From Amino Acids to Nature-Inspired Molecular Scaffolds: Incorporation of Medium-Sized Bridged Heterocycles into a Peptide Backbone
The result's identifiers
Result code in 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>
Result on the web
<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>
Alternative languages
Result language
angličtina
Original language name
From Amino Acids to Nature-Inspired Molecular Scaffolds: Incorporation of Medium-Sized Bridged Heterocycles into a Peptide Backbone
Original language description
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.
Czech name
—
Czech description
—
Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
—
Result continuities
Project
<a href="/en/project/GAP207%2F12%2F0473" target="_blank" >GAP207/12/0473: Solid-phase synthesis of diversely constrained peptidomimetics.</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2014
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Journal of Organic Chemistry
ISSN
0022-3263
e-ISSN
—
Volume of the periodical
79
Issue of the periodical within the volume
21
Country of publishing house
US - UNITED STATES
Number of pages
12
Pages from-to
10378-10389
UT code for WoS article
000344638200041
EID of the result in the Scopus database
—