Synthesis of Antioxidant Peptide SCAP1 (Leu-Ala-Asn-Ala-Lys)
Sabana, I., Naufal, M., Wiani, I., Zainuddin, A., Hidayat, A., Harneti, D., Nurlelasari, N., Al-Anshori, J., Supratman, U., Maharani, R. (2020). Synthesis of Antioxidant Peptide SCAP1 (Leu-Ala-Asn-Ala-Lys). EKB Journal Management System, 63(3), 921-926. doi: 10.21608/ejchem.2019.12996.1818
Irana Rahmawati Sabana; Muhammad Naufal; Ika Wiani; Achmad Zainuddin; Ace Hidayat; Desi Harneti; Nurlelasari Nurlelasari; Jamaludin Al-Anshori; Unang Supratman; Rani Maharani. "Synthesis of Antioxidant Peptide SCAP1 (Leu-Ala-Asn-Ala-Lys)". EKB Journal Management System, 63, 3, 2020, 921-926. doi: 10.21608/ejchem.2019.12996.1818
Sabana, I., Naufal, M., Wiani, I., Zainuddin, A., Hidayat, A., Harneti, D., Nurlelasari, N., Al-Anshori, J., Supratman, U., Maharani, R. (2020). 'Synthesis of Antioxidant Peptide SCAP1 (Leu-Ala-Asn-Ala-Lys)', EKB Journal Management System, 63(3), pp. 921-926. doi: 10.21608/ejchem.2019.12996.1818
Sabana, I., Naufal, M., Wiani, I., Zainuddin, A., Hidayat, A., Harneti, D., Nurlelasari, N., Al-Anshori, J., Supratman, U., Maharani, R. Synthesis of Antioxidant Peptide SCAP1 (Leu-Ala-Asn-Ala-Lys). EKB Journal Management System, 2020; 63(3): 921-926. doi: 10.21608/ejchem.2019.12996.1818

Synthesis of Antioxidant Peptide SCAP1 (Leu-Ala-Asn-Ala-Lys)

Egyptian Journal of Chemistry
Article 80, Volume 63, Issue 3, March 2020, Page 921-926  XML PDF (1.04 MB)
Document Type: Original Article
DOI: 10.21608/ejchem.2019.12996.1818
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Authors
Irana Rahmawati Sabana1; Muhammad Naufal1; Ika Wiani1; Achmad Zainuddin1; Ace Hidayat1; Desi Harneti1; Nurlelasari Nurlelasari1; Jamaludin Al-Anshori1; Unang Supratman2; Rani Maharani email 3
1Department of Chemistry Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km 21 Jatinangor 45363, Sumedang, West Java, Indonesia
2Department of Chemistry Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km 21 Jatinangor 45363, Sumedang, West Java, Indonesia Central Laboratory Universitas Padjadjaran, Jl. Raya BandungSumedang Km 21 Jatinangor 45363, Sumedang, West Java, Indonesia
3Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran
Abstract
SCAP1 is a pentapeptide isolated from the hydrolysate of oyster (Saccostrea cucullata), which has antioxidant and anticancer properties. This study aims to find a novel strategy to obtain antioxidant peptide SCAP1 (Leu-Ala-Asn-Ala-Lys) through chemical synthesis. This study reports the first synthesis of SCAP1 through the solid phase peptide synthesis (SPPS) method with Fmoc strategy on 2-chlorotrityl chloride resin. A HATU-HOAt coupling reagent was employed in all amide bond formations and 95% TFA in water was employed to release the desired peptide from the solid support. The crude peptide was purified using successive preparative-RP-MPLC and RP-HPLC to obtain the pure peptide. The synthesized peptide was confirmed by mass spectrometry, showing a correct molecular ion peak at m/z 516.3143 (M+H)+, referring to the desired SCAP1. 1H-NMR spectra of the peptide revealed protons signals consistent to the structure of SCAP1. During the synthesis, the coupling between Ala and Asn(Trt) was not straightforward, which led to a low yield of the final product. The use of Trt-based Asn was not a suitable option, as it could cause aggregation during the synthesis, eventually leading to a poor yield of the final product. SCAP1 was obtained as a white solid with a percent yield of 8.28%.
Keywords
Antioxidant peptide; pentapeptide; SCAP1; Solid-phase peptide synthesis
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