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Title: 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:
 [1];  [2]
  1. Albany, CA
  2. Berkeley, CA
Issue Date:
Research Org.:
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1034298
Patent Number(s):
8076496
Application Number:
13/043,274
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 Ruth. Chemoselective ligation. United States: N. p., 2011. Web.
Saxon, Eliana, & Bertozzi, Carolyn Ruth. Chemoselective ligation. United States.
Saxon, Eliana, and Bertozzi, Carolyn Ruth. Tue . "Chemoselective ligation". United States. https://www.osti.gov/servlets/purl/1034298.
@article{osti_1034298,
title = {Chemoselective ligation},
author = {Saxon, Eliana and Bertozzi, Carolyn Ruth},
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 = {2011},
month = {12}
}

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