@-Tide-Stabilized β-Hairpins

As minimalist versions of β-structure, two-stranded β-hairpins are commonly employed as platforms for assessing the interactions that stabilize β-sheets in proteins. We have found that the presence of a 1,6-dihydro-3(2H)-pyridinone moiety (the “@-unit”) as an amino acid replacement at the i − 1 or i...

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Veröffentlicht in:	Journal of organic chemistry 2005-03, Vol.70 (5), p.1865-1871
Hauptverfasser:	Phillips, Scott T, Blasdel, Landy K, Bartlett, Paul A
Format:	Artikel
Sprache:	eng
Schlagworte:	Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Hydrogen Bonding Macromolecular Substances - chemistry Organic chemistry Peptides Peptides - chemistry Preparations and properties Protein Conformation Protein Structure, Secondary Pyridones - chemistry
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container_end_page	1871
container_issue	5
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container_title	Journal of organic chemistry
container_volume	70
creator	Phillips, Scott T Blasdel, Landy K Bartlett, Paul A
description	As minimalist versions of β-structure, two-stranded β-hairpins are commonly employed as platforms for assessing the interactions that stabilize β-sheets in proteins. We have found that the presence of a 1,6-dihydro-3(2H)-pyridinone moiety (the “@-unit”) as an amino acid replacement at the i − 1 or i + 4 positions relative to a β-turn strongly stabilizes the hairpin conformation. Hybrids of this type bridge the gap between natural β-hairpins and unnatural β-sheets because the @-unit only replaces one residue in a peptide while stabilizing the hairpin conformation to a greater extent than a normal amino acid. In this report, we describe the synthesis of a variety of @-tide-templated hairpins and the NMR and CD characterization of their conformations in both polar and nonpolar solvents.
doi_str_mv	10.1021/jo047782p
format	Article
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subjects	Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Hydrogen Bonding Macromolecular Substances - chemistry Organic chemistry Peptides Peptides - chemistry Preparations and properties Protein Conformation Protein Structure, Secondary Pyridones - chemistry
title	@-Tide-Stabilized β-Hairpins
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