Privileged Structures as Peptide Backbone Constrains: Polymer-Supported Stereoselective Synthesis of Benzimidazolinopiperazinone Peptides
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15110%2F14%3A33158892" target="_blank" >RIV/61989592:15110/14:33158892 - isvavai.cz</a>
Result on the web
<a href="http://pubs.acs.org/doi/abs/10.1021/co500023k" target="_blank" >http://pubs.acs.org/doi/abs/10.1021/co500023k</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/co500023k" target="_blank" >10.1021/co500023k</a>
Alternative languages
Result language
angličtina
Original language name
Privileged Structures as Peptide Backbone Constrains: Polymer-Supported Stereoselective Synthesis of Benzimidazolinopiperazinone Peptides
Original language description
A molecular scaffold comprising a privileged structure was designed and synthesized to serve as a peptide backbone conformational constraint. The synthesis of highly functionalized 2,3,10,10 a-tetrahydrobenzoimidazopyrazin-4(1H)-ones on a solid-phase support was performed via a tandem N-acyl-N-aryliminium ion cyclizationMINUS SIGN nucleophilic addition reaction. The synthesis proceeded with full stereocontrol of the newly formed stereogenic center. Conventional and microwave-assisted syntheses were compared with respect to efficiency and the optical integrity of the target compounds. Significant epimerization was observed during acylation with (S)- and (R)-2-bromopropionic acids under microwave conditions.
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
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)
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
ACS Combinatorial Science
ISSN
2156-8952
e-ISSN
—
Volume of the periodical
16
Issue of the periodical within the volume
7
Country of publishing house
US - UNITED STATES
Number of pages
8
Pages from-to
359-366
UT code for WoS article
—
EID of the result in the Scopus database
—