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:

Saxon, Eliana ^[1]; Bertozzi, Carolyn R ^[2]

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1. Albany, CA
2. Berkeley, CA

Issue Date:

2010-02-23

Research Org.:

Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)

Sponsoring Org.:

USDOE

OSTI Identifier:

1015197

Patent Number(s):

7667012

Application Number:

11/408,605

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

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C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07F - ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM

C07F9/5022 - {Aromatic phosphines
C07F9/6506 - having the nitrogen atoms in positions 1 and 3
C07F9/65522 - {condensed with carbocyclic rings or carbocyclic ring systems}
C07F9/6561 - containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07H - SUGARS

C07H13/00 - Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
C07H15/203 - Monocyclic carbocyclic rings other than cyclohexane rings
C07H15/26 - Acyclic or carbocyclic radicals, substituted by hetero rings
C07H7/02 - Acyclic radicals

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07K - PEPTIDES

C07K1/023 - {using racemisation inhibiting agents}
C07K1/04 - on carriers {
C07K1/1075 - {by covalent attachment of amino acids or peptide residues}
C07K1/1077 - {by covalent attachment of residues other than amino acids or peptide residues, e.g. sugars, polyols, fatty acids}

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DOE Contract Number:  

AC03-76SF00098

Resource Type:

Patent

Country of Publication:

United States

Language:

English