Synthesis of Assigned Structure of Cairomycin A, 6-Isopropyl-2,5-Diketopiperazine-3-Acetic Acid and Its Β-Lactam Analogue N`- (3-Methyl-1-Hydroxybutyr-2-Yl) Azetidin-2-One-4-Carboximide
DOI:
https://doi.org/10.25271/sjuoz.2019.7.4.638Keywords:
Cairomycin A, 2,5-Diketonpiperazine, β-Lactam, Azetidine, AntimicrobialAbstract
In the present investigation, the research carried out into the total synthesis of the assigned structure of cairomycin A, 6-isopropyl-2,5-diketopiperazine-3-acetic acid from its precursors L-valine and L-aspartic acid, and its analogue N`-(3-methyl-1-hydroxybutyr-2-yl)azetidin-2-one-4-carboximide from 4-vinylazetidi-2-one through two different sequence reactions. Structures of the synthesized products were identified by using chemical and physical methods such as elemental analysis, IR, 1H-NMR and MS. The obtained results were compared with those reported, it was found that neither of the synthesized compounds was Cairomycin A.
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Borthwick, A. D. (2012). 2, 5-Diketopiperazines: synthesis, reactions, medicinal chemistry, and bioactive natural products. Chemical reviews, 112(7), 3641-3716.
Brennan, J., Richardson, G., & Stoodley, R. J. (1980). Synthesis of 7-oxo-3-oxa-1-azabicyclo [3.2. 0] heptane-2-carboxylates: analogues of clavulanic acid. Journal of the Chemical Society, Chemical Communications, (2), 49a-49a.
Cavilier, F., Girand, M., Bernard, M., and Martinez, J. (2001). Original and General Strategy of Dimerization of Bioactive Molecules in Peptides: The Wave of the Future; Lebl, M., Houghten, R.A., Eds.; American Peptide society; San Diego, 152-155.
Corey, E. J., & Schmidt, G. (1979). Studies on the total synthesis of rifamycin. A method for the stereospecific synthesis of the carbonyl-conjugated 1, 3-diene unit [C (15) to C (20)]. Tetrahedron Letters, 20(25), 2317-2320.
Delaforge, M., Bouillé, G., Jaouen, M., Jankowski, C. K., Lamouroux, C., & Bensoussan, C. (2001). Recognition and oxidative metabolism of cyclodipeptides by hepatic cytochrome P450. Peptides, 22(4), 557-565.
Dinsmore, J.C., and Beshore, D.C. (2002). Recent Advances in the Synthesis of Diketopiperazines, Tetrahedron, 58(17), 3297-3312.
Fischer, P. M. (2003). Diketopiperazines in peptide and combinatorial chemistry. Journal of peptide science: an official publication of the European Peptide Society, 9(1), 9-35.
Greenstein, J.P. and Winitz, M. (1961) Chemistry of the Amino Acids. John Wiley & Sons, New York, 763.
Houston, D. R., Synstad, B., Eijsink, V. G., Stark, M. J., Eggleston, I. M., & Van Aalten, D. M. (2004). Structure-based exploration of cyclic dipeptide chitinase inhibitors. Journal of medicinal chemistry, 47(23), 5713-5720.
Kumar, A., Singh, M., & Chauhan, V.S. (1985). Synthesis of cairomycin A. The Journal of antibiotics, 38(10), 1420-1422.
Lemieux, R. U., & Rudloff, E. V. (1955). Periodate–permanganate oxidations: I. Oxidation of olefins. Canadian Journal of Chemistry, 33(11), 1701-1709.
Moriconi, E. J., & Meyer, W. C. (1971). Reaction of dienes with chlorosulfonyl isocyanate. The Journal of Organic Chemistry, 36(19), 2841-2849.
Nicholson, B., Lloyd, G. K., Miller, B. R., Palladino, M. A., Kiso, Y., Hayashi, Y., & Neuteboom, S. T. (2006). NPI-2358 is a tubulin-depolymerizing agent: in-vitro evidence for activity as a tumor vascular-disrupting agent. Anti-cancer drugs, 17(1), 25-31.
O'Neill, J. C., & Blackwell, H. E. (2007). Solid-phase and microwave-assisted syntheses of 2, 5-diketopiperazines: small molecules with great potential. Combinatorial chemistry & high throughput screening, 10(10), 857-876.
Pietsch, H. (1976). Synthese von S-Aspartyl-S-phenylalaninmethylester (aspartam) aus S-4-vinylazetidin-2-on. Tetrahedron Letters, 17(45), 4053-4056.
Schwarz, H., Bumpus, F. M., & Page, I. H. (1957). Synthesis of a Biologically Active Octapeptide Similar to Natural Isoleucine Angiotonin Octapeptide1. Journal of the American Chemical Society, 79(21), 5697-5703.
Shimi, I.R., and Fathy, Sh. (1981). Isolation of Cairomycins A and C, Antimicrobial Agents and Chemotherapy, 19(6), 941-944.
Sinha, S., Srivastava, R., De Clercq, E., & Singh, R. K. (2004). Synthesis and antiviral properties of arabino and ribonucleosides of 1, 3‐dideazaadenine, 4‐nitro‐1, 3‐dideazaadenine and diketopiperazine. Nucleosides, Nucleotides and Nucleic Acids, 23(12), 1815-1824.
Sun, X., Rai, R., MacKerell Jr, A. D., Faden, A. I., & Xue, F. (2014). Facile one-step synthesis of 2, 5-diketopiperazines. Tetrahedron Letters, 55(11), 1905-1908.
Suzuki, K., Sasaki, Y., Endo, N. O. B. U. Y. O. S. H. I., & Mihara, Y. U. I. C. H. I. (1981). Acetic acid-catalyzed diketopiperazine synthesis. Chemical and Pharmaceutical Bulletin, 29(1), 233-237.
Vollhardt, K., and Schore, N. (2007). Organic Chemistry: Structure and Function, 5th ed. New York, NY: W.H. Freeman and Company.
Wang, C., Zong, L., & Tan, C. H. (2015). Enantioselective oxidation of alkenes with potassium permanganate catalyzed by chiral dicationic bisguanidinium. Journal of the American Chemical Society, 137(33), 10677-10682.
Zervas, L., Winitz, M., & Greenstein, J. P. (1957). Studies on arginine peptides. I. Intermediates in the synthesis of N-terminal and C-terminal arginine peptides. The Journal of Organic Chemistry, 22(11), 1515-1521.
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Published
2019-12-30
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Hussain, F. H. S. (2019). Synthesis of Assigned Structure of Cairomycin A, 6-Isopropyl-2,5-Diketopiperazine-3-Acetic Acid and Its Β-Lactam Analogue N`- (3-Methyl-1-Hydroxybutyr-2-Yl) Azetidin-2-One-4-Carboximide. Science Journal of University of Zakho, 7(4), 144–151. https://doi.org/10.25271/sjuoz.2019.7.4.638
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