Synthesis of Peptides Influencing Growth Hormone Release

1994 ◽  
Vol 59 (3) ◽  
pp. 707-717 ◽  
Author(s):  
Jan Hlaváček ◽  
Otto Smékal ◽  
Jan Pospíšek ◽  
Tomislav Barth
Keyword(s):  
Growth Hormone ◽  
Cyclic Peptides ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Benzyl Ester ◽  
Linear Peptide ◽  
Alkaline Conditions ◽  
Merrifield Resin ◽  
Fmoc Strategy ◽  
By Products

A solid phase peptide synthesis of 17 growth hormone (GH) releasing peptide analogues Ia - IIIc for their use in a pharmacological assay on GH release is described. While the linear peptide amides Ia - Ij were synthesized on p-methylbenzhydrylamine resin using Boc strategy, and cleaved by HF in the presence of scavengers the linear peptide amides Ik and Il were prepared on Merrifield benzyl ester type resin using Fmoc strategy and cleaved by ammonolysis. The deleted peptide amides IIa and IIb were obtained as by-products during HPLC purification of analogues Ic and Id. The linear precursors of cyclic peptides IIIa - IIIc were also prepared on Merrifield resin and cleaved under mild alkaline conditions. Their cyclization was performed in solution by diphenylphosphoryl azide.

scholarly journals Sintesis Tetrapeptida Linear (DPAP) Menggunakan Metode Sintesis Peptida Fasa Padat (SPPS) Dan Aktivitas Insektisidanya Terhadap Ulat Krop Kubis

2020 ◽  
Vol 8 (1) ◽  
pp. 6-14
Author(s):  
Eka Fitri Yanti ◽  
Rani Maharani
Keyword(s):  
Peptide Synthesis ◽  
Column Chromatography ◽  
Insecticidal Activity ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Negative Effects ◽  
Reverse Phase ◽  
Linear Peptide ◽  
Fmoc Strategy ◽  
Phase Column

Crop cabbage worm (Crocidolomia pavonana) is one of the pests that has a bad effect on the cabbage production in Indonesia. One of the efforts that has been applied to control this pest is by using bayrusil. However, the bayrusil can cause negative effects such as poisoning and environmentally polluting effects. To prevent the undesired effects, it has been developed the use of environmentally friendly insecticide and one of them is the use of insecticidal peptide. Tripsin-modulating oostatic factor (TMOF) and ist analogues is one of the peptides that has an insecticidal activity. The aim of this research is to synthesise a linear tetrapeptide (DPAP) an analogues of TMOF and to test insecticidal activities against crop cabbage worm.  A DPAP has been synthesised by Solid Phase Peptide Synthesis on 2-chlorotrytil chloride resin. Fmoc strategy was applied on the synthesis and a combination DIC/Oxime was employed in the coupling reaction.The tetrapeptidyl resin was cleaved by TFA:water:EDT (90:5:5). The peptide was purified by reverse-phase column chromatography and characterized by TOF ES-MS spectroscopy. A linear peptide was biologically tested towards the C. pavonana, showing percentage of mortality values at 1000 ppm.

Synthesis of MUC1 Peptide and Glycopeptide Dendrimers

2009 ◽  
Vol 62 (10) ◽  
pp. 1339 ◽  
Author(s):  
Candy K. Y. Chun ◽  
Richard J. Payne
Keyword(s):  
Peptide Synthesis ◽  
Tandem Repeat ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Cycloaddition Reaction ◽  
Repeat Sequence ◽  
Tandem Repeat Sequence ◽  
Multiple Copies ◽  
Fmoc Strategy

Several dendrimers possessing multiple copies of peptides and glycopeptides belonging to the MUC1 eicosapeptide tandem repeat sequence have been prepared. Fmoc-strategy solid-phase peptide synthesis was used to construct the peptides and glycopeptides, which were conjugated to suitably functionalized dendrimer cores using the copper-catalyzed azide-alkyne cycloaddition reaction to produce multivalent peptide and glycopeptide dendrimers.

Studies Toward the Total Synthesis and Stereochemical Assignment of Microspinosamide

2015 ◽  
Vol 68 (12) ◽  
pp. 1885 ◽  
Author(s):  
Gajan Santhakumar ◽  
Richard J. Payne
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Chemical Ligation ◽  
Stereochemical Assignment ◽  
Linear Peptide ◽  
Cyclic Depsipeptide ◽  
Peptide Thioester ◽  
Structural Differences

Efforts toward the total synthesis and stereochemical assignment of the cyclic depsipeptide natural product microspinosamide are described. A single diastereoisomer was targeted corresponding to the predicted structure of the natural product incorporating a (2S, 3R)-β-hydroxy-p-bromophenylalanine residue. Assembly was achieved through the initial synthesis of a cyclic depsipeptide and a linear peptide thioester fragment by solid-phase peptide synthesis, followed by fusion of the two fragments through a native chemical ligation–oxidation protocol. Extensive spectroscopic analysis showed structural differences to the isolated natural product, suggesting that a diastereoisomer of microspinosamide had been synthesised. This work lays the foundation for the future synthesis of the correct diastereoisomer.

Aqueous Microwave-Assisted Solid-Phase Peptide Synthesis Using Fmoc Strategy: In-Water Synthesis of "Difficult Sequences"

2012 ◽  
Vol 19 (11) ◽  
pp. 1231-1236 ◽  
Author(s):  
Keiko Hojo ◽  
Hideki Ichikawa ◽  
Asaki Hara ◽  
Mare Onishi ◽  
Koichi Kawasaki ◽  
...  
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Microwave Assisted ◽  
Difficult Sequences ◽  
Fmoc Strategy

An efficient mild acidolytic deprotection procedure for Boc/Bzl-based solid phase peptide synthesis

1990 ◽  
Vol 55 (7) ◽  
pp. 1792-1800 ◽  
Author(s):  
Rudolf Dölling ◽  
Peter Jeschke ◽  
Albrecht Otto ◽  
Jutta Eichler
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Benzyl Ester

Using the mild acidolytic deprotecting reagents 0.1M MSA or 0.1M TMSOTf in TFA in combination with PMB, which simultaneously accelerates the cleavage and acts as irreversible scavenger, the rate of cleavage of a model dipeptide from the appropriate Nα-Fmoc-dipeptidyl resin (polymer-bound benzyl ester, p-MBHA and BHA resin, respectively) was studied. The new deprotecting method was successfully applied to the synthesis of three Nα-halogenoacetyl modified octapeptides (I, II) and a 16-residue peptide (III). In all cases, the crude products were of the same quality as peptides obtained via the HF/10% anisole technique.

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