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

43915

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

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Last updated: 22 Jan 2023

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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%.

DOI

10.21608/ejchem.2019.12996.1818

Keywords

Antioxidant peptide, pentapeptide, SCAP1, Solid-phase peptide synthesis

Authors

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First Name

Irana

Last Name

Sabana

MiddleName

Rahmawati

Affiliation

Department of Chemistry Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km 21 Jatinangor 45363, Sumedang, West Java, Indonesia

Email

iranarahmawatisabana@gmail.com

City

Bandung Area, West Java, Indonesia

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First Name

Muhammad

Last Name

Naufal

MiddleName

Affiliation

Department of Chemistry Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km 21 Jatinangor 45363, Sumedang, West Java, Indonesia

Email

naufal0079@gmail.com

City

Bandung Area, West Java, Indonesia

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View Authors

First Name

Ika

Last Name

Wiani

MiddleName

Affiliation

Department of Chemistry Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km 21 Jatinangor 45363, Sumedang, West Java, Indonesia

Email

i.wiani@unpad.ac.id

City

Bandung Area, West Java, Indonesia

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First Name

Achmad

Last Name

Zainuddin

MiddleName

Affiliation

Department of Chemistry Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km 21 Jatinangor 45363, Sumedang, West Java, Indonesia

Email

achmadzainuddin@hotmail.com

City

Bandung Area, West Java, Indonesia

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First Name

Ace

Last Name

Hidayat

MiddleName

Affiliation

Department of Chemistry Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km 21 Jatinangor 45363, Sumedang, West Java, Indonesia

Email

hidayat_at@yahoo.com

City

Bandung Area, West Java, Indonesia

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First Name

Desi

Last Name

Harneti

MiddleName

Affiliation

Department of Chemistry Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km 21 Jatinangor 45363, Sumedang, West Java, Indonesia

Email

desi.harneti@unpad.ac.id

City

Bandung Area, West Java, Indonesia

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First Name

Nurlelasari

Last Name

Nurlelasari

MiddleName

Affiliation

Department of Chemistry Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km 21 Jatinangor 45363, Sumedang, West Java, Indonesia

Email

nurlelasari@unpad.ac.id

City

Bandung Area, West Java, Indonesia

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View Authors

First Name

Jamaludin

Last Name

Al-Anshori

MiddleName

Affiliation

Department of Chemistry Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km 21 Jatinangor 45363, Sumedang, West Java, Indonesia

Email

jamaludin.al.anshori@unpad.ac.id

City

Bandung Area, West Java, Indonesia

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First Name

Unang

Last Name

Supratman

MiddleName

Affiliation

Department 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

Email

unang.supratman@unpad.ac.id

City

Bandung Area, West Java, Indonesia

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First Name

Rani

Last Name

Maharani

MiddleName

Affiliation

Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran

Email

r.maharani@unpad.ac.id

City

Bandung

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Volume

Article Issue

Related Issue

10589

Issue Date

2020-03-01

Receive Date

2019-05-22

Publish Date

2020-03-01

Page Start

921

Page End

926

Print ISSN

0449-2285

Online ISSN

2357-0245

Article File

EJCHEM_Volume 63_Issue 3_Pages 921-926.pdf

PDF . 1.1MB

Link

https://ejchem.journals.ekb.eg/article_43915.html

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https://ejchem.journals.ekb.eg/service?article_code=43915

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Original Article

Type Code

297

Publication Type

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Publication Title

Egyptian Journal of Chemistry

Publication Link

https://ejchem.journals.ekb.eg/

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Article

Created At

22 Jan 2023

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