Title:
RNA SYNTHESIS - PHOSPHORAMIDITES FOR SYNTHETIC RNA IN THE REVERSE DIRECTION, AND APPLICATION IN CONVENIENT INTRODUCTION OF LIGANDS, CHROMOPHORES AND MODIFICATIONS OF SYNTHETIC RNA AT THE 3' - END
Document Type and Number:
WIPO Patent Application WO/2010/027512
Kind Code:
A3
Abstract:
The present invention relates to novel phosphoramidites, A-n-bz, C-n-bz, C-n-ac, G-n-ac and U are produced with an HPLC purity of greater than 98% and 31P NMR purity greater than 99%. A novel process of reverse 5'→ 3' directed synthesis of RNA oligomers has been developed and disclosed. Using that method demonstrated high quality RNA synthesis with coupling efficiency approaching 99%.
Inventors:
SRIVASTAVA SURESH C (US)
PANDEY DIVYA (IN)
SRIVASTAVA NAVEEN P (US)
BAJPAI SATYA P (IN)
PANDEY DIVYA (IN)
SRIVASTAVA NAVEEN P (US)
BAJPAI SATYA P (IN)
Application Number:
PCT/US2009/005063
Publication Date:
June 10, 2010
Filing Date:
September 08, 2009
Export Citation:
Assignee:
CHEMGENES CORP (US)
SRIVASTAVA SURESH C (US)
PANDEY DIVYA (IN)
SRIVASTAVA NAVEEN P (US)
BAJPAI SATYA P (IN)
SRIVASTAVA SURESH C (US)
PANDEY DIVYA (IN)
SRIVASTAVA NAVEEN P (US)
BAJPAI SATYA P (IN)
International Classes:
C07H21/02; C07H19/067; C07H19/167
Other References:
THOMAS WAGNER, WOLFGANG PFLEIDERER: "Nucleotides, Part LXV , Synthesis of 2'-Deoxyribonucleoside 5'-Phosphoramidites: New Building Blocks for the Inverse (5'-3')-Oligonucleotide Approach", HELVETICA CHIMICA ACTA, vol. 83, no. 8, 15 August 2000 (2000-08-15), pages 2023 - 2035, XP002569710, ISSN: 0018-019X
MATYSIAK S ET AL: "Acetal oligonucleotide conjugates in antisense strategy", NUCLEOSIDES & NUCLEOTIDES, MARCEL DEKKER, INC, US, vol. 16, 1 January 1997 (1997-01-01), pages 855 - 861, XP002244702, ISSN: 0732-8311
SCHWARTZ M E ET AL: "A Universal Adapter for Chemical Synthesis of DNA or RNA on any Single Type of Solid Support", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, NL, vol. 36, no. 1, 2 January 1995 (1995-01-02), pages 27 - 30, XP004028936, ISSN: 0040-4039
RAVIKUMAR, VASULINGA T. ET AL: "Stereoselective Synthesis of Alkyl-Phosphonates: A Facile Rearrangement of Cyanoethyl-Protected Nucleoside Phosphoramidites", ORGANIC PROCESS RESEARCH & DEVELOPMENT, vol. 8, no. 4, 22 May 2004 (2004-05-22), pages 603 - 608, XP002569711, ISSN: 1083-6160
SRIVASTAVA, SURESH C. ET AL: "RNA synthesis: phosphoramidites for RNA synthesis in the reverse direction. Highly efficient synthesis and application to convenient introduction of ligands, chromophores and modifications of synthetic RNA at the 3'-end", NUCLEIC ACIDS SYMPOSIUM SERIES, vol. 52, no. 1, 8 September 2008 (2008-09-08), pages 103 - 104, XP002569712, ISSN: 1746-8272
MATYSIAK S ET AL: "Acetal oligonucleotide conjugates in antisense strategy", NUCLEOSIDES & NUCLEOTIDES, MARCEL DEKKER, INC, US, vol. 16, 1 January 1997 (1997-01-01), pages 855 - 861, XP002244702, ISSN: 0732-8311
SCHWARTZ M E ET AL: "A Universal Adapter for Chemical Synthesis of DNA or RNA on any Single Type of Solid Support", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, NL, vol. 36, no. 1, 2 January 1995 (1995-01-02), pages 27 - 30, XP004028936, ISSN: 0040-4039
RAVIKUMAR, VASULINGA T. ET AL: "Stereoselective Synthesis of Alkyl-Phosphonates: A Facile Rearrangement of Cyanoethyl-Protected Nucleoside Phosphoramidites", ORGANIC PROCESS RESEARCH & DEVELOPMENT, vol. 8, no. 4, 22 May 2004 (2004-05-22), pages 603 - 608, XP002569711, ISSN: 1083-6160
SRIVASTAVA, SURESH C. ET AL: "RNA synthesis: phosphoramidites for RNA synthesis in the reverse direction. Highly efficient synthesis and application to convenient introduction of ligands, chromophores and modifications of synthetic RNA at the 3'-end", NUCLEIC ACIDS SYMPOSIUM SERIES, vol. 52, no. 1, 8 September 2008 (2008-09-08), pages 103 - 104, XP002569712, ISSN: 1746-8272
Attorney, Agent or Firm:
CARROLL, Alice, O. et al. (Brook Smith & Reynolds, P.C.,530 Virginia Road, P.O. Box 913, Concord MA, US)
Download PDF:
Previous Patent: CLOSED LOOP SCROLL EXPANDER ENGINE
Next Patent: METHODS FOR KILLING PSMA-EXPRESSING, TAXANE-RESISTANT CANCER CELLS
Next Patent: METHODS FOR KILLING PSMA-EXPRESSING, TAXANE-RESISTANT CANCER CELLS