Non-natural 3-Arylmorpholino-β-amino Acid as a PPII Helix Inducer

[Image: see text] A new non-natural β-amino acid, named 3-Ar-β-Morph, was designed and synthesized via a regio- and diastereoselective Pd-catalyzed C(sp(3))H-arylation of the corresponding 2S,6S-(6-methoxymorpholin-2-yl)carboxylic acid, readily available from glucose. According to the computational...

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Autores principales: Vaghi, Francesco, Bucci, Raffaella, Clerici, Francesca, Contini, Alessandro, Gelmi, M. Luisa
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8009597/
https://www.ncbi.nlm.nih.gov/pubmed/32790435
http://dx.doi.org/10.1021/acs.orglett.0c02331
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author Vaghi, Francesco
Bucci, Raffaella
Clerici, Francesca
Contini, Alessandro
Gelmi, M. Luisa
author_facet Vaghi, Francesco
Bucci, Raffaella
Clerici, Francesca
Contini, Alessandro
Gelmi, M. Luisa
author_sort Vaghi, Francesco
collection PubMed
description [Image: see text] A new non-natural β-amino acid, named 3-Ar-β-Morph, was designed and synthesized via a regio- and diastereoselective Pd-catalyzed C(sp(3))H-arylation of the corresponding 2S,6S-(6-methoxymorpholin-2-yl)carboxylic acid, readily available from glucose. According to the computational prevision and confirmed by IR and NMR data, the insertion of 3-Ar-β-Morph in a model foldamer represents a way to stabilize a PPII-like helix through the presence of two γ-turns, secondary structure motifs induced by the morpholine ring, and the trans-tertiary amide bond.
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spelling pubmed-80095972021-03-31 Non-natural 3-Arylmorpholino-β-amino Acid as a PPII Helix Inducer Vaghi, Francesco Bucci, Raffaella Clerici, Francesca Contini, Alessandro Gelmi, M. Luisa Org Lett [Image: see text] A new non-natural β-amino acid, named 3-Ar-β-Morph, was designed and synthesized via a regio- and diastereoselective Pd-catalyzed C(sp(3))H-arylation of the corresponding 2S,6S-(6-methoxymorpholin-2-yl)carboxylic acid, readily available from glucose. According to the computational prevision and confirmed by IR and NMR data, the insertion of 3-Ar-β-Morph in a model foldamer represents a way to stabilize a PPII-like helix through the presence of two γ-turns, secondary structure motifs induced by the morpholine ring, and the trans-tertiary amide bond. American Chemical Society 2020-07-30 2020-08-07 /pmc/articles/PMC8009597/ /pubmed/32790435 http://dx.doi.org/10.1021/acs.orglett.0c02331 Text en Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Vaghi, Francesco
Bucci, Raffaella
Clerici, Francesca
Contini, Alessandro
Gelmi, M. Luisa
Non-natural 3-Arylmorpholino-β-amino Acid as a PPII Helix Inducer
title Non-natural 3-Arylmorpholino-β-amino Acid as a PPII Helix Inducer
title_full Non-natural 3-Arylmorpholino-β-amino Acid as a PPII Helix Inducer
title_fullStr Non-natural 3-Arylmorpholino-β-amino Acid as a PPII Helix Inducer
title_full_unstemmed Non-natural 3-Arylmorpholino-β-amino Acid as a PPII Helix Inducer
title_short Non-natural 3-Arylmorpholino-β-amino Acid as a PPII Helix Inducer
title_sort non-natural 3-arylmorpholino-β-amino acid as a ppii helix inducer
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8009597/
https://www.ncbi.nlm.nih.gov/pubmed/32790435
http://dx.doi.org/10.1021/acs.orglett.0c02331
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