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Literature DB >> 29883018

BODIPY Peptide Labeling by Late-Stage C(sp³ )-H Activation.

Wei Wang¹, Mélanie M Lorion¹, Oscar Martinazzoli¹, Lutz Ackermann^1,2.

Abstract

Late-stage BODIPY diversification of structurally complex amino acids and peptides was accomplished by racemization-free palladium-catalyzed C(sp3 )-H activation. Transformative fluorescence modification proved viable by triazole-assisted C(sp3 )-H arylation in a chemo- and site-selective fashion, providing modular access to novel BODIPY peptide sensors.

Entities: Chemical Species

Keywords: BODIPY; C(sp3)−H activation; labeling; peptides; triazoles

Mesh：

Substances：

Year: 2018 PMID： 29883018 DOI： 10.1002/anie.201804654

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

15 in total

1. SCOTfluors: Small, Conjugatable, Orthogonal, and Tunable Fluorophores for In Vivo Imaging of Cell Metabolism.

Authors: Sam Benson; Antonio Fernandez; Nicole D Barth; Fabio de Moliner; Mathew H Horrocks; C Simon Herrington; Jose Luis Abad; Antonio Delgado; Lisa Kelly; Ziyuan Chang; Yi Feng; Miyako Nishiura; Yuichiro Hori; Kazuya Kikuchi; Marc Vendrell
Journal: Angew Chem Int Ed Engl Date: 2019-04-12 Impact factor: 15.336

Review 2. Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp³)-H Bonds.

Authors: Bin Liu; Andrew M Romine; Camille Z Rubel; Keary M Engle; Bing-Feng Shi
Journal: Chem Rev Date: 2021-10-29 Impact factor: 60.622

3. Organometallic Ala^M Reagents for Umpolung Peptide Diversification.

Authors: Feng Zhu; Wyatt C Powell; Ruiheng Jing; Maciej A Walczak
Journal: Chem Catal Date: 2021-06-28

4. Bioorthogonal Turn-On BODIPY-Peptide Photosensitizers for Tailored Photodynamic Therapy.

Authors: Greta Linden; Olalla Vázquez
Journal: Chemistry Date: 2020-07-23 Impact factor: 5.236

5. Macrocyclization of peptidoarylacetamides with self-assembly properties through late-stage palladium-catalyzed C(sp²)▬H olefination.

Authors: Jiantao Tan; Jie Wu; Shu Liu; Hequan Yao; Huan Wang
Journal: Sci Adv Date: 2019-03-08 Impact factor: 14.136

6. Late-stage C(sp²)-H and C(sp³)-H glycosylation of C-aryl/alkyl glycopeptides: mechanistic insights and fluorescence labeling.

Authors: Jun Wu; Nikolaos Kaplaneris; Shaofei Ni; Felix Kaltenhäuser; Lutz Ackermann
Journal: Chem Sci Date: 2020-03-24 Impact factor: 9.825

10. Synthesis of amino acids and peptides with bulky side chains via ligand-enabled carboxylate-directed γ-C(sp³)-H arylation.

Authors: Lei Liu; Yan-Hua Liu; Bing-Feng Shi
Journal: Chem Sci Date: 2019-11-11 Impact factor: 9.825

BODIPY Peptide Labeling by Late-Stage C(sp³ )-H Activation.

1. SCOTfluors: Small, Conjugatable, Orthogonal, and Tunable Fluorophores for In Vivo Imaging of Cell Metabolism.

Review 2. Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp³)-H Bonds.

3. Organometallic Ala^M Reagents for Umpolung Peptide Diversification.

4. Bioorthogonal Turn-On BODIPY-Peptide Photosensitizers for Tailored Photodynamic Therapy.

5. Macrocyclization of peptidoarylacetamides with self-assembly properties through late-stage palladium-catalyzed C(sp²)▬H olefination.

6. Late-stage C(sp²)-H and C(sp³)-H glycosylation of C-aryl/alkyl glycopeptides: mechanistic insights and fluorescence labeling.

7. Peptide late-stage C(sp³)-H arylation by native asparagine assistance without exogenous directing groups.

8. Site-selective aqueous C-H acylation of tyrosine-containing oligopeptides with aldehydes.

9. Solid-phase fluorescent BODIPY-peptide synthesis via in situ dipyrrin construction.

10. Synthesis of amino acids and peptides with bulky side chains via ligand-enabled carboxylate-directed γ-C(sp³)-H arylation.

Review 2. Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp3)-H Bonds.

Review 2. Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp³)-H Bonds.