Solid support reagents for the direct synthesis of 3'-labeled po

Details Solid support reagents for the direct synthesis of 3'-labeled po Solid support reagents for the direct synthesis of 3'-labeled po

1996-01-29

1998-04-07

Marschel, Ardin H.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

435 6, 435810, 436501, 536 221, 536 231, 536 241, 536 243, 536 2431, 536 2432, 536 2433, 935 77, 935 78, C07H 2100

Patent

active

057366268

ABSTRACT:
The compounds of the invention are exemplified by the class of diglycolate synthesis supports particularly useful as support reagents for the direct synthesis of 3'-labeled polynucleotides. Generally, the compounds of the invention have the structure ##STR1## where T is an acid-cleavable hydroxyl protecting group, e.g., 4,4'-dimethoxytrityl; L.sub.1 is a linker for connecting a 3'-terminal nitrogen to carbon; L.sub.2 and L.sub.3 are linkers for connecting oxygen and carbon; W is a solid support, e.g., CPG or polystyrene; L.sub.4 is a linker for connecting the solid support to nitrogen; R.sub.1 and R.sub.2 are nitrogen substituents, e.g., hydrogen, lower alkyl, nitrogen protecting group, or label; and R.sub.3 through R.sub.7 are carbon substituents, e.g., hydrogen or lower alkyl. In a first particularly preferred embodiment, the synthesis supports of the invention are exemplified by compounds having the structure ##STR2## where DMT is 4,4'-dimethoxytrityl and W is polystyrene. In a second particularly preferred embodiment, the synthesis supports of the invention are exemplified by compounds having the structure ##STR3## where DMT and W are defined above.

REFERENCES:
patent: 5141813 (1992-08-01), Nelson
patent: 5231191 (1993-07-01), Woo et al.
patent: 5401837 (1995-03-01), Nelosn
Lee et al. Nucleic Acids Research, 21(16): 3761-3766 (1993) Allecic Discrimination by nick-translation PCR with fluorogenic probes.
Holland et al. Proc. Natl. Acad. Sci., 88: 7276-7280 Detection of specific polymerase chain by utilizing the 5'.fwdarw.3'exonuclease activity of the Thermus aquaticus DNA polymerase.
Livak et al. PCR Methods and Applications, 4:357-362, Cold Spring Harbor Laboratory Press, 1995 Oligonucleotides with Fluorescent Dyes at Opposite Ends Provide a Quenched Probe System Useful for Detection PCR Product and Nucleic Acid Hybridization.
Nelson et al. Nucleic Acids Research, 20(23): 6253-6259 (1992) Oligonucleotide labeling methods 3. Direct labeling of oligonucleotides employing a novel, non-nucleosidic, 2-aminobutyl-1, 3-propanediol backbone.
Gryaznov et al. Tetrahedron Letters, 34(8): 1261-1264 (1993) Anchor for One Step Release of 3'-Aminooligonucleotides from a Solid Support.
Peninsula Laboratories, Inc. Peninsula Laboratories, Inc. 1994-1995 Catalog, pp. 238-240, Belmont, California Chemical compound structure for: Rhodamine-CEP; DMT-5-Rhodamine-dU-CEP; DMT-Rhodamine-CPG.
Clontech Laboratories, Inc. Clontech 1994-1995 Catalog, Tools for the Molecular Biologist, pp. 113-124, Palo Alto, California Label-On Reagents; Aminomodifiers; Special Modification Reagents.

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