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A strain-promoted [3 + 2] azide-alkyne cycloaddition for covalent modification of biomolecules in living systems.

A strain-promoted [3 + 2] azide-alkyne cycloaddition for covalent modification of biomolecules in living systems. Research Abstract Details 

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  • A strain-promoted [3 + 2] azide-alkyne cycloaddition for covalent modification of biomolecules in living systems. Abstract Text:

    nicholas j agardNicholas J Agard,jennifer a prescherJennifer A Prescher,carolyn r bertozziCarolyn R Bertozzi,

    Selective chemical reactions that are orthogonal to the diverse functionality of biological systems have become important tools in the field of chemical biology. Two notable examples are the Staudinger ligation of azides and phosphines and the Cu(I)-catalyzed [3 + 2] cycloaddition of azides and alkynes ("click chemistry"). The Staudinger ligation has sufficient biocompatibility for performance in living animals but suffers from phosphine oxidation and synthetic challenges. Click chemistry obviates the requirement of phosphines, but the Cu(I) catalyst is toxic to cells, thereby precluding in vivo applications. Here we present a strain-promoted [3 + 2] cycloaddition between cyclooctynes and azides that proceeds under physiological conditions without the need for a catalyst. The utility of the reaction was demonstrated by selective modification of biomolecules in vitro and on living cells, with no apparent toxicity.

    A strain-promoted [3 + 2] azide-alkyne cycloaddition for covalent modification of biomolecules in living systems. Publishing Authors By Initials

    nj agardNJ Agard,ja prescherJA Prescher,cr bertozziCR Bertozzi,

    For similar cells: cells, cultured: cell line: cell line, tumor: jurkat cells research abstracts see: cells: cells, cultured: cell line: cell line, tumor: jurkat cells research

    PUBMED ID PMID:

    MEDLINE DATE:

    A strain-promoted [3 + 2] azide-alkyne cycloaddition for covalent modification of biomolecules in living systems. Journal Published:

    PUBLICATION TYPE: Research Support, U.S. Gov't,

    Journal: Journal of the American Chemical Society

    VOLUME: 126

    Page Numbers: 15046-7

    Journal Abbreviation: J. Am. Chem. Soc.

    ISSN: 0002-7863

    DAY: 24

    MONTH: Nov

    YEAR: 2004

    A strain-promoted [3 + 2] azide-alkyne cycloaddition for covalent modification of biomolecules in living systems. Information

    Number of References:

    LANGUAGE: eng

    NlmUniqueID: 7503056

    A strain-promoted [3 + 2] azide-alkyne cycloaddition for covalent modification of biomolecules in living systems. Keywords Mesh Terms:

    KEYWORDS: Jurkat Cells

    MESH TERMS: metabolism

    Chemical & Substance for Abstract: A strain-promoted [3 + 2] azide-alkyne cycloaddition for covalent modification of biomolecules in living systems. Information

    Substance Name: Biotin

    Registry Number: 58-85-5

    Grant and Affiliation Information for A strain-promoted [3 + 2] azide-alkyne cycloaddition for covalent modification of biomolecules in living systems.

    AFFILIATION: Department of Chemistry, Howard Hughes Medical Institute, University of California, and Materials Sciences Division, Lawrence Berkeley National Laboratory, Berkeley, California 94720, USA.

    Country: United States

    United States Research PublicationUnited States Research Publication

    AGENCY: United States NIGMS

    GRANT: GM58867

    ACRONYM: GM

    MEDLINETA: J Am Chem Soc

    REFSOURCE: J Am Chem Soc. 2005 Aug 10;127(31):11196

    DATABASENAME:

    ACCESSION NUMBER:

    Number Hits: 0

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