New Morphiceptin Peptidomimetic Incorporating (1S,2R,3S,4S,5R)-2-Amino-3,4,5-trihydroxycyclopen-tane-1-carboxylic acid: Synthesis and Structural Study

We present the synthesis and structural study of a new peptidomimetic of morphiceptin, which can formally be considered as the result of the replacement of the central proline residue of this natural analgesic drug with a subunit of (1S,2R,3S,4S,5R)-2-amino-3,4,5-trihydroxycyclopentane-1-carboxylic...

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Autores principales: Soengas, Raquel, Lorca, Marcos, Pampín, Begoña, Sánchez-Pedregal, Víctor M., Estévez, Ramón J., Estévez, Juan C.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
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Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7321350/
https://www.ncbi.nlm.nih.gov/pubmed/32492956
http://dx.doi.org/10.3390/molecules25112574
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author Soengas, Raquel
Lorca, Marcos
Pampín, Begoña
Sánchez-Pedregal, Víctor M.
Estévez, Ramón J.
Estévez, Juan C.
author_facet Soengas, Raquel
Lorca, Marcos
Pampín, Begoña
Sánchez-Pedregal, Víctor M.
Estévez, Ramón J.
Estévez, Juan C.
author_sort Soengas, Raquel
collection PubMed
description We present the synthesis and structural study of a new peptidomimetic of morphiceptin, which can formally be considered as the result of the replacement of the central proline residue of this natural analgesic drug with a subunit of (1S,2R,3S,4S,5R)-2-amino-3,4,5-trihydroxycyclopentane-1-carboxylic acid, previously obtained from L-idose. An optimized synthesis of this trihydroxylated cispentacin derivative is also reported. Molecular docking calculations on the target receptor support a favorable role of the hydroxy substituents of the non-natural β-amino acid incorporated into the peptidomimetic.
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spelling pubmed-73213502020-06-29 New Morphiceptin Peptidomimetic Incorporating (1S,2R,3S,4S,5R)-2-Amino-3,4,5-trihydroxycyclopen-tane-1-carboxylic acid: Synthesis and Structural Study Soengas, Raquel Lorca, Marcos Pampín, Begoña Sánchez-Pedregal, Víctor M. Estévez, Ramón J. Estévez, Juan C. Molecules Article We present the synthesis and structural study of a new peptidomimetic of morphiceptin, which can formally be considered as the result of the replacement of the central proline residue of this natural analgesic drug with a subunit of (1S,2R,3S,4S,5R)-2-amino-3,4,5-trihydroxycyclopentane-1-carboxylic acid, previously obtained from L-idose. An optimized synthesis of this trihydroxylated cispentacin derivative is also reported. Molecular docking calculations on the target receptor support a favorable role of the hydroxy substituents of the non-natural β-amino acid incorporated into the peptidomimetic. MDPI 2020-06-01 /pmc/articles/PMC7321350/ /pubmed/32492956 http://dx.doi.org/10.3390/molecules25112574 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Soengas, Raquel
Lorca, Marcos
Pampín, Begoña
Sánchez-Pedregal, Víctor M.
Estévez, Ramón J.
Estévez, Juan C.
New Morphiceptin Peptidomimetic Incorporating (1S,2R,3S,4S,5R)-2-Amino-3,4,5-trihydroxycyclopen-tane-1-carboxylic acid: Synthesis and Structural Study
title New Morphiceptin Peptidomimetic Incorporating (1S,2R,3S,4S,5R)-2-Amino-3,4,5-trihydroxycyclopen-tane-1-carboxylic acid: Synthesis and Structural Study
title_full New Morphiceptin Peptidomimetic Incorporating (1S,2R,3S,4S,5R)-2-Amino-3,4,5-trihydroxycyclopen-tane-1-carboxylic acid: Synthesis and Structural Study
title_fullStr New Morphiceptin Peptidomimetic Incorporating (1S,2R,3S,4S,5R)-2-Amino-3,4,5-trihydroxycyclopen-tane-1-carboxylic acid: Synthesis and Structural Study
title_full_unstemmed New Morphiceptin Peptidomimetic Incorporating (1S,2R,3S,4S,5R)-2-Amino-3,4,5-trihydroxycyclopen-tane-1-carboxylic acid: Synthesis and Structural Study
title_short New Morphiceptin Peptidomimetic Incorporating (1S,2R,3S,4S,5R)-2-Amino-3,4,5-trihydroxycyclopen-tane-1-carboxylic acid: Synthesis and Structural Study
title_sort new morphiceptin peptidomimetic incorporating (1s,2r,3s,4s,5r)-2-amino-3,4,5-trihydroxycyclopen-tane-1-carboxylic acid: synthesis and structural study
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7321350/
https://www.ncbi.nlm.nih.gov/pubmed/32492956
http://dx.doi.org/10.3390/molecules25112574
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