Synthesis, Antioxidant Activity, and Structure–Activity Relationship of SCAP1 Analogues

Maharani, Rani; Hidayat, Ace Tatang; Sabana, Irana Rahmawati; Firdausi, Anastasya; Aqmarina, Alifah; Kurnia, Dikdik; Amrullah, Mufti Hanif; Zainuddin, Achmad; Harneti, Desi; Nurlelasari, Nurlelasari; Supratman, Unang

doi:10.1007/s10989-020-10061-3

Cited by 5 publications

(8 citation statements)

References 8 publications

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“…Sletten et al (2019) mentions that in addition to using a more polar solvent, lowering the value of loading resin to spread out the elongation peptides is considered effective to inhibit aggregation [13]. The first synthesis of SCAP1e by Maharani et al (2020) required multiple purification of the crude to finally obtained the peptide in 7% yield [7]. Aggregation has made the purification step even more difficult because the impurities consists of other peptides with similar properties.…”

Section: Resultsmentioning

confidence: 99%

“…The procedure of synthesis is similar to the protocol applied for the synthesis of SCAP1e reported by Maharani et al (2020) [7]. However, the resin loading time was reduced from overnight to four hours.…”

Section: Methodsmentioning

confidence: 99%

“…The synthetic effort of SCAP1has been made by Sabana et al (2020) using solid-phase method with Fmoc strategy obtaining the synthetic SCAP1 with 8.28 % yield [6]. The low yields of the products were also seen in the synthesis of SCAP1 analogues SCAP1e (Leu-Ala-Tyr-Ala-Lys) and SCAPf (Leu-Ala-Trp-Ala-Lys) with the synthetic yields of subsequent 7% and 10% [7]. The reasons for the low yield of the synthetic product were described by Sabana et al (2020) and Maharani et al (2020) due to the presence of two alanines, the selection of incorrect protecting group of asparagine, and the higher resin loading value [6][7].…”

Section: Introductionmentioning

confidence: 99%

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AN IMPROVED SYNTHESIS OF PENTAPEPTIDE (SCAP1e) USING SOLID-PHASE METHOD WITH REDUCED RESIN LOADING TIME

et al. 2021

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SCAP1e is an alanine-rich-pentapeptide, analog of SCAP1 an antioxidant peptide. The previous solid-phase synthesis on this peptide resulted in low yield of the product (7%) due to the aggregation that might occur during synthesis. The aim of the research was to resynthesize this peptide using the similar method but with a slight modification in the resin loading step. SCAP1e was successfully synthesized through solid-phase method with an improved yield 87.9% and high purity (90.2%) based on the HPLC analysis. The reduction of resin loading value from 1.2 mmol/gram to 0.63 mmol/gram has made a good impact for the improvement of the synthetic yield.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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AN IMPROVED SYNTHESIS OF PENTAPEPTIDE (SCAP1e) USING SOLID-PHASE METHOD WITH REDUCED RESIN LOADING TIME

et al. 2021

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“…In addition, nine SCAP1 analogs have been successfully synthesized using the SPPS method. The nine analogs that have been synthesized are known that asparagine residue has an important role in the antioxidant activity of the SCAP1 compound and the replacement of lysine residue with valine can increase antioxidant activity (R. Maharani et al, 2020).…”

Section: Introductionmentioning

confidence: 99%

“…Peptide synthesis can be carried out by two methods, namely the solution phase peptide synthesis method and solid-phase peptide synthesis (SPPS) as used in the research of Sabana et al, (2020) and R. Maharani et al, (2020). In solution-phase peptide synthesis, a fully protected peptide segment is needed whereas in SPPS the use of solid supports other than as a place for the extension of the peptide chain also functions as a protective group so that the group that binds to the solid support is automatically protected (Walker & Rapley, 2008).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Pentapeptide FWKVV (Phe-Trp-Lys-Val-Val) and Its Activity as Antioxidants

Yanti

Nazareth

Agustin

et al. 2021

Indo. J. Chem. Res.

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Antioxidant pentapeptides are pentapeptide compounds that have antioxidant activity. One of the pentapeptide compounds that have antioxidant activity is FWKVV. FWKVV is a linear pentapeptide with the amino acid sequence phenylalanine-tryptophan-lysine-valine-valine, which was first isolated to hydrolyzate the muscle protein of Miiuy croaker (Miichthysmiiuy). In addition to isolation, FWKVV compounds can be produced by the peptide synthesis method because this method requires a shorter time than the isolation method from natural materials. Synthesis methods commonly used are solution-phase peptide synthesis and solid-phase peptide synthesis (SPPS). However, the SPSS method is more efficient because it does not require purification in every process. The purpose of this study was to synthesize FWKVV compounds using the SPPS method and test their antioxidant activity. FWKVV has been synthesized using the SPPS method with HBTU/HOBt coupling reagent and Fmoc protective group. The FWKVV crud produced was 148.8 mg and had antioxidant activity against DPPH radicals with an IC50 value of 4.2 mg/mL.

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Total Synthesis of Cyclosenegalin A

Aloanis,

Herlina,

Hardianto

et al. 2024

ChemistryOpen

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A Pro‐Gly‐typed cyclopeptide, cyclosenegalin A, was firstly isolated from Annona senegalensis and Annona scleroderma. In this study, we reported synthesis the cycloheptapeptide with a combination of solid‐ and solution‐phase synthetic methods. This study also compared the effectiveness of β‐turn inducer type I and II in cyclosenegalin A to facilitate the cyclization process. The synthesis of cyclosenegalin A were prepared using two different sequences of linear peptides for cyclization. First sequence employed β‐turn type I inducer (Ser‐Ala‐Val‐Thr) as turning point and second sequence employed β‐turn type II inducer (Thr‐Pro‐Gly‐Leu). The successful cyclization was obtained using the linear sequence of NH2‐Ala‐Val‐Thr‐Pro‐Gly‐Leu‐Ser‐OH with β‐turn type II. The final product was obtained in 8.2 % yield with PyBOP/DIEA act as coupling agent. The synthetic cyclosenegalin A were characterized with HR‐ToFMS, 1H NMR, 13C NMR, HSQC, HMBC, TOCSY, and ROESY. The synthetic product was also evaluated for its antimicrobial activity.

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Synthesis, Antioxidant Activity, and Structure–Activity Relationship of SCAP1 Analogues

Cited by 5 publications

References 8 publications

AN IMPROVED SYNTHESIS OF PENTAPEPTIDE (SCAP1e) USING SOLID-PHASE METHOD WITH REDUCED RESIN LOADING TIME

AN IMPROVED SYNTHESIS OF PENTAPEPTIDE (SCAP1e) USING SOLID-PHASE METHOD WITH REDUCED RESIN LOADING TIME

Synthesis of Pentapeptide FWKVV (Phe-Trp-Lys-Val-Val) and Its Activity as Antioxidants

Total Synthesis of Cyclosenegalin A

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