Regioselective incorporation of backbone constraints compatible with traditional solid-phase peptide synthesis

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F13%3A33147703" target="_blank" >RIV/61989592:15310/13:33147703 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1021/co300125m" target="_blank" >http://dx.doi.org/10.1021/co300125m</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/co300125m" target="_blank" >10.1021/co300125m</a>

Result language
angličtina
Original language name
Regioselective incorporation of backbone constraints compatible with traditional solid-phase peptide synthesis
Original language description
A protected aldehyde was attached via a two-carbon spacer to a peptide backbone amide nitrogen during a traditional Merrifield solid-phase synthesis. Acid-mediated unmasking of the aldehyde triggered the regioselective formation of cyclic N-acyliminiumsbetween the aldehyde and the neighboring peptide amide nitrogen. In the absence of an internal nucleophile, the cyclic iminiums formed dihydropyrazinones, a six-membered peptide backbone constraint between two peptide amides. In the presence of an internal nucleophile, tetrahydropyrazinopyrimidinediones or tetrahydroimidazopyrazinediones were formed via tandem N-acyliminium ion cyclization-nucleophilic addition. The outcome of this nucleophilic addition was dependent on the substituent on the nitrogen nucleophile.
Czech name
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Czech description
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Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2013
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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