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

2021 ◽  
Vol 9 (1) ◽  
pp. 1-7
Author(s):  
Eka Fitri Yanti ◽  
Eviyanti Nazareth ◽  
Yuana Dwi Agustin ◽  
Mohammad Rofik Usman
Keyword(s):  
Antioxidant Activity ◽  
Peptide Synthesis ◽  
Solid Phase ◽  
Muscle Protein ◽  
Solid Phase Peptide Synthesis ◽  
Synthesis Method ◽  
Synthesis Methods ◽  
Materials Synthesis ◽  
Coupling Reagent ◽  
Ic50 Value

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.

scholarly journals Sintesis Tetrapeptida PADY menggunakan Metode Fasa Padat dan Aktivitas Antioksidannya

2019 ◽  
Vol 5 (1) ◽  
Author(s):  
Rani Maharani Ph.D ◽  
Dadan Sumiarsa ◽  
Christina Marpaung ◽  
Achmad Zainuddin ◽  
Ace Tatang Hidayat ◽  
...  
Keyword(s):  
Antioxidant Activity ◽  
Peptide Synthesis ◽  
1H Nmr ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Synthesis Method ◽  
Antioxidant Assay ◽  
Rp Hplc ◽  
Amur Sturgeon ◽  
Tof Ms

Peptida antioksidan merupakan kelompok peptida yang berperan penting karena dapat menetralkan radikal bebas, sehingga dapat mencegah dan mengobati penyakit kronis. Salah satu senyawa peptida antioksidan alami yang telah ditemukan peneliti sebelumnya adalah senyawa tetrapeptida PAGY (Pro-Ala-Gly-Tyr) yang diisolasi dari gelatin kulit ikan amur sturgeon (Acipenser schrenckii) dan dilaporkan memiliki aktivitas antioksidannya dengan IC50 5.38 mg/mL dalam uji DPPH dan 0,008 mg/mL dalam uji ABTS berturut-turut. Kelompok kami telah berhasil mensintesis PAGY bersama dengan analognya yakni PSGY, PFFY, PAFY, dan PAIY dengan menggunakan metode sintesis peptida fase padat (SPPS). Pengujian aktivitas antioksidan pada senyawa hasil sintesis menunjukkan bahwa PSGY memiliki aktivitas antioksidan lebih baik dari PAGY. Pencarian analog tetrapeptida antioksidan yang lebih baik hingga saat ini masih terus dilakukan. Pada penelitian ini telah berhasil disintesis analog tetrapeptida lainnya PADY (Pro-Ala-Asp-Tyr) dengan metode sintesis peptida fase padat menggunakan strategi Fmoc/t-Bu pada resin 2-klorotritilklorida dilanjutkan dengan pengujian aktivitas antioksidannya. HATU/HOAT digunakan sebagai reagen pengkopling dalam sintesis PADY. Pemurnian krud PADY dilakukan menggunakan RP-HPLC preparatif sehingga diperoleh PADY murni seberat 14.7 mg (12.6%). Penentuan struktur peptida hasil sintesis dianalisis dengan menggunakan spektroskopi 1H-NMR dan TOF-MS. Pada pengujian aktivitas antioksidan dengan metode DPPH, PADY hasil sintesis memberikan nilai IC50 sebesar 1.850 mg/mL, yang mengindikasikan bahwa PADY menunjukkan aktivitas antioksidan yang lebih rendah daripada PAGY hasil sintesis peneliti sebelumnya. Kata kunci: Antioksidan, tetrapeptida, sintesis peptida fase padat. Antioxidant peptide is a class of peptides that play an important in neutralizing free radicals, therefore this compound can be used to prevent and treat chronic diseases. One of the natural antioxidant peptides reported by previous researcher is PAGY (Pro-Ala-Gly-Tyr), which is isolated from amur sturgeon fish (Acipenser schrenckii) gelatin that showed antioxidant activity with IC50 5.38 and 0.008 mg/mL using DPPH and ABTS assay, respectively. Our group has successfully synthesized PAGY, along with its analogues of PSGY, PFFY, PAFY, and PAIY using solid phase peptide synthesis method (SPPS). Antioxidant assay on synthesised compounds showed that PSGY has better antioxidant activity than PAGY. The search on the analogues of the antioxidant tetrapeptide was continued. From this study, a tetrapeptide analogue PADY (Pro-Ala-Asp-Tyr) has been successfully synthesised by solid phase peptide synthesis method with Fmoc/t-Bu strategy on 2-chlorotrityl chloride resin and tested for its antioxidant activity. HATU and HOAt reagents were used as the coupling reagent for the synthesis of PADY. The resulting PADY peptide solid was then purified using preparative RP-HPLC yielding PADY of 14.7 mg (12.6%). Characterisation of the synthesized compound was analysed by  1H-NMR and TOF-MS. On the antioxidant assay using DPPH method, PADY showed IC50 value of 1.850 mg/mLindicating a lower activity than the synthetic PAGY. Keywords: Antioxidant, tetrapeptide, solid phase peptide synthesis (SPPS).

scholarly journals Cover Picture: Propylphosphonic Anhydride (T3P®) as Coupling Reagent for Solid‐Phase Peptide Synthesis (11/2021)

2021 ◽  
Vol 6 (11) ◽  
pp. 2648-2648
Author(s):  
Othman Al Musaimi ◽  
Richard Wisdom ◽  
Peter Talbiersky ◽  
Beatriz G. De La Torre ◽  
Fernando Albericio
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Coupling Reagent

Propylphosphonic Anhydride (T3P®) as Coupling Reagent for Solid‐Phase Peptide Synthesis

2021 ◽  
Vol 6 (11) ◽  
pp. 2649-2657
Author(s):  
Othman Al Musaimi ◽  
Richard Wisdom ◽  
Peter Talbiersky ◽  
Beatriz G. De La Torre ◽  
Fernando Albericio
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Coupling Reagent

Evaluation of COMU as a coupling reagent for in situ neutralization Boc solid phase peptide synthesis

2012 ◽  
Vol 18 (3) ◽  
pp. 199-207 ◽  
Author(s):  
Claudia U. Hjørringgaard ◽  
Andreas Brust ◽  
Paul F. Alewood
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Coupling Reagent

scholarly journals The 9-Fluorenylmethoxycarbonyl (Fmoc) Group in Chemical Peptide Synthesis – Its Past, Present, and Future

2020 ◽  
Vol 73 (4) ◽  
pp. 271 ◽  
Author(s):  
Wenyi Li ◽  
Neil M. O'Brien-Simpson ◽  
Mohammed Akhter Hossain ◽  
John D. Wade
Keyword(s):  
Chemical Synthesis ◽  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Peptide Bond ◽  
Synthesis Methods ◽  
Protecting Group ◽  
Fmoc Group ◽  
The 1960S ◽  
The Many

The chemical formation of the peptide bond has long fascinated and challenged organic chemists. It requires not only the activation of the carboxyl group of an amino acid but also the protection of the Nα-amino group. The more than a century of continuous development of ever-improved protecting group chemistry has been married to dramatic advances in the chemical synthesis of peptides that, itself, was substantially enhanced by the development of solid-phase peptide synthesis by R. B. Merrifield in the 1960s. While the latter technology has continued to undergo further refinement and improvement in both its chemistry and automation, the development of the base-labile 9-fluorenylmethoxycarbonyl (Fmoc) group and its integration into current synthesis methods is considered a major landmark in the history of the chemical synthesis of peptides. The many beneficial attributes of the Fmoc group, which have yet to be surpassed by any other Nα-protecting group, allow very rapid and highly efficient synthesis of peptides, including ones of significant size and complexity, making it an even more valuable resource for research in the post-genomic world. This review charts the development and use of this Nα-protecting group and its adaptation to address the need for more green chemical peptide synthesis processes.

scholarly journals High-affinity sequence-selective DNA binding by iridium(iii) polypyridyl organometallopeptides

2016 ◽  
Vol 52 (6) ◽  
pp. 1234-1237 ◽  
Author(s):  
Ilaria Gamba ◽  
Iria Salvadó ◽  
Rosa F. Brissos ◽  
Patrick Gamez ◽  
José Brea ◽  
...  
Keyword(s):  
Dna Binding ◽  
Cell Lines ◽  
Peptide Synthesis ◽  
Cytotoxic Effect ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Synthesis Methods ◽  
High Affinity ◽  
Dna Binding Affinity ◽  
Selective Dna Binding

We demonstrate the application of solid-phase peptide synthesis methods for assembling polynuclear Ir(iii) organometallopeptides that exhibit high DNA-binding affinity, sequence selectivity, and high cytotoxic effect towards a set of cancer cell lines.

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