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

The result's identifiers

  • Result code in 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>

  • Alternative codes found

    RIV/00216208:11310/22:10454367

  • Result on the web

    <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>

Alternative languages

  • Result language

    angličtina

  • Original language name

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

  • Original language description

    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.

  • Czech name

  • Czech description

Classification

  • Type

    J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database

  • CEP classification

  • OECD FORD branch

    10401 - Organic chemistry

Result continuities

  • Project

    <a href="/en/project/EF16_019%2F0000729" target="_blank" >EF16_019/0000729: Chemical biology for drugging undruggable targets</a><br>

  • Continuities

    I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Others

  • Publication year

    2022

  • Confidentiality

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

Data specific for result type

  • Name of the periodical

    Advanced Synthesis & Catalysis

  • ISSN

    1615-4150

  • e-ISSN

    1615-4169

  • Volume of the periodical

    364

  • Issue of the periodical within the volume

    2

  • Country of publishing house

    DE - GERMANY

  • Number of pages

    8

  • Pages from-to

    405-412

  • UT code for WoS article

    000711550100001

  • EID of the result in the Scopus database

    2-s2.0-85118209220