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Title:
SYNTHESIS OF DEUTERATED RIBO NUCLEOSIDES, N-PROTECTED PHOSPHORAMIDITES, AND OLIGONUCLEOTIDES
Document Type and Number:
WIPO Patent Application WO/2014/022563
Kind Code:
A3
Abstract:
The present invention is directed towards the synthesis of high purity deuterated sugars, deuterated phosphoramidites, deuterated nucleobases, deuterated nucleosides, deuterated oligonucleotides, and deuterated RNA's of defined sequences which can exhibit biochemically useful and biologically valuable properties, thus having potential for therapeutic uses.

Inventors:
SRIVASTAVA, Suresh, C. (7 Donald Road, Burlington, MA, 01803, US)
YASKO, Amy (184 Bird Hill Road, Bethel, ME, 04217, US)
Application Number:
US2013/053028
Publication Date:
March 27, 2014
Filing Date:
July 31, 2013
Export Citation:
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Assignee:
ASED, LLC (184 Bird Hill Road, Bethel, ME, 04217, US)
International Classes:
C07H19/067; C07B59/00; C07H19/167
Foreign References:
US20020120129A12002-08-29
Other References:
INSIL KIM ET AL: "Interactions of a didomain fragment of the Drosophila Sex-lethal protein with single-stranded uridine-rich oligoribonucleotides derived from the transformer and Sex-lethal messenger RNA precursors: NMR with residue-selective [5- 2 H]uridine substitutions", JOURNAL OF BIOMOLECULAR NMR, vol. 17, 1 January 2000 (2000-01-01), pages 153 - 165, XP055097335
MARINO J. E. RESENDIZ ET AL: "Direct Strand Scission in Double Stranded RNA via a C5-Pyrimidine Radical", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 134, no. 8, 29 February 2012 (2012-02-29), pages 3917 - 3924, XP055097301, ISSN: 0002-7863, DOI: 10.1021/ja300044e
AARON C. JACOBS ET AL: "Direct Strand Scission from a Nucleobase Radical in RNA", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 132, no. 11, 24 March 2010 (2010-03-24), pages 3668 - 3669, XP055097296, ISSN: 0002-7863, DOI: 10.1021/ja100281x
DEVESH KHARE AND JOHN ORBAN: "Synthesis of backbone deuterium labelled [r(CGCGAAUUCGCG)]2 and HPLC purification of synthetic RNA", NUCLEIC ACIDS RESEARCH,, vol. 20, no. 19, 1 January 1992 (1992-01-01), pages 5131 - 5136, XP009175627
LUKIN M A ET AL: "Stereoselective 5'-Monodeuterated Ribonucleoside Phosphoramites as Tools for Conformational Studies of RNA by the NMR Approach", NUCLEOSIDES & NUCLEOTIDES, MARCEL DEKKER INC, US, vol. 18, no. 6-7, 1 January 1999 (1999-01-01), pages 1255 - 1256, XP009175623, ISSN: 0732-8311
MATTHEW H. LYTTLE ET AL: "New nucleoside phosphoramidites and coupling protocols for solid-phase RNA synthesis", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 56, no. 15, 1 July 1991 (1991-07-01), pages 4608 - 4615, XP055097229, ISSN: 0022-3263, DOI: 10.1021/jo00015a010
GUNZENHAUSER S ET AL: "Tetraethylene Glycol-Derived Spacer for Oligonucleotide Synthesis", TETRAHEDRON LETTERS, PERGAMON, GB, vol. 39, no. 35, 27 August 1998 (1998-08-27), pages 6277 - 6280, XP004128847, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(98)01348-3
COLIN B. REESE: "Oligo- and poly-nucleotides: 50 years of chemical synthesis", ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 3, no. 21, 1 January 2005 (2005-01-01), pages 3851, XP055097315, ISSN: 1477-0520, DOI: 10.1039/b510458k
PON R T ED - SUDHIR AGRAWAL: "Solid-Phase Supports for Oligonucleotide Synthesis", 1 January 1993, PROTOCOLS FOR OLIGONUCLEOTIDES AND ANALOGS. SYNTHESIS AND PROPERTIES; [METHODS IN MOLECULAR BIOLOGY], TOTOWA, NJ : HUMANA PRESS, PAGE(S) 465 - 496, ISBN: 978-0-89603-247-7, XP009175601
H T PATHAK ET AL: "SYNTHESIS OF 2'-DEOXY-2'(S)-DEUTBRIO AND 2'-DEOXY-2'(R)_DEUTERIO- B-D-NUCLEOSIDES", PNNTED IN GREAT BNLAM. 004&4020@6 SS.OO+ .OO PERGAMON JOURNALS LTD, 1 January 1986 (1986-01-01), XP055097362, Retrieved from the Internet [retrieved on 20140120]
J-C H WU: "REGIOSPECIFIC SYNTHESIS OF 2'-DEOXY-2',2"-DIDEUTERIO NUCLEOSIDES", TETRAHEDRON, vol. 43, 1 January 1987 (1987-01-01), pages 2355 - 2368, XP055097364
T. PATHAK ET AL: "A regio and stereoselective synthesis of 2',2',3',4'-tetradeuterio-2'-deoxy nucleosides", TETRAHEDRON, vol. 43, no. 18, 1 January 1987 (1987-01-01), pages 4227 - 4234, XP055097365, ISSN: 0040-4020, DOI: 10.1016/S0040-4020(01)83465-7
FOSTER A B: "Deuterium isotope effects in the metabolism of drugs and xenobiotics: implications for drug design", ADVANCES IN DRUG RESEARCH, ACADEMIC PRESS, LONDON, GB, vol. 14, 1 January 1985 (1985-01-01), pages 1 - 40, XP009086953, ISSN: 0065-2490
Attorney, Agent or Firm:
SLAVIN, Michael, A. et al. (McHale & Slavin, P.A.2855 PGA Boulevar, Palm Beach Gardens FL, 33410, US)
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