Use of Methionine Alkylation to Prepare Cationic and Zwitterionic Block Copolypeptide Vesicles

Flax cyclic peptides (orbitides, linusorbs (LOs)) [1-8-NαC],[1-MetO2]-linusorb B1 ([MetO2]-LO1) and [1-9-NαC],[1-MetO2]-linusorb B2 ([MetO2]-LO2) are biologically active. These LOs lack active nuclei commonly used in peptide modification. We have developed reactions to activate methionine methyl sulphide to produce stable derivatives. In these reactions, LOs are converted to sulfonium intermediates and subsequently to derivatives containing active nuclei while preserving their fundamental structures. The reaction conditions preserved cyclic peptide fundamental structure and organic solvent solubility. [Met]-LO1 and [Met]-LO2 analogues containing activated groups (-CN, -COOEt, and -NH2 ) in the form of methionine, methionine (S)-oxide, and methionine (S,S)-dioxide amino acids were synthesized and characterized by LCMS and 1D and 2D NMR spectroscopy. Coumarin orbitide complexes produced in this manner bind Eu(3+) yielding FRET compounds that absorb energy through coumarin antennae and emit photons at lanthanide wavelengths.

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Site Covalent Modification of Methionyl Peptides for the Production of FRET Complexes

Jadhav

Shen

Sammynaiken

et al. 2015

Chemistry A European J

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Synthetic polypeptides: from polymer design to supramolecular assembly and biomedical application

et al. 2017

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Synthetic polypeptides from the ring-opening polymerization of N-carboxyanhydrides (NCAs) are one of the most important biomaterials. The unique features of these synthetic polypeptides, including their chemical diversity of side chains and their ability to form secondary structures, enable their broad applications in the field of gene delivery, drug delivery, bio-imaging, tissue engineering, and antimicrobials. In this review article, we summarize the recent advances in the design of polypeptide-based supramolecular structures, including complexes with nucleic acids, micelles, vesicles, hybrid nanoparticles, and hydrogels. We also highlight the progress in the chemical design of functional polypeptides, which plays a crucial role to manipulate their assembly behaviours and optimize their biomedical performances. Finally, we conclude the review by discussing the future opportunities in this field, including further studies on the secondary structures and cost-effective synthesis of polypeptide materials.

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Ring opening polymerization of α-amino acids: advances in synthesis, architecture and applications of polypeptides and their hybrids

et al. 2020

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Use of Methionine Alkylation to Prepare Cationic and Zwitterionic Block Copolypeptide Vesicles

Cited by 5 publications

References 20 publications

Site Covalent Modification of Methionyl Peptides for the Production of FRET Complexes

Site Covalent Modification of Methionyl Peptides for the Production of FRET Complexes

Synthetic polypeptides: from polymer design to supramolecular assembly and biomedical application

Ring opening polymerization of α-amino acids: advances in synthesis, architecture and applications of polypeptides and their hybrids

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