UNNATURAL AMINO ACIDS (UAA’S): A TRENDY SCAFFOLD FOR PHARMACEUTICAL RESEARCH
Unnatural amino acids synthesis is a region of research that has gained a lot of interest in modern years. The accessibility of different synthetic routes for new unnatural amino acid derivatives and related compounds will be a critical point in the designning of novel molecules that impersonate the conformation of the natural, active peptides. These molecules (peptidomimetics) are specially designed to show the high receptor affinity and selectivity with enhanced bioavailability and metabolic stability of the drug molecule. Thus, this review focuses on detailed synthetic methods and analogues leading to synthesize variety of unnatural amino acids including various schemes that includes enantioselective synthesis and microwave-assisted synthesis also.
2. Samuel Gellma, “Efficient Method of Synthesizing Gamma Amino Acids for Applications in Medicine,Materials, Healthcare”, U.S. Patent No. 8,269,039, 2012
3. Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. 1993, 32, 1244.
4. Wang, L.; Schultz, P.G. Chem. Commun., 2002, 43, 11623.
5. Garner, P.; Park, J.M. Org. Synth. 1992, 70, 18.
6. Burger's Medicinal Chemistry and Drug Discovery, Volume 1, Drug Discovery, 6th Ed., John Wiley & Sons: New York, 2005.
7. Bonner, G.G.; Davis, P.; Stropova, C.; Ferguson, R.; Yamamura, H.I.; Porreca, F.; Hruby, V.J. Peptides, 1997, 18, 93.
8. Marshall, S.A.; Lazar, G.A.; Chirino, A.; Desjarlais, J.R. Drug Discov. Today, 2003, 8, 212.
9. Adessi, C.; Soto, C. Curr. Med. Chem., 2002, 9, 963.
10. Eggelte T. A., Koning H. D., Huisman H. O.,“Diels-Alder reaction of furan with some dienophiles”, Tetrahedron 1973,29,2491-2493.
11. Wagle D. R., Monteleone M. G., Krishnan L., Manhas M. S., Bose A. K.,“Novel synthesis of optically active morpholines” J. Chem. Soc., Chem. Commun, 1989,915-916.
12. Varma R. S., Varma M., Chatterjee A. K.,“Microwave-assisted deacetylation on alumina: a simple deprotection method” J. Chem. Soc. Perkin Trans., 1993,999-1000.
13. Crawford L. A., Bown A. W. , Breitkreuz K. E. , Cuine F. C., “The Synthesis of y-Aminobutyric Acid in Response to Treatments Reducing Cytosolic pH”,Plant Physiol., 1994,104,865-871.
14. Coles M. P., Gibson V. C., Mazzariol L., North M., Teasdale W. G., Williams C. M., Zamunerb D.,“Amino acid derived homochiral polymers via ring-opening metathesis polymerisation” J. Chem. Soc., Chem. Commun, 1994,2505-2506.
15. Ortiz A. D., Barra E. D., Hoz A., Prieto P., Moreno A.,“Cycloadditions of ketene acetals under microwave irradiation in solvent-free conditions” J. Chem. Soc. Perkin Trans., 1994, 3595-3578.
16. Hanessian, S.; Yang, R.-Y. Tetrahedron Lett., 1996, 37, 5273.
17. Tanaka, K.; Ahn, M.; Watanabe, Y.; Fuji, K. Tetrahedron Asymmetry, 1996, 7, 1771.
18. Södergren, M.J.; Andersson P.G.; Tetrahedron Lett., 1996, 37, 7577.
19. Ondrus V., Fisera L.,“Synthesis and 1,3-dipolar cycloaddition reactions of chiral maleimides”, Molecules, 1997,2,49–56.
20. Borah H. N., Boruah R. C., Sandhu J. S.,“Microwave-induced one-pot synthesis of N-carboxyalkyl Maleimides and Phthalimides” J. Chem. Research (S),1998, 272-273.
21. Drury W. J., Ferraris D., Cox C., Young B., Lectka T.,“A novel synthesis of alpha-amino acid derivatives through catalytic, enantioselective ene reactions of alpha-imino esters” J. Am. Chem. Soc., 1998, 120,11006-11007.
22. Padrón, J.M.; Kokotos, G.; Martín, T.; Markidis, T.; Gibbons, W.A.; Martín V.A. Tetrahedron Asymmetry, 1998, 9, 3381.
23. Shieh, W.-C.; Xue, S.; Reel, N.; Wu, R.; Fitt, R.; Repi
This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
Authors who publish with this journal agree to the following terms:
- Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution-NonCommercial 4.0 International (CC BY-NC 4.0). that allows others to share the work with an acknowledgment of the work's authorship and initial publication in this journal.
- Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgment of its initial publication in this journal.
- Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (See The Effect of Open Access).