Title:
METHOD FOR REMOVAL OF NUCLEIC ACID-PROTECTING GROUP
Document Type and Number:
WIPO Patent Application WO/2007/097447
Kind Code:
A1
Abstract:
The object is to provide, in a ribonucleic acid derivative having a substituent represented by the formula (I) which protects a 2'-hydroxyl group in the ribose moiety and silicon protecting groups which protect a 3'-hydroxyl group and a 5'-hydroxyl group in the ribose moiety, a method for removal of the silicon protecting groups from the derivative at low cost, on a large scale, and with good efficiency. (I) wherein WG1 represents an electron-withdrawing group. The method comprises reacting a ribonucleic acid derivative represented by the general formula (1) with a salt between a tertiary amine represented by the general formula (2) and hydrofluoric acid or a mixture of the tertiary amine and hydrofluoric acid to remove silicon protecting groups which protect a 3'-hydroxyl group and a 5'-hydroxyl group in the ribose moiety of the ribonucleic acid derivative, thereby producing a ribonucleic acid derivative represented by the general formula (3).
Inventors:
KITAGAWA HIDETOSHI (JP)
MASUDA HIROFUMI (JP)
MASUDA HIROFUMI (JP)
Application Number:
PCT/JP2007/053492
Publication Date:
August 30, 2007
Filing Date:
February 26, 2007
Export Citation:
Assignee:
NIPPON SHINYAKU CO LTD (JP)
KITAGAWA HIDETOSHI (JP)
MASUDA HIROFUMI (JP)
KITAGAWA HIDETOSHI (JP)
MASUDA HIROFUMI (JP)
International Classes:
C07H19/067; C07H19/10; C07H19/167; C07H19/20; C07H21/02; C07H21/04
Domestic Patent References:
| WO2006022323A1 | 2006-03-02 | |||
| WO2006102970A2 | 2006-10-05 | |||
| WO2005023828A1 | 2005-03-17 |
Other References:
DATABASE CASREACT [online] SANDBRINK J. ET AL.: "Investigation of potential RNA bulge stabilizing elements", XP003017303, accession no. STN Database accession no. (144:326428)
GREENE T.W. ET AL.: "PROTECTIVE GROUPS IN ORGANIC SYNTHESIS", vol. 3RD ED., 1999, JOHN WILEY & SONS, INC., pages: 237 - 241, XP003017304
SANEYOSHI H. ET AL.: "A General Method for the Synthesis of 2'-O-Cyanoethylated Oligoribonucleotides Having Promising Hybridization Affinity for DNA and RNA and Enhanced Nuclease Resistance", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 70, no. 25, 2005, pages 10453 - 10460, XP003017305
DATABASE CAPLUS [online] OHGI T. ET AL.: "A New RNA Synthetic Method with a 2'-O-(2-Cyanoethoxymethyl) Protecting Group", XP003017306, accession no. STN Database accession no. (2005:582219)
WU X. ET AL.: "Synthesis of 5'-C- and 2'-O-(Bromoalkyl)-Substituted Ribonucleotide Phosphoramidites of the Post-synthetic Functionalization of Oligonucleotides on Solid Support", HELVETICA CHIMICA ACTA, vol. 83, no. 6, 2000, pages 1127 - 1144, XP003009347
ITO T. ET AL.: "(Methoxyethoxy)methyl Group: New Amide and Hydroxyl Protecting Group of Uridine in Oligonucleotide Synthesis", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 51, no. 6, 1986, pages 931 - 933, XP002979646
OHGI ET AL., ORGANIC LETTERS, vol. 7, 2005, pages 3477
TAKESHI WADA, BIO INDUSTRY, vol. 21, no. 1, 2004, pages 17
UMEMOTO ET AL., TETRAHEDRON LETTERS, vol. 45, 2004, pages 9529
HISAO SANEYOSHI ET AL., JOURNAL OF ORGANIC CHEMISTRY, vol. 70, 2005, pages 10453
JOURNAL OF MOLECULAR STRUCTURE, vol. 193, 1989, pages 247
POLISH JOURNAL OF CHEMISTRY, vol. 67, no. 2, 1993, pages 281
CHEMISTRY-A EUROPEAN JOURNAL, vol. 4, no. 6, 1998, pages 1043
JOURNAL OF FLUORINE CHEMISTRY, vol. 118, no. 1-2, 2002, pages 123
T. BENNECHE ET AL., SYNTHESIS, 1983, pages 762
M. MATTEUCCI, TETRAHEDRON LETTERS, vol. 31, 1990, pages 2385
ALUL ET AL., NUCLEIC ACIDS RESEARCH, vol. 19, 1991, pages 1527
WRIGHT ET AL., TETRAHEDRON LETTERS, vol. 34, 1993, pages 3373
GREENE T.W. ET AL.: "PROTECTIVE GROUPS IN ORGANIC SYNTHESIS", vol. 3RD ED., 1999, JOHN WILEY & SONS, INC., pages: 237 - 241, XP003017304
SANEYOSHI H. ET AL.: "A General Method for the Synthesis of 2'-O-Cyanoethylated Oligoribonucleotides Having Promising Hybridization Affinity for DNA and RNA and Enhanced Nuclease Resistance", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 70, no. 25, 2005, pages 10453 - 10460, XP003017305
DATABASE CAPLUS [online] OHGI T. ET AL.: "A New RNA Synthetic Method with a 2'-O-(2-Cyanoethoxymethyl) Protecting Group", XP003017306, accession no. STN Database accession no. (2005:582219)
WU X. ET AL.: "Synthesis of 5'-C- and 2'-O-(Bromoalkyl)-Substituted Ribonucleotide Phosphoramidites of the Post-synthetic Functionalization of Oligonucleotides on Solid Support", HELVETICA CHIMICA ACTA, vol. 83, no. 6, 2000, pages 1127 - 1144, XP003009347
ITO T. ET AL.: "(Methoxyethoxy)methyl Group: New Amide and Hydroxyl Protecting Group of Uridine in Oligonucleotide Synthesis", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 51, no. 6, 1986, pages 931 - 933, XP002979646
OHGI ET AL., ORGANIC LETTERS, vol. 7, 2005, pages 3477
TAKESHI WADA, BIO INDUSTRY, vol. 21, no. 1, 2004, pages 17
UMEMOTO ET AL., TETRAHEDRON LETTERS, vol. 45, 2004, pages 9529
HISAO SANEYOSHI ET AL., JOURNAL OF ORGANIC CHEMISTRY, vol. 70, 2005, pages 10453
JOURNAL OF MOLECULAR STRUCTURE, vol. 193, 1989, pages 247
POLISH JOURNAL OF CHEMISTRY, vol. 67, no. 2, 1993, pages 281
CHEMISTRY-A EUROPEAN JOURNAL, vol. 4, no. 6, 1998, pages 1043
JOURNAL OF FLUORINE CHEMISTRY, vol. 118, no. 1-2, 2002, pages 123
T. BENNECHE ET AL., SYNTHESIS, 1983, pages 762
M. MATTEUCCI, TETRAHEDRON LETTERS, vol. 31, 1990, pages 2385
ALUL ET AL., NUCLEIC ACIDS RESEARCH, vol. 19, 1991, pages 1527
WRIGHT ET AL., TETRAHEDRON LETTERS, vol. 34, 1993, pages 3373
Attorney, Agent or Firm:
SHIMIZU, Naoto (NIPPON SHINYAKU CO. LTD., 14, Kisshoin Nishinosho Monguchicho, Minami-ku, Kyoto-sh, Kyoto 50, JP)
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