Polypseudopeptides with Variable Stereochemistry: Synthesis via Click-Chemistry, Postfunctionalization, and Conformational Behavior in Solution

Autor:	Stefan Hecht, Sebastian Hartwig
Rok vydání:	2009
Předmět:	chemistry.chemical_classification Dipeptide Polymers and Plastics Stereochemistry Organic Chemistry Triazole Alkyne Inorganic Chemistry chemistry.chemical_compound chemistry Materials Chemistry Gramicidin Click chemistry Side chain Peptide bond Azide
Zdroj:	Macromolecules. 43:242-248
ISSN:	1520-5835 0024-9297
Popis:	Polypseudopeptides with well-defined stereochemistries have been synthesized from readily available amino-acid-based building blocks by connecting (L,L)- or (L,D)-dipeptide AB-monomers carrying azide and alkyne termini via triazole amide-isosteres efficiently formed in the course of the "click" reaction. Deprotection of the thus-prepared lysine-based polypseudopeptides of both all-(L)- and (D)-alt-(L)-stereo- chemistries afforded water-soluble polymers with ionizable amino side chains, which could be fully labeled with pyrene chromophores via quantitative amide bond formation. The conformational behavior of the deprotected as well as the pyrene-labeled polymers was investigated using UV/vis, CD, and fluorescence spectroscopies. On one hand, the free polyamines display pH-dependent conformations in water. On the otherhand,thepyrene-labeledpolypseudopeptideschangetheirconformationinresponsetovaryingorganic solvent composition. Whereas the strictly alternating polypseudopeptides structurally resemble channel- forming peptides, such as the Gramicidin family, the incorporation of (D)-configured amino acids as well as triazole amide-isosteres should lead to interesting new materials for bioapplications.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::29dc6189f3ec63d0b040f33bf9e777f3 https://doi.org/10.1021/ma902018w Zobrazit plný text záznamu