Methods for H-phosphonate synthesis of mono- and oligonucleotide

Details Methods for H-phosphonate synthesis of mono- and oligonucleotide Methods for H-phosphonate synthesis of mono- and oligonucleotide

1995-10-20

1998-01-06

Kunz, Gary L.

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

Organic compounds

Carbohydrates or derivatives

536 253, C07H 102, C07H 2104

Patent

active

057056293

ABSTRACT:
New methods of synthesizing mono- and oligo- nucleotide H-phosphonates are disclosed. The methods comprise contacting a mononucleoside with phosphonic acid and benzoyl anyhydride to yield the corresponding mononucleoside H-phosphonate. Preferrably a catalytic amount of triphosgene is also used. A similar procedure can be used to couple a first mononucleoside to a second mononucleoside or to an oligonucleotide, the method comprising contacting, in the presence of benzoic anhydride and, preferrably, a catalytic amount of triphosgene, a mononucleotide or oligonucleotide having a free 5' hydroxyl with a mononucleoside having a 3' hydroxyl-bearing phosphorous moiety (preferably H-phosphonate).

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