Total Synthesis and Antimicrobial Activity of a Natural Cycloheptapeptide of Marine Origin
Abstract
:1. Introduction
2. Results and Discussion
Reagents and conditions
3. Experimental
3.1. General procedure for the preparation of linear tri/tetrapeptide segments
tert-Butyloxycarbonyl-l-prolyl-l-isoleucyl-l-proline methyl ester (5)
tert-Butyloxycarbonyl-l-phenylalanyl-l-prolyl-l-prolyl-l-tyrosine methyl ester (6)
3.2. Deprotection of tripeptide unit at the carboxyl terminal
3.3. Deprotection of tetrapeptide unit at amino terminal
3.4. Procedure for the synthesis of the linear heptapeptide unit
tert-Butyloxycarbonyl-l-prolyl-l-isoleucyl-l-prolyl-l-phenylalanyl-l-prolyl-l-prolyl-l-tyrosine methyl ester (7)
3.5. Synthesis of the cyclic heptapeptide 8
Cyclo(l-prolyl-l-isoleucyl-l-prolyl-l-phenylalanyl-l-prolyl-l-prolyl-l-tyrosinyl) (8)
3.6. Biological activity studies
3.6.1. Antibacterial screening
3.6.2. Antifungal screening
4. Conclusions
Acknowledgements
- Samples Availability: Available from the authors.
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Compound | Diameter of zone of inhibition (mm) | |||||||
---|---|---|---|---|---|---|---|---|
Bacterial strains | Fungal strains | |||||||
B. sub. | S. aur. | P. aeru. | K. pneu. | C. alb. | M. audo. | A. niger | T. menta. | |
7 | 10(25)† | 14(12.5) | 22(6) | 23(6) | 21(6) | 11(6) | – | 14(6) |
8 | 13(25) | 16(12.5) | 26(6) | 28(6) | 27(6) | 15(6) | – | 18(6) |
Control * | – | – | – | – | – | – | – | – |
Gatifloxacin | 18(12.5) | 28(6) | 22(6) | 25(6) | – | – | – | – |
Griseofulvin | – | – | – | – | 20(6) | 17(6) | 18(12.5) | 20(6) |
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Dahiya, R.; Gautam, H. Total Synthesis and Antimicrobial Activity of a Natural Cycloheptapeptide of Marine Origin. Mar. Drugs 2010, 8, 2384-2394. https://doi.org/10.3390/md8082384
Dahiya R, Gautam H. Total Synthesis and Antimicrobial Activity of a Natural Cycloheptapeptide of Marine Origin. Marine Drugs. 2010; 8(8):2384-2394. https://doi.org/10.3390/md8082384
Chicago/Turabian StyleDahiya, Rajiv, and Hemendra Gautam. 2010. "Total Synthesis and Antimicrobial Activity of a Natural Cycloheptapeptide of Marine Origin" Marine Drugs 8, no. 8: 2384-2394. https://doi.org/10.3390/md8082384