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Direct meso ‐Alkynylation of Metalloporphyrins Through Gold Catalysis for Hemoprotein Engineering

A method was developed for the direct functionalization of metalloporphyrins at the methine protons (meso positions) to yield asymmetric alkynylated derivatives by using gold catalysis and hypervalent iodine reagents. This single‐step procedure was applied to ‐type heme and the product was incorpora... Full description

Journal Title: Angewandte Chemie International Edition 03 March 2014, Vol.53(10), pp.2611-2614
Main Author: Nierth, Alexander
Other Authors: Marletta, Michael A.
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 1433-7851 ; E-ISSN: 1521-3773 ; DOI: 10.1002/anie.201310145
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recordid: wj10.1002/anie.201310145
title: Direct meso ‐Alkynylation of Metalloporphyrins Through Gold Catalysis for Hemoprotein Engineering
format: Article
creator:
  • Nierth, Alexander
  • Marletta, Michael A.
subjects:
  • Chemical Biology
  • Click Chemistry
  • Heme Proteins
  • H‐Nox Proteins
  • Transition Metal Catalysis
ispartof: Angewandte Chemie International Edition, 03 March 2014, Vol.53(10), pp.2611-2614
description: A method was developed for the direct functionalization of metalloporphyrins at the methine protons (meso positions) to yield asymmetric alkynylated derivatives by using gold catalysis and hypervalent iodine reagents. This single‐step procedure was applied to ‐type heme and the product was incorporated into a gas‐sensor heme protein. The terminal alkyne allows fluorophore labeling through copper(I)‐catalyzed azide–alkyne cycloaddition (CuAAC). Hemoproteins with this type of engineered cofactor have several potential applications in labeling and imaging technologies. Additionally, the alkyne provides a handle for modulating porphyrin electron density, which affects cofactor redox potential and ligand affinity. This method will be helpful for investigating the chemistry of natural heme proteins and for designing artificial variants with altered properties and reactivities. : Metalloporphyrins can be directly functionalized at the methine protons ( positions) to yield asymmetric alkynylated derivatives by using gold catalysis and hypervalent iodine reagents. This single‐step procedure was applied to ‐type heme and the product was incorporated into a gas‐sensor heme protein. The terminal alkyne allows fluorophore labeling through copper(I)‐catalyzed azide–alkyne cycloaddition.
language: eng
source:
identifier: ISSN: 1433-7851 ; E-ISSN: 1521-3773 ; DOI: 10.1002/anie.201310145
fulltext: fulltext
issn:
  • 1433-7851
  • 14337851
  • 1521-3773
  • 15213773
url: Link


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titleDirect meso ‐Alkynylation of Metalloporphyrins Through Gold Catalysis for Hemoprotein Engineering
creatorNierth, Alexander ; Marletta, Michael A.
ispartofAngewandte Chemie International Edition, 03 March 2014, Vol.53(10), pp.2611-2614
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subjectChemical Biology ; Click Chemistry ; Heme Proteins ; H‐Nox Proteins ; Transition Metal Catalysis
descriptionA method was developed for the direct functionalization of metalloporphyrins at the methine protons (meso positions) to yield asymmetric alkynylated derivatives by using gold catalysis and hypervalent iodine reagents. This single‐step procedure was applied to ‐type heme and the product was incorporated into a gas‐sensor heme protein. The terminal alkyne allows fluorophore labeling through copper(I)‐catalyzed azide–alkyne cycloaddition (CuAAC). Hemoproteins with this type of engineered cofactor have several potential applications in labeling and imaging technologies. Additionally, the alkyne provides a handle for modulating porphyrin electron density, which affects cofactor redox potential and ligand affinity. This method will be helpful for investigating the chemistry of natural heme proteins and for designing artificial variants with altered properties and reactivities. : Metalloporphyrins can be directly functionalized at the methine protons ( positions) to yield asymmetric alkynylated derivatives by using gold catalysis and hypervalent iodine reagents. This single‐step procedure was applied to ‐type heme and the product was incorporated into a gas‐sensor heme protein. The terminal alkyne allows fluorophore labeling through copper(I)‐catalyzed azide–alkyne cycloaddition.
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descriptionA method was developed for the direct functionalization of metalloporphyrins at the methine protons (meso positions) to yield asymmetric alkynylated derivatives by using gold catalysis and hypervalent iodine reagents. This single‐step procedure was applied to ‐type heme and the product was incorporated into a gas‐sensor heme protein. The terminal alkyne allows fluorophore labeling through copper(I)‐catalyzed azide–alkyne cycloaddition (CuAAC). Hemoproteins with this type of engineered cofactor have several potential applications in labeling and imaging technologies. Additionally, the alkyne provides a handle for modulating porphyrin electron density, which affects cofactor redox potential and ligand affinity. This method will be helpful for investigating the chemistry of natural heme proteins and for designing artificial variants with altered properties and reactivities. : Metalloporphyrins can be directly functionalized at the methine protons ( positions) to yield asymmetric alkynylated derivatives by using gold catalysis and hypervalent iodine reagents. This single‐step procedure was applied to ‐type heme and the product was incorporated into a gas‐sensor heme protein. The terminal alkyne allows fluorophore labeling through copper(I)‐catalyzed azide–alkyne cycloaddition.
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abstractA method was developed for the direct functionalization of metalloporphyrins at the methine protons (meso positions) to yield asymmetric alkynylated derivatives by using gold catalysis and hypervalent iodine reagents. This single‐step procedure was applied to ‐type heme and the product was incorporated into a gas‐sensor heme protein. The terminal alkyne allows fluorophore labeling through copper(I)‐catalyzed azide–alkyne cycloaddition (CuAAC). Hemoproteins with this type of engineered cofactor have several potential applications in labeling and imaging technologies. Additionally, the alkyne provides a handle for modulating porphyrin electron density, which affects cofactor redox potential and ligand affinity. This method will be helpful for investigating the chemistry of natural heme proteins and for designing artificial variants with altered properties and reactivities. : Metalloporphyrins can be directly functionalized at the methine protons ( positions) to yield asymmetric alkynylated derivatives by using gold catalysis and hypervalent iodine reagents. This single‐step procedure was applied to ‐type heme and the product was incorporated into a gas‐sensor heme protein. The terminal alkyne allows fluorophore labeling through copper(I)‐catalyzed azide–alkyne cycloaddition.
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doi10.1002/anie.201310145
pages2611-2614
date2014-03-03