Method of attaching a fluorescent label to an oligonucleotide

Details Method of attaching a fluorescent label to an oligonucleotide Method of attaching a fluorescent label to an oligonucleotide

1996-06-25

1998-02-24

Marschel, Ardin H.

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

Organic compounds

Carbohydrates or derivatives

536266, 544 14, 544 32, 549220, 549223, 549225, C07H 2100, C07H 1904, C07D27900, C07F 906

Patent

active

057213550

ABSTRACT:
Compounds useful to attach a fluorescein label to an oligonucleotide are disclosed. To create these compounds, oxygen groups on the fluorescein moiety are protected (e.g. with acyl groups). One then links a phosphoramidite to the fluorescein moiety via an amide or thiourea linkage to an active site on the fluorescein ring. The resulting compound can then be directly linked to an oligonucleotide as it is being formed in an automated synthesizer and then deprotected using the same deprotection conditions as are used to deprotect the oligonucleotides. Such compounds are, inter alia, useful to create labelled primers for DNA sequencing.

REFERENCES:
patent: 4762779 (1988-08-01), Snitman
Trainor, et al., "Chemical Reagents for Molecular Biology", Apr. 6, 1989 (Abstract).
Cohen, et al., "Use of phosphoramidite-linked acridine for fluorescent tagging of oligo-deoxy-nucleotides", Derwent World Patents Index Accession No. 89-129850/17 (1989).
"TFA Aminolinker Amidite", Pharmacia LKB Biotechnology advertisement (Nov., 1990).
"AutoPrimer Synthesis Kit Instructions", booklet from Pharmacia LKB Biotechnology (1990).
Haugland, Handbook of Fluorescent Probes and Research Chemicals, pp. 30-32, 34-36 (1989).
Smith, et al., Nature 321:674-679 (1986).
Ansorge, et al., J. Biochem. & Biophys. Meth. 13:315-323 (1986).
Abstracts of Papers (Part 1), Abstract No. 35, 203rd American Chemical Society National Meeting, Apr. 1992.
Millipore Product Bulletin for FluoreDite, May 1993.
P. 118 from 1993-94, Applied Biosystems catalog showing FAM Amidite.

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