Sintesis Senyawa Heksapeptida Siklik Analog Pipecolisporin (Pro-Lys-Pip-Trp-
DOI:
https://doi.org/10.29313/bcsp.v3i2.8876Keywords:
Peptida, pipecolisporin, DIC/Oxyma, SPPS, LPPSAbstract
Pipecolisporin compounds isolated from the fungus Nigrospora oryzae from theroots of Triticum sp. is one of the compounds that has potential as an antimalarial with its activity against Plasmodium falciparum of 3.21 μM. The modification of the amino acid sequence to Pro-Lys-Pip-Trp-β-Ala-Phe aims to determine the best arrangement of pipecolisporin analogues as antimalarials. Analogues of pipecolisporin linear hexapeptide compounds were synthesized using the solid phase peptide synthesis (SPPS) method with the use of buffers in the form of 2-chlorotrityl chloride resins, Fmoc and Boc protective groups, and DIC, Oxyma, Dipea coupling reagent solutions. The synthesis results were obtained as much as 9 mg and then characterized using mass spectroscopy with a peak m/z of 959.5246 [M]. Analogues of linear pipecolisporin hexapetide compounds were successfully cyclized using the solution phase peptide synthesis (LPPS) method with the use of DIPEA, HATU, DCM reagent solutions. The synthesis results were characterized using mass spectroscopy with an m/z peak of 743.78 [M+H]+.
Senyawa pipecolisporin hasil isolasi jamur Nigrospora oryzae dari akar Triticum sp. merupakan salah satu senyawa yang berpotensi sebagai antimalaria dengan aktivitasnya terhadap Plasmodium falciparum sebesar 3,21 μM. Modifikasi urutan asam amino menjadi Pro-Lys-Pip-Trp-
References
[2] N. Lawrence et al., “Defense Peptides Engineered from Human Platelet Factor 4 Kill Plasmodium by Selective Membrane Disruption,” Cell Chem Biol, vol. 25, no. 9, 2018, doi: 10.1016/j.chembiol.2018.06.009.
[3] I. Fernández-Pastor et al., “Pipecolisporin, a novel cyclic peptide with antimalarial and antitrypanosome activities from a wheat endophytic nigrospora oryzae,” Pharmaceuticals, vol. 14, no. 3, 2021, doi: 10.3390/ph14030268.
[4] R. Maharani, E. F. Yanti, M. D. I. Melati, and D. Sihotang, “Synthesis of Trypsin-modulating Oostatic Factor (TMOF) and its Analogues by Solid-phase Peptide Synthesis Using DIC/Oxyma as Coupling Reagent,” Procedia Chem, vol. 17, pp. 125–131, 2015, doi: 10.1016/j.proche.2015.12.124.
[5] E. F. Yanti and R. Maharani, “Sintesis Tetrapeptida Linear (DPAP) Menggunakan Metode Sintesis Peptida Fasa Padat (SPPS) Dan Aktivitas Insektisidanya Terhadap Ulat Krop Kubis,” Indo. J. Chem. Res., vol. 8, no. 1, 2020, doi: 10.30598/10.30598//ijcr.2020.8-eka.
[6] G. Corkill and R. Rapley, “The manipulation of nucleic acids basic tools and techniques,” in Molecular Biomethods Handbook: Second Edition, 2008. doi: 10.1007/978-1-60327-375-6_1.
[7] Eka Nurjanah and Nety Kurniaty, “Sintesis Tetrapeptida Linear Phe-Leu-Ala-Pro (FLAP) sebagai Kandidat Antioksidan dengan Metode Solid Phase Peptide Synthesis (SPPS),” Jurnal Riset Farmasi, vol. 1, no. 2, 2021, doi: 10.29313/jrf.v1i2.452.
[8] R. Maharani et al., “Sintesis Tetrapeptida PSSY dengan Metode Fasa Padat,” Chimica et Natura Acta, vol. 7, no. 2, 2019, doi: 10.24198/cna.v7.n2.26156.
[9] Dita Utami and Nety Kurniaty, “Sintesis Senyawa Heksapeptida Siklik Analog Pipecolisporin (Lys-Βala-Trp-Pip-Leu-Pro) dengan Metode Kombinasi Sintesis Fase Padat dan Fase Larutan Sebagai Kandidat Antimalaria,” Bandung Conference Series: Pharmacy, vol. 2, no. 2, 2022, doi: 10.29313/bcsp.v2i2.4395.