Title:
CHEMOSELECTIVE LIGATION BY USE OF A PHOSPHINE
Document Type and Number:
WIPO Patent Application WO2001068565
Kind Code:
A3
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:
BERTOZZI CAROLYN
SAXON ELIANA
SAXON ELIANA
Application Number:
PCT/US2001/008546
Publication Date:
May 23, 2002
Filing Date:
March 16, 2001
Export Citation:
Assignee:
UNIV CALIFORNIA (US)
International Classes:
C07F9/50; C07F9/6506; C07F9/655; C07F9/6561; C07K1/02; C07K1/04; C07K1/107; C12N5/02; (IPC1-7): C07K1/107; C07K9/00; A61K47/48; C07F9/655; C07F9/6561; C07F9/50; C07F9/6506; C07K1/04
Domestic Patent References:
| WO1989008657A2 | 1989-09-21 |
Other References:
SAXON, ELIANA (1) ET AL: "Development of a new chemoselective ligation reaction.", ABSTRACTS OF PAPERS AMERICAN CHEMICAL SOCIETY, (1999) VOL. 218, NO. 1-2, PP. CARB 23. MEETING INFO.: 218TH NATIONAL MEETING OF THE AMERICAN CHEMICAL SOCIETY, PARTS 1 AND 2 NEW ORLEANS, LOUISIANA, USA AUGUST 22-26, 1999 AMERICAN CHEMICAL SOCIETY., XP001059669
O HERD ET AL: "Water-soluble phosphines VIII. Palladium-catalyzed P-C cross coupling reactions between primary or secondary phosphines and functional aryliodides - a novel synthetic route to water-soluble phosphines", JOURNAL OF ORGANOMETALLIC CHEMISTRY., vol. 522, 1996, ELSEVIER-SEQUOIA S.A. LAUSANNE., CH, pages 69 - 76, XP002188898, ISSN: 0022-328X
J CHATT ET AL.: "Rhodium(I), rhodium(II), palladium(II) and platinum(II) complexes containing ligands of the type PRnQ3-n (n=0, 1 or 2; R=Mem Et, But or Ph; Q=CH2OCOMe or CH2OH)", JOURNAL OF THE CHEMICAL SOCIETY, DALTON TRANSACTIONS., no. 19, 1973, CHEMICAL SOCIETY. LETCHWORTH., GB, pages 2021 - 2028, XP002188899, ISSN: 1472-7773
G MÄRKL & G YU JIN: "1,5-Diaza-3-phospha-cycloheptane-N,N'-Bis-[phosphinomethyl]-ethylendiamine mit optisch aktiven Seitenketten", TETRAHEDRON LETTERS., vol. 21, 1980, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM., NL, pages 3467 - 3470, XP002188900, ISSN: 0040-4039
SAXON, ELIANA ET AL: "Cell surface engineering by a modified Staudinger reaction.", SCIENCE (WASHINGTON D C), (MARCH 17, 2000) VOL. 287, NO. 5460, PP. 2007-2010. PRINT., XP002188901
O HERD ET AL: "Water-soluble phosphines VIII. Palladium-catalyzed P-C cross coupling reactions between primary or secondary phosphines and functional aryliodides - a novel synthetic route to water-soluble phosphines", JOURNAL OF ORGANOMETALLIC CHEMISTRY., vol. 522, 1996, ELSEVIER-SEQUOIA S.A. LAUSANNE., CH, pages 69 - 76, XP002188898, ISSN: 0022-328X
J CHATT ET AL.: "Rhodium(I), rhodium(II), palladium(II) and platinum(II) complexes containing ligands of the type PRnQ3-n (n=0, 1 or 2; R=Mem Et, But or Ph; Q=CH2OCOMe or CH2OH)", JOURNAL OF THE CHEMICAL SOCIETY, DALTON TRANSACTIONS., no. 19, 1973, CHEMICAL SOCIETY. LETCHWORTH., GB, pages 2021 - 2028, XP002188899, ISSN: 1472-7773
G MÄRKL & G YU JIN: "1,5-Diaza-3-phospha-cycloheptane-N,N'-Bis-[phosphinomethyl]-ethylendiamine mit optisch aktiven Seitenketten", TETRAHEDRON LETTERS., vol. 21, 1980, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM., NL, pages 3467 - 3470, XP002188900, ISSN: 0040-4039
SAXON, ELIANA ET AL: "Cell surface engineering by a modified Staudinger reaction.", SCIENCE (WASHINGTON D C), (MARCH 17, 2000) VOL. 287, NO. 5460, PP. 2007-2010. PRINT., XP002188901
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