Peptide‐Hypervalent Iodine Reagent Chimeras: Enabling Peptide Functionalization and Macrocyclization **
Abstract: Herein, we report a novel strategy for the modification of peptides based on the introduction of highly reactive hypervalent iodine reagents—ethynylbenziodoxolones (EBXs)—onto peptides. These peptide‐EBXs can be readily accessed, by both solution‐ and solid‐phase peptide synthesis (SPPS). They can be used to couple the peptide to other peptides or a protein through reaction with Cys, leading to thioalkynes in organic solvents and hypervalent iodine adducts in water buffer. Furthermore, a photocatalytic decarboxylative coupling to the C‐terminus of peptides was developed using an organic dye and was also successful in an intramolecular fashion, leading to macrocyclic peptides with unprecedented crosslinking. A rigid linear aryl alkyne linker was essential to achieve high affinity for Keap1 at the Nrf2 binding site with potential protein‐protein interaction inhibition.
- Standort
-
Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
-
Online-Ressource
- Sprache
-
Englisch
- Erschienen in
-
Peptide‐Hypervalent Iodine Reagent Chimeras: Enabling Peptide Functionalization and Macrocyclization ** ; day:07 ; month:07 ; year:2023 ; extent:11
Angewandte Chemie / International edition. International edition ; (07.07.2023) (gesamt 11)
- Urheber
-
Liu, Xing‐Yu
Ji, Xinjian
Heinis, Christian
Waser, Jerome
- DOI
-
10.1002/anie.202306036
- URN
-
urn:nbn:de:101:1-2023070815391506993635
- Rechteinformation
-
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
-
14.08.2025, 10:44 MESZ
Datenpartner
Dieses Objekt wird bereitgestellt von:
Deutsche Nationalbibliothek. Bei Fragen zum Objekt wenden Sie sich bitte an den Datenpartner.
Deutsche Nationalbibliothek. Bei Fragen zum Objekt wenden Sie sich bitte an den Datenpartner.
Beteiligte
- Liu, Xing‐Yu
- Ji, Xinjian
- Heinis, Christian
- Waser, Jerome
Ähnliche Objekte (12)
Peptide‐Hypervalent Iodine Reagent Chimeras: Enabling Peptide Functionalization and Macrocyclization **
Togni Reagent: A Hypervalent Iodine Based Electrophilic Trifluoromethylation Reagent
Recyclable hypervalent-iodine-mediated solid-phase peptide synthesis and cyclic peptide synthesis
Hypervalent Iodine‐Mediated Late‐Stage Peptide and Protein Functionalization
Hypervalent Iodine‐Mediated Late‐Stage Peptide and Protein Functionalization
Hypervalent Iodine Amino Acid Building Blocks for Bioorthogonal Peptide Macrocyclization
Hypervalent Iodine Amino Acid Building Blocks for Bioorthogonal Peptide Macrocyclization
A Fluorinating Hypervalent Iodine(III) Reagent: 4-Iodotoluene Difluoride
Phosphate-Reagent-Mediated Peptide Coupling Reactions
Rapid transformation of sulfinate salts into sulfonates promoted by a hypervalent iodine(III) reagent
Solvent-dependent chemoselective synthesis of different isoquinolinones mediated by the hypervalent iodine(III) reagent PISA
Hypervalent Iodine for α,α-Dihalogenation
Peptide‐Hypervalent Iodine Reagent Chimeras: Enabling Peptide Functionalization and Macrocyclization **
Togni Reagent: A Hypervalent Iodine Based Electrophilic Trifluoromethylation Reagent
Recyclable hypervalent-iodine-mediated solid-phase peptide synthesis and cyclic peptide synthesis
Hypervalent Iodine‐Mediated Late‐Stage Peptide and Protein Functionalization
Hypervalent Iodine‐Mediated Late‐Stage Peptide and Protein Functionalization
Hypervalent Iodine Amino Acid Building Blocks for Bioorthogonal Peptide Macrocyclization
Hypervalent Iodine Amino Acid Building Blocks for Bioorthogonal Peptide Macrocyclization
A Fluorinating Hypervalent Iodine(III) Reagent: 4-Iodotoluene Difluoride
Phosphate-Reagent-Mediated Peptide Coupling Reactions
Rapid transformation of sulfinate salts into sulfonates promoted by a hypervalent iodine(III) reagent
Solvent-dependent chemoselective synthesis of different isoquinolinones mediated by the hypervalent iodine(III) reagent PISA
Hypervalent Iodine for α,α-Dihalogenation
Peptide‐Hypervalent Iodine Reagent Chimeras: Enabling Peptide Functionalization and Macrocyclization **
Togni Reagent: A Hypervalent Iodine Based Electrophilic Trifluoromethylation Reagent
Recyclable hypervalent-iodine-mediated solid-phase peptide synthesis and cyclic peptide synthesis
Hypervalent Iodine‐Mediated Late‐Stage Peptide and Protein Functionalization
Hypervalent Iodine‐Mediated Late‐Stage Peptide and Protein Functionalization
Hypervalent Iodine Amino Acid Building Blocks for Bioorthogonal Peptide Macrocyclization
Hypervalent Iodine Amino Acid Building Blocks for Bioorthogonal Peptide Macrocyclization
A Fluorinating Hypervalent Iodine(III) Reagent: 4-Iodotoluene Difluoride
Phosphate-Reagent-Mediated Peptide Coupling Reactions
Rapid transformation of sulfinate salts into sulfonates promoted by a hypervalent iodine(III) reagent
Solvent-dependent chemoselective synthesis of different isoquinolinones mediated by the hypervalent iodine(III) reagent PISA