality Conversion and Enantioselective Extraction of Amino Acids by Imidazolium-Based Binol-Aldehyde. Tetrahedron Letters, 49, 6914-6916.
http://dx.doi.org/10.1016/j.tetlet.2008.09.117 [19] Nandhakumar, R., Ryu, J., Park, H., Tang, L., Choi, S. and Kim, K.M. (2008) Effects of Ring Substituents on Enantioselective Recognition of Amino Alcohols and Acids in Uryl-Based Binol Receptors. Tetrahedron, 64, 7704-7708.
http://dx.doi.org/10.1016/j.tet.2008.06.029 [20] Park, H., Nandhakumar, R., Hong, J., Ham, S., Chin, J. and Kim, K.M. (2008) Stereoconversion of Amino Acids and Peptides in Uryl-Pendant Binol Schiff Bases. Chemistry-A European Journal, 14, 9935-9942.
http://dx.doi.org/10.1002/chem.200801036 [21] Park, H., Hong, J., Ham, S., Nandhakumar, R. and Kim, K.M. (2009) Chirality Conversion of Dipeptides in the Schiff Bases of Binol Aldehydes with Multiple Hydrogen Bond Donors. Bulletin-Korean Chemical Society, 30, 409-414.
http://dx.doi.org/10.5012/bkcs.2009.30.2.409 [22] Meyer, C.D., Joiner, C.S. and Stoddart, J.F. (2007) Template-Directed Synthesis Employing Reversible Imine Bond Formation. Chemical Society Reviews, 36, 1705-1723.
http://dx.doi.org/10.1039/b513441m [23] Feuster, E.K. and Glass, T.E. (2003) Detection of Amines and Unprotected Amino Acids in Aqueous Conditions by Formation of Highly Fluorescent Iminium Ions. Journal of American Chemical Society, 125, 16174-16175.
http://dx.doi.org/10.1021/ja036434m [24] Nandhakumar, R., Soo, A.Y., Hong, J., Ham, S. and Kim, K.M. (2009) Enantioselective Recognition of 1,2-Aminoalcohols by the Binol Receptor Dangled with Pyrrole-2-Carboxamide and Its Analogues. Tetrahedron, 65, 666-671.
http://dx.doi.org/10.1016/j.tet.2008.11.022 [25] Catalan, J., Elguero, J., Flammang, R. and Maquestiau, A. (1983) The Relative Basicities of Imidazole and Benzimidazole. Angewandte Chemie International Edition in English, 22, 323-324.
http://dx.doi.org/10.1002/anie.198303231