Bioorthogonal organic chemistry in living cells: novel strategies for labeling biomolecules
- PMID: 15602593
- DOI: 10.1039/b412558d
Bioorthogonal organic chemistry in living cells: novel strategies for labeling biomolecules
Abstract
The chemical labeling of biomolecules continues to be an important tool for the study of their function and cellular fate. Attention is increasingly focused on labeling of biomolecules in living cells, since cell lysis introduces many artefacts. In addition, with the advances in biocompatible synthetic organic chemistry, a whole new field of opportunity has opened up, affording high diversity in the nature of the label as well as a choice of ligation reactions. In recent years, several different two-step labeling strategies have emerged. These rely on the introduction of a bioorthogonal attachment site into a biomolecule, then ligation of a reporter molecule to this site using bioorthogonal organic chemistry. This Perspective focuses on these techniques, their implications and future directions.
Similar articles
-
Click chemistry and bioorthogonal reactions: unprecedented selectivity in the labeling of biological molecules.Biochemistry. 2009 Jul 21;48(28):6571-84. doi: 10.1021/bi9007726. Biochemistry. 2009. PMID: 19485420 Review.
-
Chemistry in living systems.Nat Chem Biol. 2005 Jun;1(1):13-21. doi: 10.1038/nchembio0605-13. Nat Chem Biol. 2005. PMID: 16407987 Review.
-
A designed protein for the specific and covalent heteroconjugation of biomolecules.Bioconjug Chem. 2008 Sep;19(9):1753-6. doi: 10.1021/bc800268j. Epub 2008 Aug 28. Bioconjug Chem. 2008. PMID: 18754573
-
Selective chemical labeling of proteins in living cells.Curr Opin Chem Biol. 2005 Feb;9(1):56-61. doi: 10.1016/j.cbpa.2004.12.007. Curr Opin Chem Biol. 2005. PMID: 15701454 Review.
-
Introducing bioorthogonal functionalities into proteins in living cells.Acc Chem Res. 2011 Sep 20;44(9):742-51. doi: 10.1021/ar200067r. Epub 2011 Jun 2. Acc Chem Res. 2011. PMID: 21634380
Cited by
-
Evaluation of sulfatase-directed quinone methide traps for proteomics.Bioorg Med Chem. 2012 Jan 15;20(2):622-7. doi: 10.1016/j.bmc.2011.04.044. Epub 2011 Apr 24. Bioorg Med Chem. 2012. PMID: 21570853 Free PMC article.
-
Dechalcogenative allylic selenosulfide and disulfide rearrangements: complementary methods for the formation of allylic sulfides in the absence of electrophiles. Scope, limitations, and application to the functionalization of unprotected peptides in aqueous media.J Am Chem Soc. 2007 Aug 22;129(33):10282-94. doi: 10.1021/ja072969u. Epub 2007 Jul 27. J Am Chem Soc. 2007. PMID: 17655306 Free PMC article.
-
Metabolic glycan imaging by isonitrile-tetrazine click chemistry.Chembiochem. 2013 Jun 17;14(9):1063-7. doi: 10.1002/cbic.201300130. Epub 2013 May 13. Chembiochem. 2013. PMID: 23670994 Free PMC article.
-
Allylic selenosulfide rearrangement: a method for chemical ligation to cysteine and other thiols.J Am Chem Soc. 2006 Mar 1;128(8):2544-5. doi: 10.1021/ja057521c. J Am Chem Soc. 2006. PMID: 16492032 Free PMC article.
-
Synthesis and spectroscopic characterization of fluorescent boron dipyrromethene-derived hydrazones.J Fluoresc. 2011 Jan;21(1):347-54. doi: 10.1007/s10895-010-0723-0. Epub 2010 Oct 1. J Fluoresc. 2011. PMID: 20886269 Free PMC article.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Other Literature Sources