Sintesis Tetrapeptida MeFYAP (mePhe-Try-Ala-Pro) dengan Metode Solid Phase Peptide Synthesis debagai Kandidat Antioksidan
Abstract
ABSTRACT: Free radicals are molecules that are unpaired in their outer orbitals, free radical activity can be inhibited by antioxidants by binding and stabilizing the free radicals. Antioxidant peptides are able to ward off free radicals, one of the peptides derived from natural ingredients is the tetrapeptide FLAP (Phe-Leu-Ala-Pro) and one of its derivatives (mePhe-Try-Ala-Pro) which has been successfully modified from Sea Cucumber (Acaudia Molpadiodes) in Zheijing China. So that the tetrapeptide has the potential to be developed as an antioxidant. Isolation of peptides from nature requires large amounts of raw materials so it is considered less efficient. Therefore, in this study, a more efficient and environmentally friendly tetrapeptide (mePhe-Try-Ala-Pro) was produced, namely the solid phase synthesis method or (SPPS) with the Fmoc amino acid strategy using 2-chlorotrityl chloride resin with the help of HOBt, HBTU and reagents. DIPEA. The results showed that the synthesis was successful with the resulting tetrapeptide weight of 143.7 mg. However, based on the results of the characterization using a mass spectrophotometer and RP-HPLC, it was found that there were still impurities that needed further purification. Furthermore, the results of the antioxidant activity test on the tetrapeptide compound showed that the compound had a percent IC50 value of 17.677% indicating that the antioxidant activity of the compound was weak.
Keywords: Antioxidant, tertapeptide, solid phase peptide synthesis (SPPS)
ABSTRAK: Radikal bebas adalah molekul yang tidak berpasangan pada orbital terluarnya, aktivitas radikal bebas dapat dihambat dengan antioksidan dengan cara berikatan dan menstabilkan radikal bebas tersebut. Peptida antioksidan mampu menangkal radikal bebas, salah satu peptida yang berasal dari bahan alam adalah tetrapeptida FLAP (Phe-Leu-Ala-Pro) dan salah satu derivatnya yaitu (mePhe-Try-Ala-Pro) yang berhasil dimodifikasi dari Teripang (Acaudia Molpadiodes) di Zheijing Cina. Sehingga tetrapeptida tersebut potensial untuk dikembangkan sebagai antioksidan. Isolasi peptida dari alam memerlukan bahan baku dalam jumlah besar sehingga dinilai kurang efisien. Maka pada penelitian ini dilakukan produksi tetrapeptida (mePhe-Try-Ala-Pro) yang lebih efisien dan ramah lingkungan yaitu  dengan metode sintesis fase padat atau (SPPS) dengan strategi Fmoc asam amino menggunakan resin 2-klorotritil klorida dengan bantuan reagen HOBt, HBTU dan DIPEA. Hasil penelitian menunjukan bahwa sintesa berhasil dilakukan dengan berat tetrapeptida yang dihasilkan sebesar 143,7 mg. Namun berdasarkan hasil karakterisasi dengan spektrofotometer massa dan RP-HPLC ditemukan bahwa masih terdapat pengotor sehingga perlu dilakukan pemurnian lebih lanjut. Selanjutnya hasil uji aktivitas antioksidan pada senyawa tetrapeptida menunjukan bahwa senyawa memiliki nilai persen IC50 sebesar 17,677 % menunjukan bahwa aktivitas antioksidan senyawa tersebut lemah.
Kata Kunci: Antioksidan, tetrapeptida, sintesis peptide fase padat
Keywords
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DOI: http://dx.doi.org/10.29313/.v0i0.29899
