The Experts below are selected from a list of 312 Experts worldwide ranked by ideXlab platform
Sara Pellegrino - One of the best experts on this subject based on the ideXlab platform.
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on resin multicomponent 1 3 dipolar cycloaddition of cyclopentanone proline enamines and sulfonylazides as an efficient tool for the synthesis of amidino depsipeptide mimics
Amino Acids, 2020Co-Authors: Raffaella Bucci, Federico Dapiaggi, Helena Macut, Stefano Pieraccini, Emanuela Erba, Maria Luisa Gelmi, Maurizio Sironi, Sara PellegrinoAbstract:Depsipeptides are biologically active peptide derivatives that possess a high therapeutic interest. The development of depsipeptide mimics characterized by a chemical diversity could lead to compounds with enhanced features and activity. In this work, an on-resin multicomponent procedure for the synthesis of amidino depsipeptide mimics is described. This approach exploits a metal-free 1,3-dipolar cycloaddition of cyclopentanone–proline enamines and sulfonylazides. In this reaction, the obtained primary cycloadduct undergoes a ring opening and molecular rearrangement giving access to a linear sulfonyl amidine functionalized with both a peptide chain and a diazoalkane. The so-obtained diazo function “one pot” reacts with the carboxylic group of N-Fmoc-protected amino acids leading to amidino depsipeptide mimics possessing a C4 aliphatic chain. An important advantage of this procedure is the possibility to easily obtain amidino-functionalized derivatives that are proteolytically stable peptide bond bioisosteres. Moreover, the conformational freedom given by the alkyl chain could promote the obtainment of cyclic depsipeptide with a stabilized secondary structure as demonstrated with both in silico calculations and experimental conformational studies. Finally, labeled depsipeptide mimics can be also synthesized using a fluorescent sulfonylazide in the multicomponent reaction.
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On-resin multicomponent 1,3-dipolar cycloaddition of cyclopentanone–proline enamines and sulfonylazides as an efficient tool for the synthesis of amidino depsipeptide mimics
Amino Acids, 2019Co-Authors: Raffaella Bucci, Federico Dapiaggi, Helena Macut, Stefano Pieraccini, Emanuela Erba, Maria Luisa Gelmi, Maurizio Sironi, Sara PellegrinoAbstract:Depsipeptides are biologically active peptide derivatives that possess a high therapeutic interest. The development of depsipeptide mimics characterized by a chemical diversity could lead to compounds with enhanced features and activity. In this work, an on-resin multicomponent procedure for the synthesis of amidino depsipeptide mimics is described. This approach exploits a metal-free 1,3-dipolar cycloaddition of cyclopentanone–proline enamines and sulfonylazides. In this reaction, the obtained primary cycloadduct undergoes a ring opening and molecular rearrangement giving access to a linear sulfonyl amidine functionalized with both a peptide chain and a diazoalkane. The so-obtained diazo function “one pot” reacts with the carboxylic group of N -Fmoc-protected amino acids leading to amidino depsipeptide mimics possessing a C4 aliphatic chain. An important advantage of this procedure is the possibility to easily obtain amidino-functionalized derivatives that are proteolytically stable peptide bond bioisosteres. Moreover, the conformational freedom given by the alkyl chain could promote the obtainment of cyclic depsipeptide with a stabilized secondary structure as demonstrated with both in silico calculations and experimental conformational studies. Finally, labeled depsipeptide mimics can be also synthesized using a fluorescent sulfonylazide in the multicomponent reaction.
Valentine G. Nenajdenko - One of the best experts on this subject based on the ideXlab platform.
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the passerini reaction with cf3 carbonyl compounds multicomponent approach to trifluoromethyl Depsipeptides
ChemInform, 2009Co-Authors: Anton V Gulevich, Inga V. Shpilevaya, Valentine G. NenajdenkoAbstract:The first detailed investigation of the Paserini reaction with CF3-carbonyl compounds is reported. The reaction provides a new approach to trifluorolactic acid derivatives and CF3-substituted Depsipeptides. The method is promising for the synthesis of chiral trifluoromethyl Depsipeptides, i.e. orthogonally protected building blocks for incorporation into naturally occurring Depsipeptides.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
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The Passerini Reaction with CF3-Carbonyl Compounds – Multicomponent Approach to Trifluoromethyl Depsipeptides
European Journal of Organic Chemistry, 2009Co-Authors: Anton V Gulevich, Inga V. Shpilevaya, Valentine G. NenajdenkoAbstract:The first detailed investigation of the Paserini reaction with CF3-carbonyl compounds is reported. The reaction provides a new approach to trifluorolactic acid derivatives and CF3-substituted Depsipeptides. The method is promising for the synthesis of chiral trifluoromethyl Depsipeptides, i.e. orthogonally protected building blocks for incorporation into naturally occurring Depsipeptides.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
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The Passerini Reaction with CF3‐Carbonyl Compounds – Multicomponent Approach to Trifluoromethyl Depsipeptides
European Journal of Organic Chemistry, 2009Co-Authors: Anton V Gulevich, Inga V. Shpilevaya, Valentine G. NenajdenkoAbstract:The first detailed investigation of the Paserini reaction with CF3-carbonyl compounds is reported. The reaction provides a new approach to trifluorolactic acid derivatives and CF3-substituted Depsipeptides. The method is promising for the synthesis of chiral trifluoromethyl Depsipeptides, i.e. orthogonally protected building blocks for incorporation into naturally occurring Depsipeptides.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
Raffaella Bucci - One of the best experts on this subject based on the ideXlab platform.
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on resin multicomponent 1 3 dipolar cycloaddition of cyclopentanone proline enamines and sulfonylazides as an efficient tool for the synthesis of amidino depsipeptide mimics
Amino Acids, 2020Co-Authors: Raffaella Bucci, Federico Dapiaggi, Helena Macut, Stefano Pieraccini, Emanuela Erba, Maria Luisa Gelmi, Maurizio Sironi, Sara PellegrinoAbstract:Depsipeptides are biologically active peptide derivatives that possess a high therapeutic interest. The development of depsipeptide mimics characterized by a chemical diversity could lead to compounds with enhanced features and activity. In this work, an on-resin multicomponent procedure for the synthesis of amidino depsipeptide mimics is described. This approach exploits a metal-free 1,3-dipolar cycloaddition of cyclopentanone–proline enamines and sulfonylazides. In this reaction, the obtained primary cycloadduct undergoes a ring opening and molecular rearrangement giving access to a linear sulfonyl amidine functionalized with both a peptide chain and a diazoalkane. The so-obtained diazo function “one pot” reacts with the carboxylic group of N-Fmoc-protected amino acids leading to amidino depsipeptide mimics possessing a C4 aliphatic chain. An important advantage of this procedure is the possibility to easily obtain amidino-functionalized derivatives that are proteolytically stable peptide bond bioisosteres. Moreover, the conformational freedom given by the alkyl chain could promote the obtainment of cyclic depsipeptide with a stabilized secondary structure as demonstrated with both in silico calculations and experimental conformational studies. Finally, labeled depsipeptide mimics can be also synthesized using a fluorescent sulfonylazide in the multicomponent reaction.
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On-resin multicomponent 1,3-dipolar cycloaddition of cyclopentanone–proline enamines and sulfonylazides as an efficient tool for the synthesis of amidino depsipeptide mimics
Amino Acids, 2019Co-Authors: Raffaella Bucci, Federico Dapiaggi, Helena Macut, Stefano Pieraccini, Emanuela Erba, Maria Luisa Gelmi, Maurizio Sironi, Sara PellegrinoAbstract:Depsipeptides are biologically active peptide derivatives that possess a high therapeutic interest. The development of depsipeptide mimics characterized by a chemical diversity could lead to compounds with enhanced features and activity. In this work, an on-resin multicomponent procedure for the synthesis of amidino depsipeptide mimics is described. This approach exploits a metal-free 1,3-dipolar cycloaddition of cyclopentanone–proline enamines and sulfonylazides. In this reaction, the obtained primary cycloadduct undergoes a ring opening and molecular rearrangement giving access to a linear sulfonyl amidine functionalized with both a peptide chain and a diazoalkane. The so-obtained diazo function “one pot” reacts with the carboxylic group of N -Fmoc-protected amino acids leading to amidino depsipeptide mimics possessing a C4 aliphatic chain. An important advantage of this procedure is the possibility to easily obtain amidino-functionalized derivatives that are proteolytically stable peptide bond bioisosteres. Moreover, the conformational freedom given by the alkyl chain could promote the obtainment of cyclic depsipeptide with a stabilized secondary structure as demonstrated with both in silico calculations and experimental conformational studies. Finally, labeled depsipeptide mimics can be also synthesized using a fluorescent sulfonylazide in the multicomponent reaction.
Anton V Gulevich - One of the best experts on this subject based on the ideXlab platform.
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the passerini reaction with cf3 carbonyl compounds multicomponent approach to trifluoromethyl Depsipeptides
ChemInform, 2009Co-Authors: Anton V Gulevich, Inga V. Shpilevaya, Valentine G. NenajdenkoAbstract:The first detailed investigation of the Paserini reaction with CF3-carbonyl compounds is reported. The reaction provides a new approach to trifluorolactic acid derivatives and CF3-substituted Depsipeptides. The method is promising for the synthesis of chiral trifluoromethyl Depsipeptides, i.e. orthogonally protected building blocks for incorporation into naturally occurring Depsipeptides.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
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The Passerini Reaction with CF3-Carbonyl Compounds – Multicomponent Approach to Trifluoromethyl Depsipeptides
European Journal of Organic Chemistry, 2009Co-Authors: Anton V Gulevich, Inga V. Shpilevaya, Valentine G. NenajdenkoAbstract:The first detailed investigation of the Paserini reaction with CF3-carbonyl compounds is reported. The reaction provides a new approach to trifluorolactic acid derivatives and CF3-substituted Depsipeptides. The method is promising for the synthesis of chiral trifluoromethyl Depsipeptides, i.e. orthogonally protected building blocks for incorporation into naturally occurring Depsipeptides.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
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The Passerini Reaction with CF3‐Carbonyl Compounds – Multicomponent Approach to Trifluoromethyl Depsipeptides
European Journal of Organic Chemistry, 2009Co-Authors: Anton V Gulevich, Inga V. Shpilevaya, Valentine G. NenajdenkoAbstract:The first detailed investigation of the Paserini reaction with CF3-carbonyl compounds is reported. The reaction provides a new approach to trifluorolactic acid derivatives and CF3-substituted Depsipeptides. The method is promising for the synthesis of chiral trifluoromethyl Depsipeptides, i.e. orthogonally protected building blocks for incorporation into naturally occurring Depsipeptides.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
Emanuela Erba - One of the best experts on this subject based on the ideXlab platform.
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on resin multicomponent 1 3 dipolar cycloaddition of cyclopentanone proline enamines and sulfonylazides as an efficient tool for the synthesis of amidino depsipeptide mimics
Amino Acids, 2020Co-Authors: Raffaella Bucci, Federico Dapiaggi, Helena Macut, Stefano Pieraccini, Emanuela Erba, Maria Luisa Gelmi, Maurizio Sironi, Sara PellegrinoAbstract:Depsipeptides are biologically active peptide derivatives that possess a high therapeutic interest. The development of depsipeptide mimics characterized by a chemical diversity could lead to compounds with enhanced features and activity. In this work, an on-resin multicomponent procedure for the synthesis of amidino depsipeptide mimics is described. This approach exploits a metal-free 1,3-dipolar cycloaddition of cyclopentanone–proline enamines and sulfonylazides. In this reaction, the obtained primary cycloadduct undergoes a ring opening and molecular rearrangement giving access to a linear sulfonyl amidine functionalized with both a peptide chain and a diazoalkane. The so-obtained diazo function “one pot” reacts with the carboxylic group of N-Fmoc-protected amino acids leading to amidino depsipeptide mimics possessing a C4 aliphatic chain. An important advantage of this procedure is the possibility to easily obtain amidino-functionalized derivatives that are proteolytically stable peptide bond bioisosteres. Moreover, the conformational freedom given by the alkyl chain could promote the obtainment of cyclic depsipeptide with a stabilized secondary structure as demonstrated with both in silico calculations and experimental conformational studies. Finally, labeled depsipeptide mimics can be also synthesized using a fluorescent sulfonylazide in the multicomponent reaction.
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On-resin multicomponent 1,3-dipolar cycloaddition of cyclopentanone–proline enamines and sulfonylazides as an efficient tool for the synthesis of amidino depsipeptide mimics
Amino Acids, 2019Co-Authors: Raffaella Bucci, Federico Dapiaggi, Helena Macut, Stefano Pieraccini, Emanuela Erba, Maria Luisa Gelmi, Maurizio Sironi, Sara PellegrinoAbstract:Depsipeptides are biologically active peptide derivatives that possess a high therapeutic interest. The development of depsipeptide mimics characterized by a chemical diversity could lead to compounds with enhanced features and activity. In this work, an on-resin multicomponent procedure for the synthesis of amidino depsipeptide mimics is described. This approach exploits a metal-free 1,3-dipolar cycloaddition of cyclopentanone–proline enamines and sulfonylazides. In this reaction, the obtained primary cycloadduct undergoes a ring opening and molecular rearrangement giving access to a linear sulfonyl amidine functionalized with both a peptide chain and a diazoalkane. The so-obtained diazo function “one pot” reacts with the carboxylic group of N -Fmoc-protected amino acids leading to amidino depsipeptide mimics possessing a C4 aliphatic chain. An important advantage of this procedure is the possibility to easily obtain amidino-functionalized derivatives that are proteolytically stable peptide bond bioisosteres. Moreover, the conformational freedom given by the alkyl chain could promote the obtainment of cyclic depsipeptide with a stabilized secondary structure as demonstrated with both in silico calculations and experimental conformational studies. Finally, labeled depsipeptide mimics can be also synthesized using a fluorescent sulfonylazide in the multicomponent reaction.