Orthoester protecting groups in RNA synthesis

Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives

Patent

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

536 253, 536 261, C07H 100, C07H 102, C07H 2102

Patent

active

058891366

ABSTRACT:
Phosphoramidite oligonucleotide synthesis is facilitated by the use of fluoride-labile 5' silyl protecting groups. RNA synthesis is improved by the use of 2' orthoester protecting groups. Reactions are conducted on a solid phase support, and acidic deprotection conditions are avoided, as is the necessity of oxidizing the phosphite linkage between each coupling reaction.

REFERENCES:
patent: 4415732 (1983-11-01), Caruthers et al.
patent: 4458066 (1984-07-01), Caruthers et al.
"Anhydrous Tert-Butyl Hydroperoxide in Toluene: The Preferred Reagent for Application Requiring Dry TBHP," J. Gordon Hill et al., J. Org. Chem., 48:3607-3608 (1983). Month not available.
"Cyclic Orthoester Functions as New Protecting Groups in Nucleosides," Mitsuo Sekine et al., J. Am Chem. Soc., 105:2044-2049 (1983). Month not available.
"Incompatibility of Acid-Labile 2' and 5' and Protecting Groups for Solid-Phase Synthesis of Oligoribonucleotides," Chris Christodoulou et al., Tetrahedron Letters, 27(13):1521-1522 (1986). Month not available.
"N-Phenoxyacetylated Guanosine and Adenosine Phosphoramidites in the Solid Phase Synthesis of Oligoribonucleotides: Synthesis of a Ribozyme Sequence," Taifeng Wu et al., Tetrahedron Letters, 29(34):4249-4252 (1988). Month not available.
"Prevention of Chain Cleavage in the Chemical Synthesis of 2'-Silylated Oligoribonucleotides," Taifeng Wu et al., Nucleic Acids Research 17(9):3501-3517 (1989). Month not available.
"Solid Phase Synthesis of Oligoribonucleotides Using O-Nitrobenzyl Protection of 2'-Hydroxyl via a Phosphite Triester Approach," Toshiki Tanaka et al., Nucleic Acids Research 14(15):6265-6279 (1986). Month not available.
"Synthesis and NMR Study of Ribooligonucleotides Forming a Hammerhead-type RNA Enzyme System," Osamu Odai et al., Nucleic Acids Research 18(20):5955-5960 (1990). Month not available.
"Synthesis and Properties of Non-Hammerhead RNA Using 1-(2-Chloroethoxy)-Ethyl Group for the Protection of 2'-Hydroxyl Function," Osamu Sakatsume et al., Nucleoside & Nucleotides, 10(1-3):141-153 (1991). Month not available.
"Advances in the Synthesis of Oligonucleotides by the Phosphoramidite Approach," Serge L. Beaucage et al., Tetrahedron 48(12):2223-2311 (1992). Month not available.
"Tetraisopropyldisiloxane-1,3-diyl, a Group for Simultaneous Protection of 3'- and 5'-Hydroxy Functions of Nucleosides," Wojciech T. Markiewicz, J. Chem. Research, (S):24-25 (1979). Month not available.
"2-Chloroethyl Orthoformate as a Reagent for Protection in Nucleotides Synthesis," Tsujiaki Hata et al., Tetrahedron Letters 51:4443-4446 (1969). Month not available.
"Use of the 1-(2-Fluorophenyl)-4-methoxypiperidin-4-yl (Fpmp) Protecting Group in the Solid-Phase Synthesis of Oligo- and Poly-ribonucleotides," M. Vaman Rao et al., J. Chem. Soc. Perkin Trans., Paper 2:43-55 (1993). Month not available.
"Use of the 1-(2-Fluorophenyl)-4-methoxypiperidin-4-yl (Fpmp) and related protecting group in Oligoribonucleotide Synthesis: Stability of Internucleotide Linkages to Aqueous Acid," Daniel C. Capaldi et al., Nucleic Acids Research, 22(12):2209-2216 (1994). Month not available.
"Chemical Synthesis of Biologically Active Oligoribonucleotides Using .beta.-cyanoethyl Protected Ribonucleoside Phosphoramidites," Stephen A. Scaringe et al., Nucleic Acids Research 18(18):5433-5441 (1990). Month not available.
Resmini et al. Helvetica Chimica Acta vol. 76, pp. 158-167, 1993. Month not available.

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Orthoester protecting groups in RNA synthesis does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Orthoester protecting groups in RNA synthesis, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Orthoester protecting groups in RNA synthesis will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-1216177

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.