Chemoselective ligation
Abstract
The present invention features a chemoselective ligation reaction that can be carried out under physiological conditions. In general, the invention involves condensation of a specifically engineered phosphine, which can provide for formation of an amide bond between the two reactive partners resulting in a final product comprising a phosphine moiety, or which can be engineered to comprise a cleavable linker so that a substituent of the phosphine is transferred to the azide, releasing an oxidized phosphine byproduct and producing a native amide bond in the final product. The selectivity of the reaction and its compatibility with aqueous environments provides for its application in vivo (e.g., on the cell surface or intracellularly) and in vitro (e.g., synthesis of peptides and other polymers, production of modified (e.g., labeled) amino acids).
- Inventors:
-
- Albany, CA
- Berkeley, CA
- Issue Date:
- Research Org.:
- Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)
- Sponsoring Org.:
- USDOE
- OSTI Identifier:
- 921799
- Patent Number(s):
- 6570040
- Application Number:
- 09/810,864
- Assignee:
- The Regents of the University of California (Oakland, CA)
- Patent Classifications (CPCs):
-
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07F - ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07H - SUGARS
- DOE Contract Number:
- AC03-76SF00098
- Resource Type:
- Patent
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Citation Formats
Saxon, Eliana, and Bertozzi, Carolyn. Chemoselective ligation. United States: N. p., 2003.
Web.
Saxon, Eliana, & Bertozzi, Carolyn. Chemoselective ligation. United States.
Saxon, Eliana, and Bertozzi, Carolyn. Tue .
"Chemoselective ligation". United States. https://www.osti.gov/servlets/purl/921799.
@article{osti_921799,
title = {Chemoselective ligation},
author = {Saxon, Eliana and Bertozzi, Carolyn},
abstractNote = {The present invention features a chemoselective ligation reaction that can be carried out under physiological conditions. In general, the invention involves condensation of a specifically engineered phosphine, which can provide for formation of an amide bond between the two reactive partners resulting in a final product comprising a phosphine moiety, or which can be engineered to comprise a cleavable linker so that a substituent of the phosphine is transferred to the azide, releasing an oxidized phosphine byproduct and producing a native amide bond in the final product. The selectivity of the reaction and its compatibility with aqueous environments provides for its application in vivo (e.g., on the cell surface or intracellularly) and in vitro (e.g., synthesis of peptides and other polymers, production of modified (e.g., labeled) amino acids).},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {Tue May 27 00:00:00 EDT 2003},
month = {Tue May 27 00:00:00 EDT 2003}
}
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