| Tyrosine bioconjugation through aqueous ene-type reactions: a click-like reaction for tyrosine. | |
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MedLine Citation:
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PMID: 20067259 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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A new and versatile class of cyclic diazodicarboxamides that reacts efficiently and selectively with phenols and the phenolic side chain of tyrosine through an ene-like reaction is reported. This mild aqueous tyrosine ligation reaction works over a broad pH range and expands the repertoire of aqueous chemistries available for small molecule, peptide, and protein modification. The tyrosine ligation reactions are shown to be compatible with the labeling of native enzymes and antibodies in a buffered aqueous solution. This reaction provides a novel synthetic approach to bispecific antibodies. We believe this reaction will find broad utility in peptide and protein chemistry and in the chemistry of phenol-containing compounds. |
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Authors:
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Hitoshi Ban; Julia Gavrilyuk; Carlos F Barbas |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Journal of the American Chemical Society Volume: 132 ISSN: 1520-5126 ISO Abbreviation: J. Am. Chem. Soc. Publication Date: 2010 Feb |
Date Detail:
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Created Date: 2010-02-03 Completed Date: 2010-03-12 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 7503056 Medline TA: J Am Chem Soc Country: United States |
Other Details:
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Languages: eng Pagination: 1523-5 Citation Subset: IM |
Affiliation:
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The Skaggs Institute for Chemical Biology, 10550 North Torrey Pines Road, La Jolla, California 92037, USA. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Animals Cattle Chymotrypsinogen / chemistry Molecular Structure Myoglobin / chemistry Proteins / chemistry* Serum Albumin, Bovine / metabolism Tyrosine / chemistry* Water / chemistry |
| Chemical | |
Reg. No./Substance:
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0/Myoglobin; 0/Proteins; 0/Serum Albumin, Bovine; 55520-40-6/Tyrosine; 7732-18-5/Water; 9035-75-0/Chymotrypsinogen |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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