Helical Oligopeptides of a Quaternized Amino Acid with Tunable Chiral-Induction Ability and an Anomalous pH Response.
Identifieur interne : 001938 ( Ncbi/Checkpoint ); précédent : 001937; suivant : 001939Helical Oligopeptides of a Quaternized Amino Acid with Tunable Chiral-Induction Ability and an Anomalous pH Response.
Auteurs : Joonil Cho [Japon] ; Yasuhiro Ishida [Japon] ; Takuzo Aida [Japon]Source :
- Chemistry (Weinheim an der Bergstrasse, Germany) [ 1521-3765 ] ; 2017.
Descripteurs français
- KwdFr :
- MESH :
- métabolisme : Oligopeptides.
- synthèse chimique : Oligopeptides.
- Acides aminés, Concentration en ions d'hydrogène, Dichroïsme circulaire, Oligopeptides, Pipéridines, Structure secondaire des protéines, Stéréoisomérie.
English descriptors
- KwdEn :
- MESH :
- chemical , chemical synthesis : Oligopeptides.
- chemical , chemistry : Amino Acids, Oligopeptides, Piperidines.
- chemical , metabolism : Oligopeptides.
- Circular Dichroism, Hydrogen-Ion Concentration, Protein Structure, Secondary, Stereoisomerism.
Abstract
A series of octamer (8-mer) and hexadecamer (16-mer) oligopeptides of 4-aminopiperidine-4-carboxylic acid (Api) with l-leucine as a chiral auxiliary at their N or C termini were synthesized. By using circular dichroism spectroscopy, the conformational profiles of the peptides were systematically studied, which revealed that the α-helix-formation ability of the peptides is determined by the combination of parameters, which includes peptide length, state of the piperidine groups in the Api units, and position of the chiral auxiliary. When the piperidines were in the free-base state, the peptides showed a low propensity to form helical structures. However, the protonation and acylation of the piperidines enhanced the formation of helical structures, such that the order for helix-formation ability was protonated>acylated>free base. In terms of peptide length, the 16-mers generally showed higher helix-formation ability than the corresponding 8-mers, and one of the 16-mers showed helicity at the highest level reported thus far for oligopeptides of a similar length. It was also found that the sensitivity of the helical structure towards the state of the piperidine groups changed drastically depending on the chiral auxiliary position; the N-terminal chiral peptides were more sensitive than the C-terminal chiral analogues.
DOI: 10.1002/chem.201605460
PubMed: 28169479
Affiliations:
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By using circular dichroism spectroscopy, the conformational profiles of the peptides were systematically studied, which revealed that the α-helix-formation ability of the peptides is determined by the combination of parameters, which includes peptide length, state of the piperidine groups in the Api units, and position of the chiral auxiliary. When the piperidines were in the free-base state, the peptides showed a low propensity to form helical structures. However, the protonation and acylation of the piperidines enhanced the formation of helical structures, such that the order for helix-formation ability was protonated>acylated>free base. In terms of peptide length, the 16-mers generally showed higher helix-formation ability than the corresponding 8-mers, and one of the 16-mers showed helicity at the highest level reported thus far for oligopeptides of a similar length. It was also found that the sensitivity of the helical structure towards the state of the piperidine groups changed drastically depending on the chiral auxiliary position; the N-terminal chiral peptides were more sensitive than the C-terminal chiral analogues.</div></front></TEI><affiliations><list><country><li>Japon</li></country><region><li>Région de Kantō</li></region><settlement><li>Tokyo</li></settlement><orgName><li>Université de Tokyo</li></orgName></list><tree><country name="Japon"><region name="Région de Kantō"><name sortKey="Cho, Joonil" sort="Cho, Joonil" uniqKey="Cho J" first="Joonil" last="Cho">Joonil Cho</name></region><name sortKey="Aida, Takuzo" sort="Aida, Takuzo" uniqKey="Aida T" first="Takuzo" last="Aida">Takuzo Aida</name><name sortKey="Ishida, Yasuhiro" sort="Ishida, Yasuhiro" uniqKey="Ishida Y" first="Yasuhiro" last="Ishida">Yasuhiro Ishida</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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