Synthetic Evaluation of Standard and Microwave-Assisted Solid Phase Peptide Synthesis of a Long Chimeric Peptide Derived from Four Plasmodium falciparum Proteins

Varela, Yahson; Murcia, Magnolia Vanegas; Patarroyo, Manuel Elkín

doi:10.3390/molecules23112877

Cited by 9 publications

(19 citation statements)

References 35 publications

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“…The essential advantages of the microwave assisted solid phase peptide synthesis are that the reduction of coupling and deprotection required time, the decreasing of the racemization and the excellent purity of the crude peptide [26,34]. Discover SPS Microwave Peptide Synthesizer has been used for peptides synthesis in which the time required for all coupling steps was within 10 to 20 min, and for all the deprotection steps was 3min each.…”

Section: Rinkmentioning

confidence: 99%

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Microwave Assisted Peptide Synthesis of Some Rationally Designed Cell Penetrating Peptides from C-Kit Receptor

et al. 2019

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I N the interest of public health, cell-penetrating peptides (CPPs) have proven to be important way for the highly efficient intracellular delivery of bioactive cargos like peptides, proteins, and oligonucliotides. It is feasible to combine one or multiple CPPs with bioactive cargos either by direct chemical conjugation or, more rarely, as non-covalent complexes. The term bioportides was introduced to describe monomeric CPPs that are intrinsically bioactive. One of the consistent problems that may compromise the in vivo applications of CPPs and bioportides, is the stimulation of mast cell (MC) secretion. Therefore, in this study two decapeptides, S6 and S6P, has been designed from the c-kit protein, a mast cells receptor, and synthesized using the technology of microwave assisted solid phase peptide synthesis. In an attempt to find bioportides from the c-Kit protein, and studying their structure-activity relationship, the present work was carried out, investigating the effect of the presence of the phosphotyrosine moiety as an active site in the synthesized peptides.

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Section: Rinkmentioning

confidence: 99%

“…These associations produce low peptide-resin complex solvation and low reagent accessibility to reaction sites. The combination of Microwave (MW) radiation with Solid-phase synthesis strategy has been used for disrupting these associations in addition to accelerating synthesis even with long peptide sequences [33,34].…”

Section: Introductionmentioning

confidence: 99%

Microwave Assisted Peptide Synthesis of Some Rationally Designed Cell Penetrating Peptides from C-Kit Receptor

et al. 2019

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“…Both two peptides were prepared using a solid phase synthesizing method 15,24 and further identied by mass spectrometry aer HPLC purication. The peptide purity were both over 99% ( Fig.…”

Section: Design Preparation and Identication Of Xts1 Peptidesmentioning

confidence: 99%

Engineering an enhanced thrombin-based GLP-1 analog with long-lasting glucose-lowering and efficient weight reduction

Pan

Xie²,

et al. 2019

RSC Adv.

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“…Despite their utility, synthesis of some peptide sequences on larger scales can prove challenging: for example, sequences with residues prone to side reactions, bulky side chains, or repetitive motifs, which often are found in self-assembling peptides for promoting interactions that lead to the formation of higher ordered structures . Peptide aggregation, usually in the form of β-sheet structures, during synthesis tends to be the primary reason for decreased coupling efficiency. , Incomplete coupling reactions result in deletions for some fraction of amino acid residues, leading to a heterogeneous population of peptides in the final product that can be difficult to purify. , Some synthetic techniques for improving product purity include chemical ligation and fragment condensation . Shorter intermediates are synthesized and purified in solution prior to coupling for formation of longer sequences, with some tendency toward racemization and long reaction times with fragment condensation .…”

Section: Introductionmentioning

confidence: 99%

Rapid Production of Multifunctional Self-Assembling Peptides for Incorporation and Visualization within Hydrogel Biomaterials

Ford

Kloxin

2021

ACS Biomater. Sci. Eng.

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Peptides are of continued interest for therapeutic applications, from soluble and immobilized ligands that promote desired binding or uptake to self-assembled supramolecular structures that serve as scaffolds in vitro and in vivo. These applications require efficient and scalable synthetic approaches because of the large amounts of material that often are needed for studies of bulk material properties and their translation. In this work, we establish new methods for the synthesis, purification, and visualization of assembling peptides, with a focus on multifunctional collagen mimetic peptides (mfCMPs) relevant for formation and integration within hydrogel-based biomaterials. First, a methodical approach useful for the microwave-assisted synthesis of assembling peptide sequences prone to deletions was established, beginning with the identification of the deleted residues and their locations and followed by targeted use of dual chemistry couplings for those specific residues. Second, purification techniques that integrate the principles of heating and ion displacement with traditional chromatography and dialysis were implemented to improve separation and isolation of the desired multifunctional peptide product, which contained blocks for thermoresponsiveness and ionic interactions. Third, an approach for fluorescent labeling of these mfCMPs, which is orthogonal to their assembly and their covalent incorporation into a bulk hydrogel material, was established, allowing visualization of the resulting hierarchical fibrillar structures in three dimensions within hydrogels using confocal microscopy. The methods presented in this work allow the production of multifunctional peptides in scalable quantities and with minimal deletions, enabling future studies for better understanding of composition−structure−property relationships and for translating these biomaterials into a range of applications. Although mfCMPs are the focus of this work, the methods demonstrated could prove useful for other assembling peptide systems and for the production of peptides more broadly for therapeutic applications.

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Synthetic Evaluation of Standard and Microwave-Assisted Solid Phase Peptide Synthesis of a Long Chimeric Peptide Derived from Four Plasmodium falciparum Proteins

Cited by 9 publications

References 35 publications

Microwave Assisted Peptide Synthesis of Some Rationally Designed Cell Penetrating Peptides from C-Kit Receptor

Microwave Assisted Peptide Synthesis of Some Rationally Designed Cell Penetrating Peptides from C-Kit Receptor

Engineering an enhanced thrombin-based GLP-1 analog with long-lasting glucose-lowering and efficient weight reduction

Rapid Production of Multifunctional Self-Assembling Peptides for Incorporation and Visualization within Hydrogel Biomaterials

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