Purification of synthetic oligomers

Details Purification of synthetic oligomers Purification of synthetic oligomers

2007-10-01

2010-12-14

Tsang, Cecilia (Department: 1654)

Drug, bio-affecting and body treating compositions

Dentifrices

Phosphate compound containing

Reexamination Certificate

active

07850949

ABSTRACT:
This invention provides a novel method for purifying synthetic oligomers comprising capping, polymerizing and separating any failure sequences produced during oligomer synthesis. Either the failure sequence or the full-length oligomer may be polymerized. Optionally, small molecule impurities may also be incorporated into the polymerized material. The invention provides novel capping agents having a polymerizable functional group. The invention also provides kits comprising at least one composition of the present invention.

REFERENCES:
patent: 3712936 (1973-01-01), Jelinek
patent: 6692912 (2004-02-01), Boles et al.
patent: 6921818 (2005-07-01), Sproat
patent: 7125945 (2006-10-01), Shah
patent: 2003/0195351 (2003-10-01), Pieken et al.
patent: 2006/0178507 (2006-08-01), Berry et al.
patent: 03/018616 (2003-03-01), None
patent: 2004/002995 (2004-01-01), None
patent: WO-2004/002995 (2004-01-01), None
patent: WO 2005/035588 (2005-04-01), None
patent: WO-2005/087818 (2005-09-01), None
patent: WO 2006/113792 (2006-10-01), None
patent: 2008/067026 (2008-06-01), None
Adamczyk, M. et al., “Synthesis of biological markers in fossil fuels. 2. Synthesis and 13C NMR studies of substituted indans and tetralins,” J. Org. Chem. (1984) 49:4226-4237.
Atkinson, R.C. et al., “The syntheses and catalytic applications of unsymmetrical ferrocene ligands,” Chem. Soc. Rev. (2004) 33:313-328.
Banfield, S.C. et al., “Unexpected reactivity of the Burgess reagent with thiols: synthesis of symmetrical disulfides,” J. Org. Chem. (2007) 72(13):4989-4992.
Bondinell, W.E. et al., “Inhibitors of phenylethanolamine N-methyltransferase and epinephrine biosynthesis. 1. Chloro-substituted 1,2,3,4-tetrahydroisoquinolines,” J. Med. Chem. (1980) 23:506-511.
Burgler. F.W. et al., “Stereoselective addition reactions with chalcogen electrophiles,” Archive for Org. Chem. (2007) x:21-28.
Colacot, T.J., “A concise update on the applications of chiral ferrocenyl phosphines in homogeneous catalysis leading to organic synthesis,” Chem. Rev. (2003) 103:3101-3118.
Crooke, S.T., “Progress in antisense technology,” Annu. Rev. Med. (2004) 55:61-95.
Curnow, O.J. et al., “Synthesis, structures and raclmeso isomerization behaviour of bisplanar chiral bis(phosphino-η5-indenyl)iron(II) complexes,” J. Organomet. Chem. (2004) 689:1897-1910.
Curnow, O.J. et al., “Facile meso to rac isomerization of the bis-planar chiral ferrocenyldiphosphine bis(1-(diphenylphosphino)-η5-indenyl)iron(II),” Organometallics (2002) 21:2827-2829.
Curnow, O.J. et al., “Mechanistic studies on a facile ring-flipping process in planar chiral ferrocenes under ambient and high pressure and its relevance to asymmetric catalysis,” Organometallics (2004) 23:906-912.
Dai, L.X. et al., “Assymmetric catalysis with chiral ferrocene ligands,” Acc. Chem. Res. (2003) 36:659-667.
Fang, S. et al., “Fluoride-cleavable biotinylation phosphoramidite for 5′-end-labeling and affinity purification of synthetic oligonucleotides,” Nuc. Acids Res. (2003) 31(2):708-715.
Fang, S. et al., “Reversible 5′-end biotinylation and affinity purification of synthetic RNA,” Tetrahedron Letters (2004) 45:7987-7990.
Fang, S. et al., “Reversible biotinylation of the 5′-terminus of ligodeoxyribonucleotides and its application in affinity purification,” Curr. Protocols in Nucleic Acid Chem. (2003) 4.20.1-4.20.17.
Fang, S. et al., “Reversible biotinylation phosphoramidite for 5′-end-labeling, phosphorylation, and affinity purification of synthetic oligonucleotides,” Bioconjugate Chem. (2003) 14:80-85.
Farrugia, L.J., “ORTEP-3 for Windows—a version of ORTEP-III with a graphical user interface (GUI),” J. Appl. Cryst. (1997) 30:565.
Fu, G.C., “Asymmetric catalysis with ‘planar-chiral’ derivatives of 4-(dimethylamino)pyridine,” Acc. Chem. Res. (2004) 37:542-547.
Gong, J-X. et al., “Total synthesis of gymnorrhizol, an unprecedented 15-membered macrocyclic polydisulfide from the Chinese mangrove Bruguiera gymnorrhiza,” J. Org. Lett. (2007) 9(9):1715-1716.
Hajipour, A.R. et al., “Oxidation of thiols with methyltriphenylphosphonium dichromate (MTPPD) in dichloromethane at room temperature,” J. Sulfur Chem. (2006) 27(5):441-444.
Hauser, F.M. et al., “Ketone transposition: 2(1H)-tetralones from 1(2H)-tetralones,” Synthesis-Stuttgart (1980) 621-623.
Imanishi, T. et al., “BNAs: novel nucleic acid analogs with a bridged sugar moiety,” Chem. Commun. (2002) 1653-1659.
Ishikawa, F. et al., “Cyclic guanidines. XVI. Synthesis and biological activities of tetracyclic imidazo[2,1-b]quinazolinine derivatives,” Chem. & Pharm. Bull. (1985) 33:3336-3348.
Ma, H.C. et al., “Synthesis of iminoquinones from anilines using IBX in DMSO,” Synthesis (2007) 3:412-416.
Maier, T.C. et al., “Catalytic enantioselective O-H insertion reactions,” J. Am. Chem. Soc. (2006) 128:4594-4595.
Olejnik, J. et al., “Photocleavable biotin phosphoramidite for 5′-end-labeling, affinity purification and phosphorylation of synthetic oligonucleotides,” Nuc. Acids Res. (1996) 24(2):361-366.
Pearson, W.H. et al., “Fluorous affinity purification of oligonucleotides,” J. Org. Chem. (2005) 70:7114-7122.
Ruble, J.C. et al., “Chiral π-complexes of heterocycles with transition metals: a versatile new family of nucleophilic catalysts,” J. Org. Chem. (1996) 61:7230-7231.
Sathe, M. et al., “Oxidation of thiols to disulfides using silica chloride as heterogeneous catalyst,” Chemistry Letters (2006) 35(9):1048-1049.
Schulte, M. et al., “Purification of DMT-on oligonucleotide by simulated moving-bed (SMB) chromatography,” Org. Process Res & Dev. (2005) 9:212-215.
Shintani, R. et al., “Copper-catalyzed enantioselective conjugate addition of diethylzinc to acyclic enones in the presence of planar-chiral phosphaferrocene-oxazoline ligands,” Org. Lett. (2002) 4:3699-3702.
Siemeling, U. et al., “1,1′-di(heteroatom)-functionalised ferrocenes as [N,N], [O,O] and [S,S] chelate ligands in transition metal chemistry,” Chem. Soc. Rev. (2005) 34:584-594.
Sobik, P. et al., “Identification, synthesis, and conformation of tri- and tetrathiacycloalkanes from marine bacteria,” J. Org. Chem. (2007) 72(10):3776-3782.
Sproat, B.S. et al., “Fast and simple purification of chemically modified hammerhead ribozymes using a lipophilic capture tag,” Nuc. Acids Res. (1999) 27(8):1950-1955.
Trost, B.M. et al., “Asymmetric transition-metal-catalyzed allylic alkylations: applications in total synthesis,” Chem. Rev. (2003) 103:2921-2943.
Trost, B.M., “Asymmetric catalysis an enabling science,” Proc. Natl. Acad. Sci. USA (2004) 101:5348-5355.
Vester, B. et al., “LNC (Locked Nucleic Acid): High-affinity targeting of complementary RNA and DNA,” Biochem. (2004) 43(42):13233-13241.
Wilson, C. et al., “Building oligonucleotide therapeutics using non-natural chemistries,” Curr. Opin. Chem. Biol. (2006) 10:607-614.
Yavari, I. et al., “Conversion of thiols to disulfides using a hexamethylenetetramine-bromine complex,” Phosphorus, Sulfur and Silicon and the Related Elements, (2006) 181(11):2659-2662.
Fang, S., “Simple methods for oligonucleotide purification,” National Science Foundation Award Abstract #0647129 (2007) 2 pages—Retrieved from the Internet: http://www.nsf.gov/awardsearch/showaward.do?awardnumber=0647129, retrieved on May 6, 2008.
International Search Report and Written Opinion of the International Searching Authority for Application No. PCT/US2007/080099 dated May 8, 2008 (12 pages).

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