Polymer-Supported Stereoselective Synthesis of Tetrahydro-2H-oxazolo[3,2-a]pyrazin-5(3H)-ones from N-(2-Oxo-ethyl)-Derivatized Dipeptides via Eastbound Iminiums

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22340%2F13%3A43895073" target="_blank" >RIV/60461373:22340/13:43895073 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.1021/co3001567" target="_blank" >http://dx.doi.org/10.1021/co3001567</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1021/co3001567" target="_blank" >10.1021/co3001567</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Polymer-Supported Stereoselective Synthesis of Tetrahydro-2H-oxazolo[3,2-a]pyrazin-5(3H)-ones from N-(2-Oxo-ethyl)-Derivatized Dipeptides via Eastbound Iminiums

Popis výsledku v původním jazyce

Polymer-supported N-(2-oxo-ethyl)-derivatized Ser/Thr/Cys-containing dipeptides were synthesized and subjected to acid-mediated tandem N-acylium ion cyclization nucleophilic addition to yield tetrahydro-2H-oxazolo-[3,2-a]pyrazin-5(3H)-ones. The reactionconditions and building-block combinations for stereoselective synthesis of the newly formed asymmetric carbon were developed. The synthesis was fay compatible with solid-phase peptide synthesis, and the products serve as conformationally constrained peptidomimetics. The traceless synthesis of bicycles is also reported as part of this work.

Název v anglickém jazyce

Polymer-Supported Stereoselective Synthesis of Tetrahydro-2H-oxazolo[3,2-a]pyrazin-5(3H)-ones from N-(2-Oxo-ethyl)-Derivatized Dipeptides via Eastbound Iminiums

Popis výsledku anglicky

Polymer-supported N-(2-oxo-ethyl)-derivatized Ser/Thr/Cys-containing dipeptides were synthesized and subjected to acid-mediated tandem N-acylium ion cyclization nucleophilic addition to yield tetrahydro-2H-oxazolo-[3,2-a]pyrazin-5(3H)-ones. The reactionconditions and building-block combinations for stereoselective synthesis of the newly formed asymmetric carbon were developed. The synthesis was fay compatible with solid-phase peptide synthesis, and the products serve as conformationally constrained peptidomimetics. The traceless synthesis of bicycles is also reported as part of this work.

Druh

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

CEP obor

FR - Farmakologie a lékárnická chemie

OECD FORD obor

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Projekt

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Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2013

Kód důvěrnosti údajů

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

Název periodika

ACS Combinatorial Science

ISSN

2156-8952

e-ISSN

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Svazek periodika

15

Číslo periodika v rámci svazku

3

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

6

Strana od-do

162-167

Kód UT WoS článku

000316044900004

EID výsledku v databázi Scopus

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