Solid phase synthesis of peptide hydroxamic acids on poly(ethylene glycol)‐based support

Cal, Marta; Jaremko, Mariusz; Jaremko, Łukasz; Stefanowicz, Piotr

doi:10.1002/psc.2466

Cited by 7 publications

(6 citation statements)

References 32 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…General peptide synthesis SPPS of peptides was performed manually in polypropylene syringe reactors (Intavis AG) equipped with polyethylene filters, on a modified ChemMatrix resin 11 designed for synthesis of hydroxamic acid peptides. The synthesis was carried out according to the standard Fmoc procedure.…”

Section: Methodsmentioning

confidence: 99%

“…All peptides were obtained on a ChemMatrix s resin derivatized according to a procedure described recently. 11 The sequences of all peptides investigated in this study are presented in Scheme 1.…”

Section: Design and Synthesis Of Peptidesmentioning

confidence: 99%

“…The details of synthesis of peptides has been described in a separate paper. 11 The analytical data of all obtained compounds are presented in the Experimental section.…”

Section: Design and Synthesis Of Peptidesmentioning

confidence: 99%

See 2 more Smart Citations

The metallacrowns as templates for spontaneous self-assembly of polypeptides into a tetrahelical bundle

Cal

Jaremko

et al. 2013

New J. Chem.

Self Cite

View full text Add to dashboard Cite

Amphiphilic peptide sequences with b-aminohydroxamic acid (bahx) at their C-termini were complexed with Cu 2+ ions resulting in formation of stable metallacrowns composed of bahx and copper. The ESI-MS data for the obtained compounds show formation of supramolecular structures of M W approx. 7000 Da with the compositions corresponding to metallacrowns. The addition of Cu 2+ to a solution of bahx-containing peptides results in distinct changes in the CD spectra indicating a shift of their conformational equilibria toward helical structures. The experiments with enzymatic hydrolysis show that formation of metallacrown systems significantly increases the proteolytic stability of investigated peptides.

show abstract

Section: Methodsmentioning

confidence: 99%

Section: Design and Synthesis Of Peptidesmentioning

confidence: 99%

See 1 more Smart Citation

The metallacrowns as templates for spontaneous self-assembly of polypeptides into a tetrahelical bundle

Cal

Jaremko

et al. 2013

New J. Chem.

Self Cite

View full text Add to dashboard Cite

show abstract

“…All the investigated ligands were synthesized on the solid support by methods described previously and purified by preparative high‐performance liquid chromatography (HPLC). Their molecular masses and structures were confirmed by High resolution mass spectrometry (HR‐MS).…”

Section: Resultsmentioning

confidence: 99%

“…The Fmoc‐AspEDA‐NHOH is an aspartic acid's conjugate with ethylenediamine. Synthesis of this compound has been described previously …”

Section: Methodsmentioning

confidence: 99%

The mass spectrometric study on aminohydroxamic acids-based metallacrowns

2014

Self Cite

View full text Add to dashboard Cite

Electrospray ionization mass spectrometry (MS) has been widely used to detect noncovalent interactions in supramolecular compounds, especially in biological systems. In our work, we present the application of the electrospray ionization MS technique to characterize the metallamacrocycles, known as metallacrowns. This project involves investigations of the aminohydroxamic acids structure and chirality influence on formation of ternary 12-metallacrown-4 complexes. For our experiments, we used a series of β-aminohydroxamic acids and derivatives of histidinehydroxamic acid. A high stability of the studied supramolecular systems in the gas phase was confirmed by MS/MS experiments. We also proposed the fragmentation pathways for the studied compounds. Obtained results reveal that the ternary 12-metallacrown-4 formation process is not selective, and ligands of various structures and chiralities can be incorporated into these systems.

show abstract

Combinatorial Chemistry Online

Terrett

2013

Combinatorial Chemistry - an Online Journal

View full text Add to dashboard Cite

Solid phase synthesis of peptide hydroxamic acids on poly(ethylene glycol)‐based support

Cited by 7 publications

References 32 publications

The metallacrowns as templates for spontaneous self-assembly of polypeptides into a tetrahelical bundle

The metallacrowns as templates for spontaneous self-assembly of polypeptides into a tetrahelical bundle

The mass spectrometric study on aminohydroxamic acids-based metallacrowns

Combinatorial Chemistry Online

Contact Info

Product

Resources

About