Chemoselective ligation

Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives

Reexamination Certificate

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C514S023000, C514S062000, C536S018700, C536S055000, C536S055200, C536S053000

Reexamination Certificate

active

07667012

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: 4321366 (1982-03-01), Bobek 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: 2007/0037964 (2007-02-01), Saxon et al.
patent: WO 89/08657 (1989-09-01), None
patent: WO 01/87920 (2001-11-01), None
Paul et al., “Synthesis and Biological Activity of Some 1-N-Substituted 2-Acetamido-2-Deoxy-beta-D-Glycopyranosylamine Derivatives and Related Analogs” Carbohydrate Research (1980) vol. 80, pp. 99-115.
Kosa et al., “Modification of Cell Surfaces by Enzymatic Introduction of Special Sialic Acid Analogs” Biochemical and Biophysical Research Communications (1993) vol. 190 No. 3 pp. 914-920.
Brownlee et al. (1986) “Aminoguanidine Prevents Diabetes-Induced Arterial Wall Protein Cross-Linking.”Science, vol. 232:1629-1632.
Canne et al. (1996) “Extending the Applicability of Native Chemical Ligation.”J. Am. Chem. Soc., vol. 118:5891-5896.
Dawson et al. (1994) “Synthesis of Proteins by Native Chemical Ligation.”Science, vol. 266:776-779.
Gololobov et al. (1992) “Recent Advances in the Staudinger Reaction.” Tetrahedron, vol. 48(8):1353-1406.
Gololobov et al. (1980) “Sixty Years of Staudinger Reaction.”Tetrahedron, vol. 37:437-472.
Griffin et al. (1998) “Specific Covalent Labeling of Recombinant Protein Molecules Inside Live Cells.”Science, vol. 281:269-272.
Gumbiner (1996) “Cell Adhesion: The Molecular Basis of Tissue Architecture and Morphogenesis.”Cell, vol. 84:345-357.
Hassner et al. (1986) “Regiochemistry of Halogen Azide Addition to Allenes.”J. Org. Chem., vol. 51:2767-2770.
Herd et al. (1996) “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. 552:69-76.
Jacobs et al. (1999) “A Genetic Selection for Isolating cDNA Clones that Encode Signal Peptides.”Methods in Enzymology, vol. 303:468-479.
Kayser et al. (1992) “Biosynthesis of a Nonphysiological Sialic Acid in Different Rat Organs, Using N-Propanoyl-D-hexosamines as Precursors.”The Journal of Biological Chemistry, vol. 267(24):16934-16938.
Keppler et al. (1995) “Biosynthetic Modulation of Sialic Acid-dependent Virus-Receptor Interactions of Two Primate Polyoma Viruses.”The Journal of Biological Chemistry, vol. 270(3):1308-1314.
Khoukhi et al. (1986) “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, vol. 27(9):1031-1034.
Kiick et al. (2000) “Protein Engineering by In Vivo Incorporation of Non-Natural Amino Acids: Control of Incorporation of Methionine Analogues by Methionyl-tRNA Synthetase.”Tetrahedron, vol. 56:9487-9493.
Kosa et al. (1993) “Modification of Cell Surfaces by Enzymatic Introduction of Special Sialic Acid Analogues.”Biochemical and Biophysical Research Communications, vol. 190(3):914-921.
Lee et al. (1999) “Engineering Novel Cell Surface Receptors for Virus-mediated Gene Transfer.”The Journal of Biological Chemistry, vol. 274(31):21878-21884.
Leffler et al. (1967) “The Staudinger Reaction between Triarylphosphines and Azides. A Study of the Mechanism.”J. Am. Chem. Soc., vol. 89:5235-5246.
Lemieux et al. (1998) “Chemoselective ligation reactions with proteins, oligosaccharides and cells.”Trends Biotechnol., vol. 16:506-513.
Lemieux et al. (1999) “Exploiting Differences in Sialoside Expression for Selective Targeting of MRI Contrast Reagents.”J. Am. Chem. Soc., vol. 121:4278-4279.
Mahal et al. (1997) “Engineering Chemical Reactivity on Cell Surfaces through Oligosaccharide biosynthesis.”Science, vol. 276:1125-1128.
Marcaurelle et al. (1998) “Direct Incorporation of Unprotected Ketone Groups into Peptides During Solid-Phase Synthesis: Application to the One-Step Modification of Peptides with Two Different Biophysical Probes for FRET.”Tetrahedron Letters, vol. 39:7279-7282.
Marcaurelle et al. (1998) “Synthesis of an Oxime-Linked Neoglycopeptide with Glycosylation-dependent Activity similar to its Native Counterpart.”Tetrahedron Letters, vol. 39:8417-8420.
Mastryukova et al. (1989) “Amide-Imide Rearrangement in β-Chloroethyl Esters of Phosphorus Acid N-Phenylimides.”Zh. Obshch. Khim., vol. 58(9):1967-1973.
Rodriguez et al. (1998) “Aminooxy-, Hydrazide-, and Thiosemicarbazide-Functionalized Saccharides: Versatile Reagents for Glycoconjugate Synthesis.”J. Org. Chem., vol. 63:7134-7135.
Sarkar et al. (1995) “Disaccharide uptake and priming in animal cells: Inhibition of sialyl Lewis X by acetylated Galβ1→4GlcNAcβ-O-naphthalenemethanol.”Proc. Natl. Acad. Sci. USA, vol. 92:3323-3327.
Slany et al. (1996) “Specific Functionalization on the Surface of Dendrimers.”Tetrahedron Letters, vol. 37(50):9053-9056.
Souers et al. (1999) “Preparation of Enantioenriched α-Bromo Acids Incorporating Diverse Functionality.”Synthesis-Stuttgart, vol. 4:583-585.
Staudinger et al. (1919) “Über neue organische Phosphorverbindunge III. Phosphinmethylenderivate und Phosphinime.”Helv. Chim. Acta., vol. 2:635-646.
Wilt et al. (1985) “A New synthesis of Peptides from Azides and Unactivated Carboxylic Acids.”J. Org. Chem., vol. 50:2601-2603.
Winans et al. (1998) “Inner space exploration: the chemical biologist's guide to the cell.”Chemistry&Biology, vol. 5:R313-R315.
Yarema et al. (1998) “Metabolic Delivery of Ketone Groups to Sialic Acid Residues.”The Journal of Biological Chemistry, vol. 273(47):31168-31179.
Ravinder, et al. 1992, Synth, Comm., 22, pp. 1453-1459.
Chatt et al. (1973) Rhodium(I), Rhodium(III), Palladium(II), and Platinum(II) complexes containing Ligands of the TypePRnQ3-n(n=0,1,or2; R= Me, Et, Bu, or Ph; Q=CH2OCOMe or Ch2OH). Journal of Chemical Society No. 19 pp. 2021-2028.
Markl et al (1980) 1,5-Diaza-3-phopha-cyclohepatne-N,N′-Bis-′[phosphinomethyl]-Ethylendiamine MIT Optisch Aktiven Seitenketten, Tetrahedron Letters vol. 21 pp. 3467-3470.
Saxon et al. (Mar. 17, 2000) Cell Surface Engineering by a Modified Staudinger Reaction. Science vol. 287 No. 5460 pp. 2007-2010.
Saxon et al.(1999) Development of a New Chemoselective Ligation Reaction, Abstracts of Papers American Chemical Society vol. 218 No. 1-2 PP. Carb 23.
Hingst, M., et al. Nucleophilic phosphanylation of the fluoromatic compounds with carboxyl, carboxymethyl, and aminomethyl functionalities - and efficient synthetic route to amphiphilic arylphosphanes. European Journal Inorganic Chemistry. 1998, vol. 1, pp. 73-82.

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