Protecting group for synthesizing oligonucleotide analogs

Details Protecting group for synthesizing oligonucleotide analogs Protecting group for synthesizing oligonucleotide analogs

1997-03-03

1998-06-02

Kunz, Gary L.

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

Organic compounds

Carbohydrates or derivatives

536 245, 536 261, 536 553, C07H 102, C07H 2104, C07H 2102

Patent

active

057602093

ABSTRACT:
Nucleoside analog phosphoramidites are provided in which the 3'-hydroxyl group is protected with an 2-N-amidoethyl group. The 2-N-amidoethyl protected nucleoside analogs are useful in the synthesis of a wide variety of oligonucleotide analogs. Coupling yields with the protected phosphoramidites in solution or solid phase oligonucleotide analog synthesis are high and the 2-N-amidoethyl group can be removed easily under standard conditions.

REFERENCES:
patent: Re34069 (1992-09-01), Koster et al.
patent: 4310662 (1982-01-01), Crea
patent: 4373071 (1983-02-01), Itakura
patent: 4401796 (1983-08-01), Itakura
patent: 4415732 (1983-11-01), Caruthers et al.
patent: 4419509 (1983-12-01), Hsiung
patent: 4458066 (1984-07-01), Caruthers et al.
patent: 4500707 (1985-02-01), Caruthers et al.
patent: 4522735 (1985-06-01), Chaser
patent: 4668777 (1987-05-01), Caruthers et al.
patent: 4689405 (1987-08-01), Frank et al.
patent: 4725677 (1988-02-01), Koster et al.
patent: 4816571 (1989-03-01), Andrus et al.
patent: 4965349 (1990-10-01), Woo et al.
patent: 4973679 (1990-11-01), Caruthers et al.
patent: 5003097 (1991-03-01), Beaucage et al.
patent: 5071974 (1991-12-01), Groody
patent: 5132418 (1992-07-01), Caruthers et al.
patent: 5151510 (1992-09-01), Stec et al.
patent: 5166387 (1992-11-01), Hirschbein
patent: 5218088 (1993-06-01), Gorenstein et al.
patent: 5218103 (1993-06-01), Caruthers et al.
patent: 5252723 (1993-10-01), Bhatt
patent: 5252760 (1993-10-01), Urdea et al.
patent: 5292875 (1994-03-01), Stec et al.
patent: 5310894 (1994-05-01), Zeiger
patent: 5359051 (1994-10-01), Cook et al.
patent: 5359052 (1994-10-01), Stee et al.
patent: 5401837 (1995-03-01), Nelson
patent: 5436327 (1995-07-01), Southern et al.
patent: 5449769 (1995-09-01), Bhatt
patent: 5510239 (1996-04-01), Baracchini, Jr. et al.
patent: 5510476 (1996-04-01), Ravikumar et al.
patent: 5512438 (1996-04-01), Ecker et al.
patent: 5512668 (1996-04-01), Stec et al.
patent: 5514788 (1996-05-01), Bennett et al.
patent: 5514789 (1996-05-01), Kempe
patent: 5523389 (1996-06-01), Ecker et al.
patent: 5571902 (1996-11-01), Ravikumar et al.
patent: 5614621 (1997-03-01), Ravikumar et al.
H.C.P.F. Roelen et al., "A Study On The Use Of Phenylacetyl Disulfide In The Solid-Phase Synthesis Of Oligodeoxynucleoside Phosphorothiotes", Recl. Trav. Chim. Pays-Bas, vol. 110, pp. 325-331, (1991).
George Barany et al., "A General Strategy For Elaboration Of The Dithiocarbonyl Functionality, -(C=O)SS-: Application To The Synthesis Of Bis(Chlorocarbonyl)Disulfane And Related Derivatives Of Thiocarbonic Acids", J. Org. Chem. vol. 48, pp. 4750-4761, (1983).
Mitsuo Kodomari et al., "A Convenient Synthesis Of Bis(Acyl) Disulfides Using Phase-Transfer Catalysis", Synthesis, Aug. (1981), pp. 637-638.
P.C.J. Kamer et al., "An Efficient Approach Toward The Synthesis Of Phosphorothioate Diesters Via The Schonberg Reaction", Tetrahedron Letters, vol. 30, No. 48, pp. 6757-6760, (1989).
Radhakrishnan P. Iyer et al., "A Novel Nucleoside Phosphoramidite Synthon Derived From 1R,2S-Ephedrine", Tetrahedron: Asymmetry, vol. 6, No. 5, pp. 1051-1054, (1995).
Kazunobu Miura et al., "Blockwise Mechanical Synthesis Of Oligonucleotides By The Phosphoramidite Method", Chem. Pharm. Bull, vol. 35, No. 2, pp. 833-836, (1987).
Willi Bannwarth, "Synthesis of Oligodeoxynucleotides By The Phosphite-triester Method Using Dimer Units And Different Phosphorous-Protecting Groups", Helvetica Chimica Acta, vol. 68, pp. 1907-1913, (1985).
G. Kumar et al., "Improvements In Oligodeoxyribonucleotide Synthesis: methyl N,N-Dialkylphosphoramidite Dimer Units For Solid Support Phosphite", J. Org. Chem., vol. 49, pp. 4905-4912, (1984).
Radhakrishnan P. Iyer et al., "Nucleoside Oxazaphospholidines As Novel Synthons in Oligonucleotide Synthesis", J. Org. Chem., vol. 60, No. 17, pp. 5388-5389, (1995).

Affiliated with

Also associated with

Rating

Protecting group for synthesizing oligonucleotide analogs does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Protecting group for synthesizing oligonucleotide analogs, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Protecting group for synthesizing oligonucleotide analogs will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1461344