Efficient microwave-assisted synthesis of ionic esterified amino acids

Molecules

Volumn 16, Issue 10, 2011, Pages 8733-8744

  Cerón Camacho, Ricardo ^a   Aburto, Jorge ^a   Montiel, Luisa E ^a   Flores, Eugenio A ^a   Cuellar, Frisia ^a   Martínez Palou, Rafael ^a  

^a INSTITUTO MEXICANO DEL PETRÓLEO   (Mexico)

Author keywords

Amino acids; Esterification; Microwave; Parallel synthesis

Indexed keywords

EID: 80054886640     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules16108733     Document Type: Article

References (35)

1. Loupy, A. Microwaves in Organic Synthesis, 2nd ed.; Wiley-VCH: Weinheim, Germany, 2006.
2. Larhed, M.; Olofsson, K. Microwave Methods in Organic Synthesis; Springer: Berlin, Germany, 2006.
3. Martínez-Palou, R. Química en Microondas; CEM Publishing: Mattews, NC, USA, 2006 (E-book in spanish).
4. Leadbeater, N. E. Microwave Heating as a Tool for Sustainable Chemistry; CRC Press: Boca Raton, FL, USA, 2011.
5. Nüechter, M.; Ondruschka, B. Tools for microwave-assisted parallel syntheses and combinatorial chemistry. Mol. Diver. 2003, 7, 253-264. (Pubitemid 38095162)
6. Martínez-Palou, R. Advances in microwave-assisted combinatorial chemistry without polymersupported reagents. Mol. Diver. 2006, 10, 435-462. (Pubitemid 46150638)
7. Kiso, H.; Yajima, H. Peptides. Synthesis, Structures and Applications, Guue, B., Ed.; Academic Press: New York, NY, USA, 1995; volume 40.
8. Paquet, A. Preparation of some long-chain N-acyl derivatives of essential amino-acids for nutritional studies. Can. J. Biochem. 1980, 58, 573-576.
9. Kawase, T.; Nishioka, Y.; Oida, T. A novel synthesis of N-alkoxycarbonyl amino acids and surfactant. Properties of their sodium salts. J. Oleo Sci. 2010, 59, 191-201.
10. Gorecki, M.; Acquaye, C. T. A.; Wilchek, M.; Votano, J. R.; Rich, A. Antisickling activity of amino acid benzyl esters. Proc. Natl. Acad. Sci. USA 1980, 77, 181-185. (Pubitemid 10142928)
11. Beltran, J. B. U.; Bonaventura, J. S. Use of cationic preservative in food products. U. S. Patent 7407679 B2, 2008.
12. Brook, M.; Chan, T. H. A simple procedure for the esterification of carboxylic-acids. Synthesis-Stuttgart 1983, 201-203.
13. Yang, Q.; Wang, X.-J.; Li, Z. Y.; Sun, L.; You, Q. D. Microwave-assisted esterification of diverse carboxylic acids and chiral amino acids. Synth. Commun. 2008, 38, 4107-4115.
14. Penney, C. L.; Shah, P.; Landi, S. A simple method for the synthesis of long-chain alkyl esters of amino-acids. J. Org. Chem. 1985, 50, 1457-1459.
15. Arai, I.; Muramatsu, I. A simple and convenient method for esterification of tryptophan and other amino-acids. J. Org. Chem. 1983, 48, 121-123.
16. Leyendecker, F.; Jesser, F.; Laucher, D. Ligand effects in enantioface differentiating 1, 4 addition to 1, 3-diphenyl-2-propen-1-one. Tetrahedron Lett. 1983, 24, 3513-3516.
17. Gibson, S.; Romero, D.; Jacobs, H. K.; Gopalan, A. S. Concurrent esterification and N-acetylation of amino acids with orthoesters: A useful reaction with interesting mechanistic implications. Tetrahedron Lett. 2010, 51, 6737-6740.
18. Hassner, A.; Alexanian, V. Synthetic methods. 12. Direct room-temperature esterification of carboxylic-acids. Tetrahedron Lett. 1978, 46, 4475-4478.
19. Zhao, H.; Song, Z.; Cowins, J. V.; Olubajo, O. Microwave-assisted esterification of N-acetyl-L-phenylalanine using modified Mukaiyama's reagents: A new approach involving ionic liquids. Int. J. Mol. Sci. 2008, 9, 33-44. (Pubitemid 351263329)
20. Sureshbabu, V. V.; Kantharaju; Krishna, G. C. Microwave irradiation accelerated rapid, efficient and high yield esterification of Boc-amino acid to Merrifield resin mediated by KF. Int. J. Chem. B 2007, 46, 1466-1469.
21. Zhang, S.; Arvidsson, P. I. Facile synthesis of N-protected amino acids assisted by microwave irradiation. Int. J. Pept. Res. Ther. 2008, 14, 219-222.
22. Vasanthakumar, G. R.; Patil, B. S.; Babu, V. V. S. Microwave-assisted facile synthesis of amino acid benzyl ester p-toluenesulfonate and hydrochloride salts. Lett. Pept. Sci. 2002, 9, 207-209. (Pubitemid 36781725)
23. Sathe, M.; Kaushik, M. P. An efficient method for the esterification of amino acids using silica chloride. Catal. Commun. 2006, 7, 644-646. (Pubitemid 43884992)
24. Biondini, D.; Brinchi, L.; Germani, R.; Goracci, L.; Savelli, G. Esterification of unprotected alpha-amino acids in ionic liquids as the reaction media. Lett. Org. Chem. 2010, 7, 39-44.
25. Kim, D.; Choi, J.; Kim, G.-J.; Seol, S. K.; Jung, S. Accelerated esterification of free fatty acid using pulsed microwaves. Biores. Technol. 2011, 102, 7229-7231.
26. Kim, D.; Choi, J.; Kim, G. J.; Seol, S. K.; Ha, Y. C.; Vijayan, M.; Jung, S.; Kim, B. H.; Lee, G. D.; Park, S. S. Microwave-accelerated energy-efficient esterification of free fatty acid with a heterogeneous catalyst. Biores. Technol. 2011, 102, 3639-3641.
27. Melo, C. A. R.; Alburquerque, C. E. R.; Carneiro, J. S. A.; Dariva, C.; Fortuny, M.; Santos, A. F.; Egues, S. M. S.; Ramos, A. L. D. Solid-acid-catalyzed esterification of oleic acid assisted by microwave heating. Ing. Eng. Chem. Res. 2010, 49, 12135-12139.
28. Herrero, M. A.; Krensner, J. M.; Kappe, C. O. Nonthermal microwave efffects revisited: On the importance of internal temperature monitoring and agitation microwave chemistry. J. Org. Chem. 2008, 73, 36-47.
29. Hosseini, M.; Stiasni, N.; Barbieri, V.; Kappe, C. O. Microwave-assisted asymmetric organocatalysis. A probe for nonthermal microwave effects and the concept of simultaneous cooling. J. Org. Chem. 2007, 72, 1417-1424.
30. Obermayer, D.; Kappe, C. O. On the importance of simultaneous infrared/fiber-optic temperature monitoring in the microwave-assisted synthesis of ionic liquids. Org. Biomol. Chem. 2010, 8, 114-121.
31. Murillo-Hernández, J. A.; García-Cruz, I.; López-Ramirez, S.; Durán-Valencia, C.; Domínguez, J. M.; Aburto, J. Aggregation behavior of heavy crude oil-ionic liquids solutions by fluorescence spectroscopy. Energy Fuels 2009, 23, 4584-4592.
32. Ware, A. M.; Waghmare, J. T.; Momin, S. A. Alkylpolyglycoside: Carbohydrate based surfactant. J. Dispersion Sci. Technol. 2007, 28, 437-444. (Pubitemid 46404240)
33. El-Sukkary, M. M. A.; Syed, N. A.; Aiad, I.; El-Azab, W. I. M. Synthesis and characterization of some alkyl polyglycosides surfactants. J. Surfactants Detergents. 2008, 11, 129-137.
34. Murguía, M. C.; Machuca, L. M.; Lurá, M. C.; Cabrera, M. I.; Grau, R. J. Synthesis and properties of novel antifungal gemini compounds derived from N-acetyl diethanolamines. J. Surfactants Detergents 2008, 11, 223-230.
35. Synthesis to the Power of 3, Anton-Paar website. Available online: http://www.anton-paar.com/monowave300/ (accessed date: 11.oct. 2011).