Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Reexamination Certificate
2007-10-18
2010-11-23
Sullivan, Daniel M (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
C548S304100, C562S553000, C564S012000, C564S015000, C568S013000
Reexamination Certificate
active
07838665
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).
REFERENCES:
patent: 4292437 (1981-09-01), Squire et al.
patent: 5874628 (1999-02-01), Laneman et al.
patent: 5925785 (1999-07-01), Stelzer et al.
patent: 6570040 (2003-05-01), Saxon et al.
patent: 7122703 (2006-10-01), Saxon et al.
patent: 2005/0148032 (2005-07-01), Saxon et al.
patent: 2006/0276658 (2006-12-01), Saxon et al.
patent: 2007/0037964 (2007-02-01), Saxon et al.
patent: WO 89/08657 (1989-09-01), None
patent: WO 01/87920 (2001-11-01), None
Hingst et al., {Water-soluble phosphines. Part 9. Nucleophilic phosphinylation of fluoro aromatic compounds with carboxyl, carboxymethyl, and aminomethyl functionalities. An efficient synthetic route to amphiphilic arylphosphines, European Journal of Inorganic Chemistry (1998), (1), 73-82}.
Ager et al. Convenient and direct preparation of tertiary phosphines via nickel-catalyzed cross-coupling. Chemical Communications (Cambridge). 1997, vol. 24, pp. 2359-2360.
Breit. Probing new classes of p-acceptor ligands for rhodium catalyzed hydroformylation of styrene. Journal of Molecular Catalysis A: Chemical. 1999, vol. 143 (1-3), pp. 143-154.
Breit. Substrate-directed diastereoselective hydroaminomethylation of methallyic alcohols. Tetrahedron Letters. 1998, vol. 39, No. 29, pp. 5163-5166.
Breit. Substrate-directed diastereoselective hydroformylations. Part 1. Substrate-directed diastereoselective hydroformylation of methallylic alcohols. Development of an efficient catalyst-directing group for rhodium-catalyzed hydroformylation. Liebigs Annalen/Recueil. 1997, vol. 9, pp. 1841-1851.
Brownlee et al. Aminoguanidine Prevents Diabetes-Induced Arterial Wall Protein Cross-Linking. Science. 1986, vol. 232, pp. 1629-1632.
Canne et al. Extending the Applicability of Native Chemical Ligation. J Am Chem Soc. 1996, vol. 118, pp. 5891-5896.
Chatt et al. Rhodium(I), Rhodium(III), Palladium(II), and Platinum(II) complexes containing Ligands of the TypePR.sup.n. Q.sub.3-n (n=0,1,or2; R= Me, Et, Bu, or Ph; Q=CH.sub.2 OCOMe or Ch.sub.2 OH). Journal of Chemical Society. 1973, No. 19, pp. 2021-2028..
Dawson et al. Synthesis of Proteins by Native Chemical Ligation. Science. 1994, vol. 266, pp. 776-779.
Gololobov et al. Recent Advances in the Staudinger Reaction. Tetrahedron. 1992, vol. 48, No. 8, pp. 1353-1406.
Gololobov et al. Sixty Years of Staudinger Reaction. Tetrahedron. 1980, vol. 37, pp. 437-472.
Griffin et al. Specific Covalent Labeling of Recombinant Protein Molecules Inside Live Cells. Science. 1998, vol. 281, pp. 269-272.
Gumbiner. Cell Adhesion: The Molecular Basis of Tissue Architecture and Morphogenesis. Cell. 1996, vol. 84, pp. 345-357.
Hassner et al. Regiochemistry of Halogen Azide Addition to Allenes. J Org Chem. 1986, vol. 51, pp. 2767-2770.
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. 1996, vol. 552, pp. 69-76.
Jacobs et al. A Genetic Selection for Isolating cDNA Clones that Encode Signal Peptides. Methods in Enzymology. 1999, vol. 303, pp. 468-479.
Kayser et al. Biosynthesis of a Nonphysiological Sialic Acid in Different Rat Organs, Using N-Propanoyl-D-hexosamines as Precursors. The Journal of Biological Chemistry. 1992, vol. 267, No. 24, pp. 16934-16938.
Keppler et al. Biosynthetic Modulation of Sialic Acid-dependent Virus-Receptor Interactions of Two Primate Polyoma Viruses. The Journal of Biological Chemistry. 1995, vol. 270, No. 3, pp. 1308-1314.
Khoukhi et al. The Use of ω-Iodoazides as Primary Protected Electrophilic Reagents. Alkylation of some Carbanions Derived from Active Methylene Compounds and N,N-Dimethylhydrazones. Tetrahedron Letters. 1986, vol. 27, No. 9, pp. 1031-1034.
Kiick et al. Protein Engineering by In Vivo Incorporation of Non-Natural Amino Acids Control of Incorporation of Methionine Analogues by Methionyl-tRNA Synthetase. Tetrahedron. 2000, vol. 56, pp. 9487-9493.
Kosa et al. Modification of Cell Surfaces by Enzymatic Introduction of Special Sialic Acid Analogues. Biochemical and Biophysical Research Communications. 1993, vol. 190, No. 3, pp. 914-921.
Lee et al. Engineering Novel Cell Surface Receptors for Virus-mediated Gene Transfer. The Journal of Biological Chemistry. 1999, vol. 274, No. 31, pp. 21878-21884.
Leffler et al. The Staudinger Reaction between Triarylphosphines and Azides. A Study of the Mechanism. J Am Chem Soc. 1967, vol. 89, pp. 5235-5246.
Lemieux et al. Chemoselective ligation reactions with proteins, oligosaccharides and cells. Trends Biotechnol. 1998, vol. 16, pp. 506.
Lemieux et al. Exploiting Differences in Sialoside Expression for Selective Targeting of MRI Contrast Reagents. J Am Chem Soc. 1999, vol. 121, pp. 4278-4279.
Mahal et al. Engineering Chemical Reactivity on Cell Surfaces through Oligosaccharide biosynthesis. Science. 1997, vol. 276, pp. 1125-1128.
Marcaurelle et al. Direct Incorporation of Unprotected Ketone Groups into Peptides During Solid-Phase Syntheiss: Application to the One-Step Modification of Peptides with Two Different Biophysical Probes for FRET. Tetrahedron Letters. 1998, vol. 39, pp. 7279-7282.
Marcaurelle et al. Synthesis of an Oxime-Linked Neoglycopeptide with Glycosylation-dependent Activity similar to its Native Counterpart. Tetrahedron Letters. 1998, vol. 39, pp. 8417-8420.
Markl et al. 1,5-Diaza-3-phopha-cyclohepatne-N,N‘-Bis-’[phosphinomethyl]-Ethylendiamine MIT Optisch Aktiven Seitenketten. Tetrahedron Letters. 1980, vol. 21, pp. 3467-3470.
Mastryukova et al. Amide-Imide Rearrangement in .beta.-Chloroethyl Esters of Phosphorus Acid N-Phenylimides. Zh Obshch Khim. 1989, vol. 58, No. 9, pp. 1967-1973.
Mecking et al. Cationic Palladium h3-Allyl Complexes with Hemilabile P, O-Ligands: Synthesis and Reactivity. Insertion of Ethylene into the Pd-Allyl Function. Organometallics. 1996, vol. 15, No. 11, pp. 2650-2656.
Panchenko et al. The IRS-DR study of interaction of the supported catalyst based on the organic nickel chelate with carbon monoxide and ethylene. Journal of Molecular Catalyst A: Chemical. 1998, vol. 135, No. 2, pp. 115-120.
Ravindar et al. A Novel Convenient Synthesis of Aryl Phosphines Containing Reactive Functional Groups. Synth Comm. 1992, vol. 22, pp. 1453-1459.
Rodriguez et al. Aminooxy-, Hydrazide-, and Thiosemicarbazide-Functionalized Saccharides: Versatile Reagents for Glycoconjugate Synthesis. J Org Chem. 1998, vol. 63, pp. 7134-7135.
Sarkar et al. Disaccharide uptake and priming in animal cells: Inhibition of sialyl Lewis X by acetylated Gal.beta.1.fwdarw.4GIcNAc.beta.-O-naphthalenemethanol. Proc Natl Acad Sci USA. 1995, vol. 92, pp. 3323-3327.
Saxon et al. A “Traceless” Staudinger Ligation for the Chemoselective Synthesis of Amide Bonds, Organic Letters. 2000, vol. 2, No. 14, pp. 2141-2143.
Saxon et al. Cell Surface Engineering by a Modified Staudinger Reaction. Science. Mar. 17, 2000, vol. 287, No. 5460, pp. 2007.
Saxon et al. Development of a New Chemoselective Ligation Reaction. Abstracts of Papers American Chemical Society. 1999, vol. 218, No. 1-2, pp. Carb 23.
Slany et al. Specific Functionalization on the Surface of Dendrimers. Tetrahedron Letters. 1996, vo
Bertozzi Carolyn Ruth
Saxon Eliana
Borden Paula A.
Bozicevic Field & Francis LLP
Nwaonicha Chukwuma O
Sullivan Daniel M
The Regents of the University of California
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