From Amino Acids to Nature-Inspired Molecular Scaffolds: Incorporation of Medium-Sized Bridged Heterocycles into a Peptide Backbone

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F14%3A33151975" target="_blank" >RIV/61989592:15310/14:33151975 - isvavai.cz</a>

Výsledek na webu

<a href="http://pubs.acs.org/doi/pdf/10.1021/jo501983j" target="_blank" >http://pubs.acs.org/doi/pdf/10.1021/jo501983j</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1021/jo501983j" target="_blank" >10.1021/jo501983j</a>

Jazyk výsledku

angličtina

Název v původním jazyce

From Amino Acids to Nature-Inspired Molecular Scaffolds: Incorporation of Medium-Sized Bridged Heterocycles into a Peptide Backbone

Popis výsledku v původním jazyce

Novel molecular scaffolds comprising two to four bridged and fused heterocycles were synthesized from amino acids using seven-membered endocyclic N-acyliminium ions as key intermediates in acid-mediated tandem reactions with internal nucleophiles. This complexity-generating synthesis proceeds with high efficiency and with full stereocontrol of the newly generated stereogenic center. These results have extended the scope of medium-sized cyclic iminium ion chemistry, making it applicable as a regio- and stereoselective synthetic strategy for the generation of complex polycyclic structures. Furthermore, its compatibility with the traditional Merrifield synthesis of peptides on solid supports allowed the incorporation of the previously unexplored conformationally restricted cyclic systems into peptides without a need to independently synthesize the scaffold.

Název v anglickém jazyce

From Amino Acids to Nature-Inspired Molecular Scaffolds: Incorporation of Medium-Sized Bridged Heterocycles into a Peptide Backbone

Popis výsledku anglicky

Novel molecular scaffolds comprising two to four bridged and fused heterocycles were synthesized from amino acids using seven-membered endocyclic N-acyliminium ions as key intermediates in acid-mediated tandem reactions with internal nucleophiles. This complexity-generating synthesis proceeds with high efficiency and with full stereocontrol of the newly generated stereogenic center. These results have extended the scope of medium-sized cyclic iminium ion chemistry, making it applicable as a regio- and stereoselective synthetic strategy for the generation of complex polycyclic structures. Furthermore, its compatibility with the traditional Merrifield synthesis of peptides on solid supports allowed the incorporation of the previously unexplored conformationally restricted cyclic systems into peptides without a need to independently synthesize the scaffold.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

<a href="/cs/project/GAP207%2F12%2F0473" target="_blank" >GAP207/12/0473: Syntéza diverzních peptidomimetik s rigidní strukturou na pevné fázi.</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2014

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Journal of Organic Chemistry

ISSN

0022-3263

e-ISSN

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Svazek periodika

79

Číslo periodika v rámci svazku

21

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

12

Strana od-do

10378-10389

Kód UT WoS článku

000344638200041

EID výsledku v databázi Scopus

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