Single Electron Transfer-Induced Selective α-Oxygenation of Glycine Derivatives

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F22%3A00551919" target="_blank" >RIV/61388963:_____/22:00551919 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/00216208:11310/22:10454367

Výsledek na webu

<a href="https://doi.org/10.1002/adsc.202100964" target="_blank" >https://doi.org/10.1002/adsc.202100964</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/adsc.202100964" target="_blank" >10.1002/adsc.202100964</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Single Electron Transfer-Induced Selective α-Oxygenation of Glycine Derivatives

Popis výsledku v původním jazyce

Modification of amino acids is an important strategy in organic and bioorganic chemistry. In contrast to common side-chain functionalization, backbone modification is much less explored. Especially glycine units seem to be attractive and versatile since a wide range of functionality can be potentially introduced. We report here oxidative modification of glycinates that are stable and enable further functionalization. Selective glycinate enolate oxidation by TEMPO or a FeCp2PF6/TEMPO reagent combination provides stable alkoxyamines in good to excellent yields. The methodology is expanded to glycine-containing dipeptides demonstrating selective oxygenation at the glycine unit. The orthogonal reactivity potential of oxygenated glycines for transformation to other amino acid derivatives is explored.

Název v anglickém jazyce

Single Electron Transfer-Induced Selective α-Oxygenation of Glycine Derivatives

Popis výsledku anglicky

Modification of amino acids is an important strategy in organic and bioorganic chemistry. In contrast to common side-chain functionalization, backbone modification is much less explored. Especially glycine units seem to be attractive and versatile since a wide range of functionality can be potentially introduced. We report here oxidative modification of glycinates that are stable and enable further functionalization. Selective glycinate enolate oxidation by TEMPO or a FeCp2PF6/TEMPO reagent combination provides stable alkoxyamines in good to excellent yields. The methodology is expanded to glycine-containing dipeptides demonstrating selective oxygenation at the glycine unit. The orthogonal reactivity potential of oxygenated glycines for transformation to other amino acid derivatives is explored.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/EF16_019%2F0000729" target="_blank" >EF16_019/0000729: Chemická biologie pro vývoj nových terapií</a><br>

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2022

Kód důvěrnosti údajů

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

Název periodika

Advanced Synthesis & Catalysis

ISSN

1615-4150

e-ISSN

1615-4169

Svazek periodika

364

Číslo periodika v rámci svazku

2

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

8

Strana od-do

405-412

Kód UT WoS článku

000711550100001

EID výsledku v databázi Scopus

2-s2.0-85118209220