Sulfur-Switch Ugi Reaction for Macrocyclic Disulfide-Bridged Peptidomimetics

[Image: see text] A general strategy is introduced for the efficient synthetic access of disulfide linked artificial macrocycles via a Ugi four-component reaction (U4CR) followed by oxidative cyclization. The double-mercapto input is proposed for use in the Ugi reaction, thereby yielding all six top...

Descripción completa

Detalles Bibliográficos
Autores principales: Vishwanatha, Thimmalapura M., Bergamaschi, Enrico, Dömling, Alexander
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5477004/
https://www.ncbi.nlm.nih.gov/pubmed/28581763
http://dx.doi.org/10.1021/acs.orglett.7b01324
_version_ 1783244702925979648
author Vishwanatha, Thimmalapura M.
Bergamaschi, Enrico
Dömling, Alexander
author_facet Vishwanatha, Thimmalapura M.
Bergamaschi, Enrico
Dömling, Alexander
author_sort Vishwanatha, Thimmalapura M.
collection PubMed
description [Image: see text] A general strategy is introduced for the efficient synthetic access of disulfide linked artificial macrocycles via a Ugi four-component reaction (U4CR) followed by oxidative cyclization. The double-mercapto input is proposed for use in the Ugi reaction, thereby yielding all six topologically possible combinations. The protocol is convergent and short and enables the production of novel disulfide peptidomimetics in a highly general fashion.
format Online
Article
Text
id pubmed-5477004
institution National Center for Biotechnology Information
language English
publishDate 2017
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-54770042017-06-21 Sulfur-Switch Ugi Reaction for Macrocyclic Disulfide-Bridged Peptidomimetics Vishwanatha, Thimmalapura M. Bergamaschi, Enrico Dömling, Alexander Org Lett [Image: see text] A general strategy is introduced for the efficient synthetic access of disulfide linked artificial macrocycles via a Ugi four-component reaction (U4CR) followed by oxidative cyclization. The double-mercapto input is proposed for use in the Ugi reaction, thereby yielding all six topologically possible combinations. The protocol is convergent and short and enables the production of novel disulfide peptidomimetics in a highly general fashion. American Chemical Society 2017-06-05 2017-06-16 /pmc/articles/PMC5477004/ /pubmed/28581763 http://dx.doi.org/10.1021/acs.orglett.7b01324 Text en Copyright © 2017 American Chemical Society This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License (http://pubs.acs.org/page/policy/authorchoice_ccbyncnd_termsofuse.html) , which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes.
spellingShingle Vishwanatha, Thimmalapura M.
Bergamaschi, Enrico
Dömling, Alexander
Sulfur-Switch Ugi Reaction for Macrocyclic Disulfide-Bridged Peptidomimetics
title Sulfur-Switch Ugi Reaction for Macrocyclic Disulfide-Bridged Peptidomimetics
title_full Sulfur-Switch Ugi Reaction for Macrocyclic Disulfide-Bridged Peptidomimetics
title_fullStr Sulfur-Switch Ugi Reaction for Macrocyclic Disulfide-Bridged Peptidomimetics
title_full_unstemmed Sulfur-Switch Ugi Reaction for Macrocyclic Disulfide-Bridged Peptidomimetics
title_short Sulfur-Switch Ugi Reaction for Macrocyclic Disulfide-Bridged Peptidomimetics
title_sort sulfur-switch ugi reaction for macrocyclic disulfide-bridged peptidomimetics
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5477004/
https://www.ncbi.nlm.nih.gov/pubmed/28581763
http://dx.doi.org/10.1021/acs.orglett.7b01324
work_keys_str_mv AT vishwanathathimmalapuram sulfurswitchugireactionformacrocyclicdisulfidebridgedpeptidomimetics
AT bergamaschienrico sulfurswitchugireactionformacrocyclicdisulfidebridgedpeptidomimetics
AT domlingalexander sulfurswitchugireactionformacrocyclicdisulfidebridgedpeptidomimetics

Ejemplares similares