Methods and compositions for the tandem synthesis of two or...

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

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C536S027210, C536S119000

Reexamination Certificate

active

07615629

ABSTRACT:
The present invention relates to novel methods and novel solid support materials for the tandem synthesis of two or more different oligonucleotides on the same solid support in one synthetic run. The methods involve novel support preparations comprised of two or more types of orthogonally protected anchor groups. Subsequent to the selective removal of the first of the respective protective groups, the first oligonucleotide is assembled on the deblocked anchor groups according to standard methods, preferably via phosphoramidite chemistry. Following the capping of said first oligonucleotide, the anchor groups blocked by a second type of protective group are selectively liberated and serve as the starting point for the assembly of a second oligonucleotide, and so forth. After completion of all the syntheses on the solid support, the oligonucleotides are released from the solid support and deprotected at the nucleobases, using standard methods. Preparations obtained using the method of this invention, generally contain two or more different oligonucleotides. Such preparations are particularly useful in applications that require pairs of oligonucleotide primers, several probes at a time, duplexed nucleic acid fragments, or other combinations of oligonucleotides that are useful in applications such as PCR, sequencing, multiplexed genotyping, cloning and RNA interference. The invention includes procedures for the preparation of the novel solid supports of the invention.

REFERENCES:
patent: 4291024 (1981-09-01), Turcotte
patent: 4349552 (1982-09-01), Takaya et al.
patent: 4415732 (1983-11-01), Caruthers et al.
patent: 4458066 (1984-07-01), Caruthers et al.
patent: 4616071 (1986-10-01), Holubka
patent: 4725677 (1988-02-01), Koster et al.
patent: 5049656 (1991-09-01), Lewis et al.
patent: 5093232 (1992-03-01), Urdea et al.
patent: 5118800 (1992-06-01), Smith et al.
patent: 5118802 (1992-06-01), Smith et al.
patent: 5200514 (1993-04-01), Chu
patent: 5221736 (1993-06-01), Coolidge et al.
patent: 5393877 (1995-02-01), McLean et al.
patent: 5420276 (1995-05-01), Norbeck
patent: 5464759 (1995-11-01), Coolidge et al.
patent: 5466786 (1995-11-01), Buhr et al.
patent: 5539082 (1996-07-01), Nielsen et al.
patent: 5552535 (1996-09-01), McLean et al.
patent: 5576429 (1996-11-01), Johansson et al.
patent: 5580697 (1996-12-01), Keana et al.
patent: 5869696 (1999-02-01), Reddy et al.
patent: 5874532 (1999-02-01), Pieken et al.
patent: 6090932 (2000-07-01), McGee et al.
patent: 6107479 (2000-08-01), Natt et al.
patent: 6140493 (2000-10-01), Dower et al.
patent: 6171797 (2001-01-01), Perbost
patent: 6262251 (2001-07-01), Pieken et al.
patent: 6368874 (2002-04-01), Gallop et al.
patent: 25 31 257 (1976-01-01), None
patent: 29 31 233 (1981-02-01), None
patent: 0 453 247 (1991-10-01), None
patent: 0 294 196 (1996-03-01), None
patent: 0 982 311 (2000-03-01), None
patent: WO 91/06556 (1991-05-01), None
patent: WO 91/10671 (1991-07-01), None
patent: WO 91/13900 (1991-09-01), None
patent: WO 92/06103 (1992-04-01), None
patent: WO 94/13789 (1994-06-01), None
patent: WO 95/24185 (1995-09-01), None
patent: WO 96/34984 (1996-11-01), None
patent: WO 97/14706 (1997-04-01), None
patent: WO 9741139 (1997-11-01), None
patent: WO 98/30575 (1998-07-01), None
patent: WO 98/30578 (1998-07-01), None
patent: WO 98/47910 (1998-10-01), None
patent: WO 01/84234 (2001-11-01), None
patent: WO 01/96357 (2001-12-01), None
patent: WO/02-16022 (2002-02-01), None
patent: WO 02/20541 (2002-03-01), None
Farcy, et al. “A Pentaerythritol-Based Molecular Scaffold for Solid-Phase Combinatorial Chemistry,” Organic Letters 2001, vol. 3, No. 26, 4299-4301.
Blackwell, et al. “Exploiting Site-Site Interactions on Solid Support to Generate Dimeric Molecules,” Organic Letters 2001, vol. 3, No. 8, pp. 1185-1188.
U.S. Appl. No. 09/845,742, filed May 1, 2001, Pieken et al.
Agrawal and Khorana (May 1972) J. of the American Chem. Society 94(10):3578-3585.
Andrus et al. (1988) Tetrahedron Letters 29:861-864.
Bannwarth and Wippler (1990) Helv. Chim. Acta 73:1139-1147.
Bayer and Mutter (Jun. 1972) Nature 237;512-513.
Beaucage and Iyer (1993) Tetrahedron 49(10):1925-1963.
Blackburn and Guo (1992) Tetrahedron Letters 34(1):149-152.
Duggan and Imagire (Feb. 1989) Synthesis 131-132.
Eadie and Davidson (1987) Nucleic Acid Research 15(20):8333-8349.
Hill et al. (2001) J. Org. Chem. 66:5352-5358.
March, J. ed. (1992) inAdvanced Organic Chemistry839-852.
Natt and Häner (1997) Tetrahedron 53(28):9629-9636.
Rideout and Breslow. (1980) J. Am. Chem. Soc. 102:7816-7817.
Yu et al. (1994) Tetrahedron Letters 35:8565-8568.
Beaucage and Iyer (1992) Tetrahedron 48:2223-2311.
Fischer et al. (1990) BioTechniques 9:300-301.
Gryaznov et al. (1995) Proc. Nat. Acad. Sci. 92:5798-5802.
Hardy et al. (1994) Nucleic Acids Res. 22:2998-3004.
Johnson et al. (1990) BioTechniques 8:424-428.
Kumar and Poonian (1984) J. Org. Chem. 49:4905-12.
McBride and Caruthers (1983) Tetrahedron Letters 24:245-248.
McBride et al. (1988) BioTechniques 6:362-367.
Micklefield (2001) Current Medicinal Chemistry 8:1157-1179.
Ono et al. (1995) Nucleic Acids Res. 23:4677-82.
Reddy et al. (1987) Tetrahedron Letters 28:23-26.
Robles et al. (1995) Nucleic Acids Res. 23:4151-61.
Sinha et al. (1983) Tetrahedron Letters 24:5843-5846.
Aurup et al. (1992) Biochemistry 31:9636-9641.
Bruick et al. (Jan. 1996) Chemistry & Biology 3:49-56.
Bruick et al. (1997) Nucleic Acids Res. 25:1309-1310.
Englisch and Gauss (Jun. 1991) Angew. Chem. Int. Ed. Engl. 30:613-627.
Eritja et al. (1991) Tetrahedron 47: 4113-4120.
Goodchild (May/Jun. 1990) Bioconjugate Chemisty 1:166-187.
Giuliano et al. (1993)J. Org. Chem. 58:4979-4988.
Giuliano et al. (1990)J. Org. Chem. 55:3555-3562.
Haralambidis et al. (1990) Nucleic Acids Res. 18:493-499.
Haralambidis et al. (1987) Tetrahedron Lett. 28:5199-5202.
Huryn and Okabe (1992) Chemical Reviews 92:1745-1768.
Jager et al. (1995)Tetrahedron Letters36:861-864.
Jones et al. (1995) J. Med. Chem. 38:2138-2144.
Juby et al. (1991) Tetrahedron Lett. 32:879-822-882.
Koch et al. (2000) Bioconjugate Chem. 11:474-483.
Koch et al. (1999) Polystyrene or polycarbonate plates/anthraquinone oligos or cDNA with irradiation, Exiqon.
Krieg et al. (1991) Antisense Res. and Dev. 1:161-171.
Leonetti et al. (1990) Bioconjugate Chem. 1:149-153.
Lubineau et al. (1995)Carbohydrate Research270:163-170.
Ludwig and Eckstein (1989) J. Org. Chem. 54:631-635.
Mikhailopulo et al. (1993) Liebigs Ann. Chem. pp. 513-519.
Mori et al. (1989) Nucleosides & Nucleotides 8:649-657.
Nishikubo et al. (1981) Tetrahedron Letters 22:3873-3874.
Roush et al. (1983) Tetrahedron Letters 24:1377-1380.
Schmidt (1994) Synlett 4:241-242.
Shibuya and Ueda (1980) Chem. Pharm. Bull. 28:939-946.
Sinha and Cook (1988) Nucleic Acids Res. 16:2659-2669.
Smith et al. (1987) Methods in Enzymology, 155:260-301.
Sproat et al. (1987) Nucleic Acids Research 15:6181-6188.
Theisen et al. (1992) Tetrahedron Lett. 33:5033-5036.
Tronchet et al. (1990) Tetrahedron Letters 31:531-534.
Tronchet et al. (1988) Nucleosides & Nucleotides 7:249-269.
Tung (1991) Bioconjugate Chem. 2:464-465.
Verheyden et al. (1971) J. Org. Chem. 36:250-254.
Wagner et al. (1991) Nucleic Acids Res. 19:5965-5971.
Warshaw et al. (1990) J. Med. Chem. 33:1663-1666.
Zalipsky (1995) Bioconjugate Chem. 6:150-165.

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

Methods and compositions for the tandem synthesis of two or... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Methods and compositions for the tandem synthesis of two or..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Methods and compositions for the tandem synthesis of two or... will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-4124659

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