Synthesis of sulfurized oligonucleotides

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

Patent

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

536 253, 536 2533, 568 22, C07H 2100, C07H 2102, C07H 2104

Patent

active

06114519&

ABSTRACT:
Methods for the formation of sulfurized oligonucleotides are provided. The methods allow for the formation of phosphorothioate linkages in the oligonucleotides or derivatives, without the need for complex solvent mixtures and repeated washing or solvent changes. Oligonucleotides having from about 8, and up to about 50, nucleotides can be sulfurized according to the methods of the invention with higher yields than have been previously reported.

REFERENCES:
patent: 3923763 (1975-12-01), Edmondson
patent: 4245033 (1981-01-01), Eida et al.
patent: 5264566 (1993-11-01), Froehler et al.
DeBont et al., "Solid-phase synthesis of O-phosphorothioylserine-and -threonine-containing peptides as well as O-phosphoserine-and -threonine-containing peptides", J. Org. Chem., 1993, 58(6), 1309-1317.
Dreef, C.E. et al., "An expeditious synthesis of biologically important myo-inositol phosphorothioates", Bioorg. Med. Chem. Lett., 1991, 1(5), 239-242.
Eckstein, F. (ed.), Oligonucleotides and Analogues, a Practical Approach, Oxford University Press, New York, 1991.
Iyer, R., Beaucage, Serge L. et al., "3H-1,2-benzodithiole-3-one 1,1-dioxide as an improved sulfurizing reagent in the solid-phase synthesis of oligodeoxyribonucleoside phosphorothiioates", J. Am. Chem. Soc., 1990, 112, 1253-1255.
Iyer, R.P. et al., "The Automated Synthesis of Sulfur-Containing Oligodeoxyribonucleotides Using 3H-1,2-Benzodithiol-3-one 1,1-Dioxide as a Sulfur-Transfer Reagent", J. Org. Chem., 1990, 55(15), 4693-4699.
Kamer et al., "An Efficient Approach Toward the Synthesis of Phosphorothioate Diesters Via the Schonberg Reaction", Tetra. Lett., 1989, 30(48), 6757-6760.
Kodomari et al., "A Convenient Synthesis of Bis [acyl] Disulfides using Phase-Transfer Catalysis", Synthesis, 1981, 637-638(Aug. 1981).
Kozikowski, A.P. et al., "Tools for Cell Signaling: Synthesis of the 3-Phosphatase-Resistant 1,3,4,5-InsP4 Mimic, 1D-myo-Inositol 1,4, 5-Trisphosphate 3-Phosphorothioate", J. Org. Chem., 1994, 59(9), 2279-2281.
Lozano, J.I. et al., "Electrosynthesis of 2-benzhydrylidene-4,4-diphenyl-1, 3-oxathiolan-5-one: the reaction pathway", Tetrahedron, 1996, 52(4), 1259-1266.
Roelen et al., "A study on the use of phenylacetyl disulfide in the solid-phase synthesis of oligodeoxynucleoside phosphorothioates", Rech. Trav. Chim. Pays-Bas, 1991, 110, 325-331(Jul.-Aug. 1991).
Wyrzykiewicz, T.K. et al., "Efficiency of sulfurization in the synthesis of oligodeoxyribonucleotide phosphorothioates utilizing various sulfurizing reagents", Bioorg. Med. Chem. Lett., 1994, 4 (12), 1519-1522.
Zhang et al.(I), "Synthesis and Properties of Novel Thiono Triester Modified Antisense Oligodeoxynucleotide Phosphorothioates," Bioorganic & Medicinal Chem. Letters, 5(15), 1735-1740 (Aug. 3, 1995).
Zhang et al. (II), "Thiono Triester Modified Antisense Oligonucleotides for Inhibition of Human Cytomegalovirus In Vitro, " Bioorganic & Medicinal Chem. Letters, 6(16), 1911-1916 (Aug. 20, 1996).
Bokarev et al., "Synthesis of Bis(Alkyl Xanthyl) Trisulfides," Izv. Akad. Nauk SSSR, Ser. Khim., 1964(12), 2175-2182; Chem. Abstr., 62(7), Abstr. No. 7631d (Mar. 29, 1965); only Abstract supplied.
Scholl et al., "Novel Symmetrical and Mixed Carbamoyl and Amino Polysulfanes by Reactions of (Alkoxydichloromethyl)polysulfuranyl Substrates with N-Methylaniline," J. Organic Chem., 51(10), 1866-1881 (1986).
Barany et al., "A General Strategy for Elaboration of the Dithiocarbonyl Functionality, -(C=O)SS-: Application to the Synthesis of Bis(chlorocarbonyl)disulfane and Related Derivatives of Thiocarbonic Acids," J. Organic Chem., 48(24), 4750-4761 (Dec. 2, 1983).
Carey et al., Advanced Organic Chemistry. 3rd Ed., Part A: Structure and Mechanisms, Plenum Press, New York, NY, 1990, only pp. 473-475 supplied.

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Synthesis of sulfurized oligonucleotides does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Synthesis of sulfurized oligonucleotides, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Synthesis of sulfurized oligonucleotides will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-2213462

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.