Chemistry: natural resins or derivatives; peptides or proteins; – Peptides of 3 to 100 amino acid residues – 25 or more amino acid residues in defined sequence
Reexamination Certificate
2011-05-10
2011-05-10
Sullivan, Daniel M (Department: 1621)
Chemistry: natural resins or derivatives; peptides or proteins;
Peptides of 3 to 100 amino acid residues
25 or more amino acid residues in defined sequence
C530S350000, C568S017000
Reexamination Certificate
active
07939626
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: 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: WO 89/08657 (1989-09-01), None
patent: WO 01/87920 (2001-11-01), None
Kurt et al., {Reactivities of hydroxyalkyl and bis(hydroxyalkyl) organophosphines, Journal fuer Praktische Chemie (Leipzig) (1970), 312(4), 578-85}.
Kagan et al., {Rabbit gastric lipase in the biocatalytic resolution of 2-hydroxyalkyldiphenylphosphines, Bioorganic & Medicinal Chemistry (1994), 2(1), 15-21}.
Hinton et al., {Abnormal hydrolysis of certain b-(diarylphosphino)propionic esters, Journal of the Chemical Society (1961) 5454-70}.
Issleib et al., {Synthesis of carbethoxyalkylphosphine, Chemische Berichte (1961), 94, 2244-51}.
Santimaria et al., {Rhenium complexes with phosphine-containing peptides. Synthesis and characterization of oxorhenium(V) complexes with N-{N-[3-(diphenylphosphino)propionyl]glycyl}-L-S- benzylcysteine and its methyl ester, J. Chem. Soc., Dalton Trans., 1997, pp. 1765-1771}.
Santimaria et al., {Preparation and characterization of a new rhenium(V) complex containing the 3-diphenylphosphinopropionylglycyl-L-( S-benzyl)-cysteinyl methyl ester ligand, Inorganica Chimica Acta 240 ( 1995 ) 291-297}.
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-lodoazides 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 →4GIcNAcβ-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 and 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 S
Bertozzi Carolyn R.
Saxon Eliana
Borden Paula A.
Bozicevic Field & Francis LLP
Francis Carol L.
Nwaonicha Chukwuma O
Sullivan Daniel M
LandOfFree
Chemoselective ligation does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Chemoselective ligation, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Chemoselective ligation will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2703508