scholarly journals Search for new synthetic immunosuppressants II. Tetrazole analogues of hymenistatin I.

2001 ◽  
Vol 48 (4) ◽  
pp. 1151-1154 ◽  
Author(s):  
P Zubrzak ◽  
K Kociołek ◽  
M Smoluch ◽  
J Silberring ◽  
M L Kowalski ◽  
...  
Keyword(s):  
Peptide Synthesis ◽  
Lymphocyte Proliferation ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Synthesis Method ◽  
Immunosuppressive Activity ◽  
Lymphocyte Proliferation Test

Linear and cyclic hymenistatin I (HS I) analogues with dipeptide segments Ile2-Pro3 Pro3-Pro4 and Val6-Pro7 replaced by their tetrazole analogues Ile2-psi[CN4]-Ala3', Pro3-psi[CN4]-Ala4 and Val6-psi[CN4]-Ala7 were synthesized by the solid phase peptide synthesis method and cyclized with the TBTU and/or HATU reagent. The peptides were examined for their immunosuppressive activity in the lymphocyte proliferation test (LPT).

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).

A faster solid phase peptide synthesis method using ultrasonic agitation

2019 ◽  
Vol 60 (28) ◽  
pp. 1814-1818 ◽  
Author(s):  
Grzegorz Wołczański ◽  
Halina Płóciennik ◽  
Marek Lisowski ◽  
Piotr Stefanowicz
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Synthesis Method ◽  
Ultrasonic Agitation

scholarly journals tert-Butyloxycarbonyl-protected amino acid ionic liquids and their application to dipeptide synthesis

RSC Advances ◽  
2021 ◽  
Vol 11 (44) ◽  
pp. 27603-27606
Author(s):  
Ming Chen ◽  
Xihan Yu
Keyword(s):  
Ionic Liquids ◽  
Amino Acid ◽  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Synthesis Method ◽  
Protected Amino Acid ◽  
First Time

Chemically protected amino acid ionic liquids are synthesized for the first time and employed as triple reactant/solvent/additives in a novel solid-phase peptide synthesis method.

scholarly journals Sintesis Tiga Peptida Bergugus Pelindung sebagai Prekursor Komponen Vaksin Influenza Universal

2015 ◽  
Vol 15 (2) ◽  
pp. 84 ◽  
Author(s):  
Toto Subroto ◽  
Ari Hardianto ◽  
Abdul Alim Kahari ◽  
Tika Pradnjaparamita
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Synthesis Method ◽  
Coupling Reaction ◽  
Synthesis Strategy ◽  
Helper Epitope ◽  
Universal Influenza Vaccine ◽  
Layer Chromatography ◽  
Conventional Vaccine

Current highly effective conventional vaccine to halt the spread of bird flu has not been invented yet because of susceptiblemutation of influenza virus. In spite of undergoing mutation which causes the amino acid sequence change, influenzaviruses maintain conservation at ectodomain of M2 protein, especially M2e(2-16) (SLLTEVETPIRNEW). The use ofconserved epitope M2e(2-16) in epitope-based vaccine potentially produces universal influenza vaccine. In designingepitope-based vaccine, the M2e(2-16) needs to be coupled with T helper epitope, P25, which is subsequently mentioned asM2e(2-16)-K-P25 (SLLTEVETPIRNEWGKKKL IPNASLIENCTKAEL). The M2e(2-16)-K-P25 was synthesized usingconvergent solid phase peptide synthesis strategy because of the size of the sequence. In this strategy, four peptideprecursors of M2e(2-16)-K-P25; SLLTEVETP (F1), IRNEWGK (F2), KLIPNASLI (F3), and ENCTKAEL (F4); were synthesizedin advance. After the precursors ready, coupling reaction was performed to obtain M2e(2-16)-K-P25. In the previousresearch, F3 has been obtained in high purity through Fmoc/tBu solid phase peptide synthesis method. In this conductedresearch, the three remaining precursors; F1, F2, and F4; were synthesized by the same method. Each peptide was analysedby thin layer chromatography, HPLC, and mass spectroscopy methods. F1, F2 and F4 were successfully synthesized andeach of them was detected at 1490.0, 1874.8 and 1881.9 amu, respectively. However, F1 was not possible to purify becauseof its insolubility in various solvents.

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.

A Strategy for Thioamide Incorporation During Fmoc Solid-Phase Peptide Synthesis with Robust Stereochemical Integrity

2019 ◽  
Author(s):  
luis camacho III ◽  
Bryan J. Lampkin ◽  
Brett VanVeller
Keyword(s):  
Amino Acid ◽  
Functional Groups ◽  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Side Chains ◽  
Amino Acid Side Chains ◽  
Peptide Elongation

We describe a method to protect the sensitive stereochemistry of the thioamide—in analogy to the protection of the functional groups of amino acid side chains—in order to preserve the thioamide moiety during peptide elongation.<br>

Analytical Methods for Solid Phase Peptide Synthesis

2004 ◽  
Vol 8 (4) ◽  
pp. 291-301 ◽  
Author(s):  
Giuseppina Sabatino ◽  
Mario Chelli ◽  
Alberto Brandi ◽  
Anna Papini
Keyword(s):  
Peptide Synthesis ◽  
Analytical Methods ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis
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