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Molecules
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Peptide and Peptidomimetic: Synthesis, Purification and Characterization
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Peptide and Peptidomimetic: Synthesis, Purification and Characterization

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (29 February 2024) | Viewed by 4550

Special Issue Editors

Dr. Lucia Ferrazzano

E-Mail Website
Guest Editor
Department of Chemistry “Giacomo Ciamician”, Alma Mater Studiorum – University of Bologna, Via F. Selmi 2, 40126 Bologna, Italy
Interests: peptide; oligonucleotide; peptidomimetic; green peptide synthesis; stereopure oligonucleotide synthesis; green chemistry; cross-coupling reactions; organic chemistry
Dr. Laura Zaccaro

E-Mail Website
Guest Editor
Institute of Biostructures and Bioimaging, via P. Castellino 111, 80131 Naples, Italy
Interests: peptides; peptidomimetics; glycopeptides; synthesis; structure-activity relationship studies
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

In recent times, peptides and peptidomimetic molecules have regained significant attention due to their potential as biologically active agents for treating various diseases. Peptides play a central role in biological processes, while peptidomimetics offer valuable synthetic alternatives, boasting improved stability and functionality. Diverse synthetic methodologies, including solid-phase, liquid-phase and solution-phase approaches, are currently employed for peptide synthesis, with technique preference determined by the sequence length and composition. Introducing structural modifications to peptide backbones or substituting specific functional groups with isosteric moieties, aided by rational design and computer modeling, presents opportunities to surmount inherent peptide limitations. This approach preserves efficacy, yielding compounds with reduced side effects, enhanced activity and heightened selectivity. Alongside innovative and environmentally friendly synthetic pathways, purification remains pivotal for isolating target peptides or peptidomimetics from impurities. Consequently, characterization becomes indispensable to verify the synthesized molecules' identity and attributes. Nuclear magnetic resonance (NMR), mass spectrometry and circular dichroism (CD), among other analytical techniques, contribute to this validation process.

This Special Issue is dedicated to compiling contributions that showcase significant outcomes in the synthesis, purification and characterization of peptides and peptidomimetics. Possible applications span chemical synthesis, analytical chemistry and material science. We also encourage discussions on inventive green approaches to established peptide and peptidomimetic synthesis, purification and characterization techniques. 

All forms of contributions, including original research, reviews, communications and perspectives, are welcomed within this thematic domain.

Dr. Lucia Ferrazzano
Dr. Laura Zaccaro
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • peptide chemistry
  • peptidomimetic chemistry
  • peptide synthesis
  • peptide purification
  • peptide characterization
  • peptidomimetic synthesis
  • peptidomimetic purification
  • peptidomimetic characterization

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Published Papers (2 papers)

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Research

12 pages, 8857 KiB  
Article
The Role of the Unbinding Cycle on the Coordination Abilities of the Bi-Cyclopeptides toward Cu(II) Ions
by Alicja Lisowska, Paulina Świątek, Filip Dębicki, Agnieszka Lewińska, Aleksandra Marciniak, Lorenzo Pacini, Anna Maria Papini and Justyna Brasuń
Molecules 2024, 29(10), 2197; https://doi.org/10.3390/molecules29102197 - 8 May 2024
Viewed by 877
Abstract
Bicyclic peptides have attracted the interest of pharmaceutical companies because of their remarkable properties, putting them on a new path in medicine. Their conformational rigidity improves proteolytic stability and leads to rapid penetration into tissues via any possible route of administration. Moreover, elimination [...] Read more.
Bicyclic peptides have attracted the interest of pharmaceutical companies because of their remarkable properties, putting them on a new path in medicine. Their conformational rigidity improves proteolytic stability and leads to rapid penetration into tissues via any possible route of administration. Moreover, elimination of renal metabolism is of great importance, for example, for people with a history of liver diseases. In addition, each ring can function independently, making bicyclic peptides extremely versatile molecules for further optimization. In this paper, we compared the potentiometric and spectroscopic properties studied by UV–vis, MCD, and EPR of four synthetic analogues of the bi-cyclic peptide c(PKKHP-c(CFWKTC)-PKKH) (BCL). In particular, we correlated the structural and spectral properties of complexes with coordinating abilities toward Cu(II) ions of MCL1 (Ac-PKKHPc(CFWKTC)PKKH-NH2) that contains the unbinding cycle and N- and C-terminal linear parts with two histidine residues, one per part; two monocyclic ligands containing one histidine residue, both in the N-terminal position, i.e., MCL2 (Ac-PKKHPc(CFWKTC)PKKS-NH2) and in the C-terminal position, i.e., MCL3 (Ac-PKKSPc(CFWKTC)PKKH-NH2), respectively; and the linear structure LNL (Ac-PKKHPSFWKTSPKKH-NH2). Potentiometric results have shown that the bicyclic structure promotes the involvement of the side chain imidazole donors in Cu(II) binding. On the other hand, the results obtained for the mono-cyclic analogues lead to the conclusion that the coordination of the histidine moiety as an anchoring group is promoted by its location in the peptide sequence further from the nonbinding cycle, strongly influencing the involvement of the amide donors in Cu(II) coordination. Full article
(This article belongs to the Special Issue Peptide and Peptidomimetic: Synthesis, Purification and Characterization)
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15 pages, 1022 KiB  
Article
Fast Solution-Phase and Liquid-Phase Peptide Syntheses (SolPSS and LPPS) Mediated by Biomimetic Cyclic Propylphosphonic Anhydride (T3P®)
by Alexia Mattellone, Dario Corbisiero, Paolo Cantelmi, Giulia Martelli, Chiara Palladino, Alessandra Tolomelli, Walter Cabri and Lucia Ferrazzano
Molecules 2023, 28(20), 7183; https://doi.org/10.3390/molecules28207183 - 19 Oct 2023
Viewed by 3281
Abstract
The growing applications of peptide-based therapeutics require the development of efficient protocols from the perspective of an industrial scale-up. T3P® (cyclic propylphosphonic anhydride) promotes amidation in the solution-phase through a biomimetic approach, similar to the activation of carboxylic moiety catalyzed by ATP-grasp [...] Read more.
The growing applications of peptide-based therapeutics require the development of efficient protocols from the perspective of an industrial scale-up. T3P® (cyclic propylphosphonic anhydride) promotes amidation in the solution-phase through a biomimetic approach, similar to the activation of carboxylic moiety catalyzed by ATP-grasp enzymes in metabolic pathways. The T3P® induced coupling reaction was applied in this study to the solution-phase peptide synthesis (SolPPS). Peptide bond formation occurred in a few minutes with high efficiency and no epimerization, generating water-soluble by-products, both using N-Boc or N-Fmoc amino acids. The optimized protocol, which was successfully applied to the iterative synthesis of a pentapeptide, also allowed for a decrease in the solvent volume, thus improving process sustainability. The protocol was finally extended to the liquid-phase peptide synthesis (LPPS), where the isolation of the peptide was performed using precipitation, thus also showing the suitability of this coupling reagent to this emerging technique. Full article
(This article belongs to the Special Issue Peptide and Peptidomimetic: Synthesis, Purification and Characterization)
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