Polish Academy of Sciences

Applied Biosystems, LLC

Lynx Therapeutics, Inc.

Instytut Immunologii I Terapii Doswiadczalnej Pan

Instytut Przemyslu Farmaceutycznego

Centrum Baden Molekularnych I Makromolekularnych -pan

Polish Academy of Science

Wojciech J Stec

Bogdan Uznanski

Andrzej Grajkowski

Bernard L Hirschbein

B John Bergot

Karen L Fearon

Andrzej Kutner

Wieslaw Szelejewski

Czeslaw Radzikowski

Grzegorz Grynkiewicz

Konrad Misiura

Jacek Grodner

Halina Kusnierczyk

Slawomira Pilichowska

Ryszard Kinas

Karen L Fearson

Methods and compounds are provided for solid phase synthesis of oligonucleotides and related polymers by condensing protected monomer-O-�1,3,2-dichalcogen-substituted-phospholane! synthons in the presence of a catalytic base. Compounds of the invention include 2-N-substituted-1,3,2-dichalcogen-substituted-phospholane precursors of the above synthons, the protected monomer-O-�1,3,2-dichalcogen-substituted-phospholane! synthons, and P-chiral oligonucleotides and related P-chiral polymers.

Oligonucleotides having R.sub.p and S.sub.p linkages at predetermined

Methods and compounds are provided for solid phase synthesis of oligonucleotides and related polymers by condensing protected monomer-O-[1,3,2-dichalcogen-substituted-phospholane] synthons in the presence of a catalytic base. Compounds of the invention include 2-N-substituted-1,3,2-dichalcogen-substituted-phospholane precursors of the above synthons, the protected monomer-O-[1,3,2-dichalcogen-substituted-phospholane] synthons, and P-chiral oligonucleotides and related P-chiral polymers.

Method of making oligonucleotides and oligonucleotide analogs using

Methods and compounds are provided for solid phase synthesis of oligonucleotides and related polymers by condensing protected monomer-O- 1,3,2-dichalcogen-substituted-phospholane! synthons in the presence of a catalytic base. Compounds of the invention include 2-N-substituted-1,3,2-dichalcogen-substituted-phospholane precursors of the above synthons, the protected monomer-O- 1,3,2-dichalcogen-substituted-phospholane! synthons, and P-chiral oligonucleotides and related P-chiral polymers.

Solid phase oligonucleotide synthesis using phospholane intermediates

A method for synthesizing sulfurized oligonucleotide analogs, such as phosphorothioate and phosphorodithioate analogs, is provided that employs a thiophosphorus compound, such as a thiophosphoric, dithiophosphoric, thiophosphinic, or dithiophosphinic acid disulfide or polysulfide, as a sulfurizing agent. The method of the invention may be used to sulfurize any phosphorous(III)containing intermediate. Preferably, the method is practiced on a commercial DNA synthesizer using phosophoramidite and/or phosphorthioamidite intermediates.

Method of synthesizing sulfurized oligonucleotide analogs

A method for synthesizing sulfurized oligonucleotide analogs, such as phosphorothioate and phosphorodithioate analogs, is provided that employs a thiophosphorus compound, such as a thiophosphoric, dithiophosphoric, thiophosphinic, or dithiophosphinic acid disulfide or polysulfide, as a sulfurizing agent. The method of the invention may be used to sulfurize any phosphorous(III)-containing intermediate. Preferably, the method is practiced on a commercial DNA synthesizer using phosphoramidite and/or phosphorthioamidite intermediates.

Method of synethesizing sulfurized oligonucleotide analogs

Process for production of derivatives of 1,3,2-oxazaphosphorinane of general formula 1, ##STR1## wherein R.sub.1 and R.sub.2 represent hydrogen atom or 2-halogenoalkyl group, and R.sub.1 and R.sub.2 are not at the same time hydrogen atoms, and X represents halogen atom is based, according to the invention, on the reduction of the respective 3-halogenoacyl derivatives of 1,3,2-oxazaphosphorinane of general formula 2, ##STR2## wherein the substituents have the above given meaning. The reduction is accomplished with the use of sodium borohydride in the presence of boron trifluoride etherate. Derivatives that are prepared by the procedure described here demonstrate antitumor activity.

Process for the production of 1,3,2-oxazaphosphorinanes

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Lodz, Poland

Wojciech J Stec