Method of synthesizing oligonucleotides labeled with ammonia-lab

Details Method of synthesizing oligonucleotides labeled with ammonia-lab Method of synthesizing oligonucleotides labeled with ammonia-lab

Filed on

1987-12-24

Date issued

1990-10-23

Examiner

Rollins, John W.

Patent Class

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

SubClass

Organic compounds

SubSubClass

Carbohydrates or derivatives

Other Related Categories

536 28, 536 29, C07H 1900

Type

Patent

Status

active

Patent number

049653490

Description

ABSTRACT:
The invention provides a novel cleavage reagent for hydrolysing base-labile linking groups between a solid phase support and oligonucleotides. The cleavage reagent comprises a lower alkyl alcohol, water, and a non-nuccleophilic hindered alkylamine containing from 3 to 6 carbon atoms in a ratio of about 1:1:1 to about 1:3:1, respectively. An important property of the cleavage reagent is that it preserves the fluorescent characteristics of rhodamine dyes during cleavage, thereby making it possible to completely synthesize rhodamine-labeled oligonucleotides by solid phase methods. Rhodamine phosphoramidites are provided to further enhance the efficiency of synthesizing rhodamine-labeled oligonucleotides by such methods.

REFERENCES:
patent: 4659774 (1987-04-01), Webb et al.
Agrawal et al., "Efficient Methods for Attaching Non--Radioactive Labels to the 5' Ends of Synthetic Oligodeoxyribonucleotides", Nucleic Acids Research, vol. 14, No. 15 (1986), pp. 6227-6245.
McBride et al., "Amidine Protecting Groups for Oligonucleotide Synthesis", J. Am. Chem. Soc., V108, pp. 2040-2048.
Dazeley, Organic Chemistry, p. 153, (Cambridge Univ. Press, 1969).
Gait, in Hodge et al., Eds., Chapter 9, Polymer--Supported Reactions in Organic Synthesis (John Wiley & Sons, New York, 1980).
Amarnath et al., Chemical Reviews, vol. 77, pp. 183-217 (1977).

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