“Cut and Paste” Processes in the Search of Bioactive Products: One-Pot, Metal-free O-Radical Scission-Oxidation-Addition of C, N or P-Nucleophiles
Hypervalent iodine reagents have been applied in many metal-free, efficient synthesis of natural products and other bioactive compounds. In particular, treatment of alcohols, acetals and acids with hypervalent iodine reagents and iodine results in O-radicals that can undergo a β-scission reaction. Under these oxidative conditions, derivatives of amino acids, peptides or carbohydrates are converted into cationic intermediates, which can subsequently undergo inter- or intramolecular addition of nucleophiles. Most reported papers describe the addition of oxygen nucleophiles, but this review is focused on the addition of carbon, nitrogen and phosphorous nucleophiles. The resulting products (nucleoside and alkaloid analogs, unnatural amino acids, site-selectively modified peptides) are valuable intermediates or analogs of bioactive compounds.
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Format: | artículo biblioteca |
Language: | English |
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Frontiers Media
2022-05-18
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Subjects: | Bioactive products, one-pot, metal-free, O-radical, scission-oxidation-addition, C, N, P-nucleophiles, |
Online Access: | http://hdl.handle.net/10261/303069 http://dx.doi.org/10.13039/501100000780 http://dx.doi.org/10.13039/501100004837 |
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dig-ipna-es-10261-3030692023-03-15T02:43:23Z “Cut and Paste” Processes in the Search of Bioactive Products: One-Pot, Metal-free O-Radical Scission-Oxidation-Addition of C, N or P-Nucleophiles Porras, Marina Hernández, Dácil González Martín, Concepción C. Boto, Alicia Ministerio de Ciencia e Innovación (España) European Commission Cabildo de Tenerife Gobierno de Canarias Ministerio de Ciencia, Innovación y Universidades (España) Bioactive products one-pot metal-free O-radical scission-oxidation-addition C, N, P-nucleophiles Hypervalent iodine reagents have been applied in many metal-free, efficient synthesis of natural products and other bioactive compounds. In particular, treatment of alcohols, acetals and acids with hypervalent iodine reagents and iodine results in O-radicals that can undergo a β-scission reaction. Under these oxidative conditions, derivatives of amino acids, peptides or carbohydrates are converted into cationic intermediates, which can subsequently undergo inter- or intramolecular addition of nucleophiles. Most reported papers describe the addition of oxygen nucleophiles, but this review is focused on the addition of carbon, nitrogen and phosphorous nucleophiles. The resulting products (nucleoside and alkaloid analogs, unnatural amino acids, site-selectively modified peptides) are valuable intermediates or analogs of bioactive compounds. This work was partly financed by RETOS project SELECTFIGHT (PID2020-116688RB-C21) from the Spanish Ministry of Science and Innovation (Plan Nacional de I+D) with European Funds for Regional Development-FEDER, and well as by project APOGEO (MAC/1.1.b/226, Cooperation Program INTERREG-MAC 2014‐2020, with European FEDER funds. DH also acknowledges her current contract (TRANSALUDAGRO) financed by Cabildo de Tenerife, Program TF INNOVA 2016-21 (with MEDI & FDCAN Funds). MP thanks predoctoral grants from Gobierno de Canarias (Convocatoria Tesis 2019, REF. TESIS2020010041) and Ministerio de Ciencia, Innovación y Universidades, Spain (FPU grants, REF. FPU19/02589). Peer reviewed 2023-03-14T10:23:20Z 2023-03-14T10:23:20Z 2022-05-18 artículo Frontiers in Chemistry, 10: 1-9 (2022) http://hdl.handle.net/10261/303069 10.3389/fchem.2022.884124 2296-2646 http://dx.doi.org/10.13039/501100000780 http://dx.doi.org/10.13039/501100004837 en #PLACEHOLDER_PARENT_METADATA_VALUE# #PLACEHOLDER_PARENT_METADATA_VALUE# info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2020-116688RB-C21/ES/NUEVOS AGENTES PARA LA LUCHA SELECTIVA CONTRA PATOGENOS: INHIBIDORES DEL QUORUM SENSING Y PEPTIDOS ANTIMICROBIANOS PATOGENO-ESPECIFICOS/ info:eu-repo/grantAgreement/EU/APOGEO/MAC/1.1.b/226 Publisher's version https://doi.org/10.3389/fchem.2022.884124 Sí open Frontiers Media |
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Bioactive products one-pot metal-free O-radical scission-oxidation-addition C, N, P-nucleophiles Bioactive products one-pot metal-free O-radical scission-oxidation-addition C, N, P-nucleophiles |
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Bioactive products one-pot metal-free O-radical scission-oxidation-addition C, N, P-nucleophiles Bioactive products one-pot metal-free O-radical scission-oxidation-addition C, N, P-nucleophiles Porras, Marina Hernández, Dácil González Martín, Concepción C. Boto, Alicia “Cut and Paste” Processes in the Search of Bioactive Products: One-Pot, Metal-free O-Radical Scission-Oxidation-Addition of C, N or P-Nucleophiles |
description |
Hypervalent iodine reagents have been applied in many metal-free, efficient synthesis of natural products and other bioactive compounds. In particular, treatment of alcohols, acetals and acids with hypervalent iodine reagents and iodine results in O-radicals that can undergo a β-scission reaction. Under these oxidative conditions, derivatives of amino acids, peptides or carbohydrates are converted into cationic intermediates, which can subsequently undergo inter- or intramolecular addition of nucleophiles. Most reported papers describe the addition of oxygen nucleophiles, but this review is focused on the addition of carbon, nitrogen and phosphorous nucleophiles. The resulting products (nucleoside and alkaloid analogs, unnatural amino acids, site-selectively modified peptides) are valuable intermediates or analogs of bioactive compounds. |
author2 |
Ministerio de Ciencia e Innovación (España) |
author_facet |
Ministerio de Ciencia e Innovación (España) Porras, Marina Hernández, Dácil González Martín, Concepción C. Boto, Alicia |
format |
artículo |
topic_facet |
Bioactive products one-pot metal-free O-radical scission-oxidation-addition C, N, P-nucleophiles |
author |
Porras, Marina Hernández, Dácil González Martín, Concepción C. Boto, Alicia |
author_sort |
Porras, Marina |
title |
“Cut and Paste” Processes in the Search of Bioactive Products: One-Pot, Metal-free O-Radical Scission-Oxidation-Addition of C, N or P-Nucleophiles |
title_short |
“Cut and Paste” Processes in the Search of Bioactive Products: One-Pot, Metal-free O-Radical Scission-Oxidation-Addition of C, N or P-Nucleophiles |
title_full |
“Cut and Paste” Processes in the Search of Bioactive Products: One-Pot, Metal-free O-Radical Scission-Oxidation-Addition of C, N or P-Nucleophiles |
title_fullStr |
“Cut and Paste” Processes in the Search of Bioactive Products: One-Pot, Metal-free O-Radical Scission-Oxidation-Addition of C, N or P-Nucleophiles |
title_full_unstemmed |
“Cut and Paste” Processes in the Search of Bioactive Products: One-Pot, Metal-free O-Radical Scission-Oxidation-Addition of C, N or P-Nucleophiles |
title_sort |
“cut and paste” processes in the search of bioactive products: one-pot, metal-free o-radical scission-oxidation-addition of c, n or p-nucleophiles |
publisher |
Frontiers Media |
publishDate |
2022-05-18 |
url |
http://hdl.handle.net/10261/303069 http://dx.doi.org/10.13039/501100000780 http://dx.doi.org/10.13039/501100004837 |
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