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Polyhydroxylated Cyclopentane β-Amino Acids Derived from d-Mannose and d-Galactose: Synthesis and Protocol for Incorporation into Peptides
[Image: see text] A stereoselective synthesis of polyhydroxylated cyclopentane β-amino acids from hexoses is reported. The reaction sequence comprises, as key steps, ring-closing metathesis of a polysubstituted diene intermediate followed by the stereoselective aza-Michael functionalization of the r...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2022
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8772316/ https://www.ncbi.nlm.nih.gov/pubmed/35071888 http://dx.doi.org/10.1021/acsomega.1c05468 |
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author | Fernández, Fernando Fernández, Alberto G. Balo, Rosalino Sánchez-Pedregal, Víctor M. Royo, Miriam Soengas, Raquel G. Estévez, Ramón J. Estévez, Juan C. |
author_facet | Fernández, Fernando Fernández, Alberto G. Balo, Rosalino Sánchez-Pedregal, Víctor M. Royo, Miriam Soengas, Raquel G. Estévez, Ramón J. Estévez, Juan C. |
author_sort | Fernández, Fernando |
collection | PubMed |
description | [Image: see text] A stereoselective synthesis of polyhydroxylated cyclopentane β-amino acids from hexoses is reported. The reaction sequence comprises, as key steps, ring-closing metathesis of a polysubstituted diene intermediate followed by the stereoselective aza-Michael functionalization of the resulting cyclopent-1-ene-1-carboxylic acid ester. Examples of synthesis of polysubstituted 2-aminocyclopentanecarboxylic acid derivatives starting from protected d-mannose and d-galactose are presented. A general protocol for the incorporation of these highly functionalized alicyclic β-amino acids into peptides is also reported. |
format | Online Article Text |
id | pubmed-8772316 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-87723162022-01-21 Polyhydroxylated Cyclopentane β-Amino Acids Derived from d-Mannose and d-Galactose: Synthesis and Protocol for Incorporation into Peptides Fernández, Fernando Fernández, Alberto G. Balo, Rosalino Sánchez-Pedregal, Víctor M. Royo, Miriam Soengas, Raquel G. Estévez, Ramón J. Estévez, Juan C. ACS Omega [Image: see text] A stereoselective synthesis of polyhydroxylated cyclopentane β-amino acids from hexoses is reported. The reaction sequence comprises, as key steps, ring-closing metathesis of a polysubstituted diene intermediate followed by the stereoselective aza-Michael functionalization of the resulting cyclopent-1-ene-1-carboxylic acid ester. Examples of synthesis of polysubstituted 2-aminocyclopentanecarboxylic acid derivatives starting from protected d-mannose and d-galactose are presented. A general protocol for the incorporation of these highly functionalized alicyclic β-amino acids into peptides is also reported. American Chemical Society 2022-01-04 /pmc/articles/PMC8772316/ /pubmed/35071888 http://dx.doi.org/10.1021/acsomega.1c05468 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/). |
spellingShingle | Fernández, Fernando Fernández, Alberto G. Balo, Rosalino Sánchez-Pedregal, Víctor M. Royo, Miriam Soengas, Raquel G. Estévez, Ramón J. Estévez, Juan C. Polyhydroxylated Cyclopentane β-Amino Acids Derived from d-Mannose and d-Galactose: Synthesis and Protocol for Incorporation into Peptides |
title | Polyhydroxylated Cyclopentane β-Amino
Acids Derived from d-Mannose and d-Galactose:
Synthesis and Protocol for Incorporation into Peptides |
title_full | Polyhydroxylated Cyclopentane β-Amino
Acids Derived from d-Mannose and d-Galactose:
Synthesis and Protocol for Incorporation into Peptides |
title_fullStr | Polyhydroxylated Cyclopentane β-Amino
Acids Derived from d-Mannose and d-Galactose:
Synthesis and Protocol for Incorporation into Peptides |
title_full_unstemmed | Polyhydroxylated Cyclopentane β-Amino
Acids Derived from d-Mannose and d-Galactose:
Synthesis and Protocol for Incorporation into Peptides |
title_short | Polyhydroxylated Cyclopentane β-Amino
Acids Derived from d-Mannose and d-Galactose:
Synthesis and Protocol for Incorporation into Peptides |
title_sort | polyhydroxylated cyclopentane β-amino
acids derived from d-mannose and d-galactose:
synthesis and protocol for incorporation into peptides |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8772316/ https://www.ncbi.nlm.nih.gov/pubmed/35071888 http://dx.doi.org/10.1021/acsomega.1c05468 |
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