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Synthesis of a Cyclooctapeptide, Cyclopurpuracin, and Evaluation of Its Antimicrobial Activity.

ABSTRACT: Cyclopurpuracin is a cyclooctapeptide isolated from the methanol extract of Annona purpurea seeds with a sequence of cyclo-Gly-Phe-Ile-Gly-Ser-Pro-Val-Pro. In our previous study, the cyclisation of linear cyclopurpuracin was problematic; however, the reversed version was successfully cyclised even though the NMR spectra revealed the presence of a mixture of conformers. Herein, we report the successful synthesis of cyclopurpuracin using a combination of solid- and solution-phase synthetic methods. Initially, two precursors of cyclopurpuracin were prepared, precursor linear A (NH₂-Gly-Phe-Ile-Gly-Ser(t-Bu)-Pro-Val-Pro-OH) and precursor linear B (NH-Pro-Gly-Phe-Ile-Gly-Ser(t-Bu)-Pro-Val-OH, and various coupling reagents and solvents were trialled to achieve successful synthesis. The final product was obtained when precursors A and B were cyclised using the PyBOP/NaCl method, resulting in a cyclic product with overall yields of 3.2% and 3.6%, respectively. The synthetic products were characterised by HR-ToF-MS, ¹H-NMR, and ¹³C-NMR, showing similar NMR profiles to the isolated product from nature and no conformer mixture. The antimicrobial activity of cyclopurpuracin was also evaluated for the first time against S. aureus, E. coli, and C. albicans, showing weak activity with MIC values of 1000 µg/mL for both synthetic products, whereas the reversed cyclopurpuracin was more effective with an MIC of 500 µg/mL.

SUBMITTER: Maharani R

PROVIDER: S-EPMC10301653 | biostudies-literature | 2023 Jun

REPOSITORIES: biostudies-literature

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Synthesis of a Cyclooctapeptide, Cyclopurpuracin, and Evaluation of Its Antimicrobial Activity.

Maharani Rani R Yayat Hasna Noer Agus HNA Hidayat Ace Tatang AT Al Anshori Jamaludin J Sumiarsa Dadan D Farabi Kindi K Mayanti Tri T Nurlelasari Harneti Desi D Supratman Unang U

Molecules (Basel, Switzerland) 20230615 12

Cyclopurpuracin is a cyclooctapeptide isolated from the methanol extract of <i>Annona purpurea</i> seeds with a sequence of cyclo-Gly-Phe-Ile-Gly-Ser-Pro-Val-Pro. In our previous study, the cyclisation of linear cyclopurpuracin was problematic; however, the reversed version was successfully cyclised even though the NMR spectra revealed the presence of a mixture of conformers. Herein, we report the successful synthesis of cyclopurpuracin using a combination of solid- and solution-phase synthetic ...[more]

PMID: 37375334

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Dataset Information

Synthesis of a Cyclooctapeptide, Cyclopurpuracin, and Evaluation of Its Antimicrobial Activity.

Publications

Synthesis of a Cyclooctapeptide, Cyclopurpuracin, and Evaluation of Its Antimicrobial Activity.

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