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Synthesis 2010(21): 3710-3714
DOI: 10.1055/s-0030-1258243
DOI: 10.1055/s-0030-1258243
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Readily Accessible Triazole-Linked Dimer Deoxynucleoside Phosphoramidite for Solid-Phase Oligonucleotide Synthesis
Further Information
Received
25 June 2010
Publication Date:
07 September 2010 (online)
Publication History
Publication Date:
07 September 2010 (online)
Abstract
A concise preparation of triazole-linked deoxynucleoside phosphoramidite for its direct use in solid-phase oligonucleotide synthesis is reported. This dimer has successfully been utilized in solid-phase synthesis to make the 10- and 12-mer oligomers.
Key words
nucleotides - triazole - click - oligomer - solid-phase synthesis
-
1a
Koropatnick J.Berg RW.Jason TLH. Recent Development in Gene Therapy 1st ed.: Transworld Research Network; Trivandrum: 2007. p.151-180 -
1b
Haas J.Engels JW. Tetrahedron Lett. 2007, 48: 8891 -
1c
Buchini S.Leumann CJ. Curr. Opin. Chem. Biol. 2003, 7: 717 -
1d
Kurreck J. Eur. J. Biochem. 2003, 270: 1628 -
2a For
more recent papers on these derivatives see:
Olesiak M.Stec WJ.Okruszek A. Org. Biomol. Chem. 2009, 7: 2162 ; and references cited therein -
2b
Kanaori K.Tamura Y.Wada T.Nishi M.Kanehara H.Morii T.Tajima K.Makino K. Biochemistry 1999, 38: 16058 -
2c
De Mesmaeker A.Altmann KH.Waldner A.Wendeborn S. Curr. Opin. Struct. Biol. 1995, 5: 343 -
2d
Uhlmann E.Peyman A. Chem. Rev. 1990, 90: 543 -
2e
Brill WK.-D.Nielsen J.Carruthers MH. Tetrahedron Lett. 1988, 29: 5517 -
3a
Li P.Sergueeva ZA.Dobrikov M.Shaw BR. Chem. Rev. 2007, 107: 4746 -
3b
Higashida R.Oka N.Kawanaka T.Wada T. Chem. Commun. 2009, 2466 -
3c For other derivatives
including boronates, see:
Han Q.Sarafianos SG.Arnold E.Parniak MA.Gaffney BL.Jones RA. Tetrahedron 2009, 65: 7915 -
4a
Nina M.Fonne-Pfister R.Beaudegnies R.Chekatt H.Jung PMJ.Murphy-Kessabi F.de Mesmaeker A.Wendeborn S. J. Am. Chem. Soc. 2005, 127: 6027 -
4b
de Mesmaeker A.Lebreton J.Waldner A.Fritsch V.Wolf RM. Bioorg. Med. Chem. Lett. 1994, 4: 873 -
5a
Viswanadham G.Petersen GV.Wengel J. Bioorg. Med. Chem. Lett. 1996, 6: 987 -
5b
Petersen GV.Wengel J. Tetrahedron 1995, 51: 2145 -
6a
Matt PV.Lochmann T.Altmann K.-H. Bioorg. Med. Chem. Lett. 1997, 7: 1549 -
6b
Matt PV.Altmann K.-H. Bioorg. Med. Chem. Lett. 1997, 7: 1553 -
6c
Filichev VV.Malin AA.Ostrovskii VA.Pedersen EB. Helv. Chim. Acta 2002, 85: 2847 - 7
Isobe H.Fujino T.Yamazaki N.Guillot-Nieckowski M.Nakamura E. Org. Lett. 2008, 10: 3729 - For few recent publications, see:
-
8a
Koissi N.Lonnberg H. Nucleosides, Nucleotides, Nucleic Acids 2007, 26: 1203 -
8b
Krueger AT.Lu H.Lee AHF.Kool ET. Acc. Chem. Res. 2007, 40: 141 -
8c
Liu H.Gao J.Kool ET. J. Am. Chem. Soc. 2005, 127: 1396 -
8d
Kool ET. Acc. Chem. Res. 2002, 35: 936 - For few recent sugar modified nucleosides, see:
-
9a
Stauffiger A.Leumann CJ. Eur. J. Org. Chem. 2009, 1153 -
9b
Prakash TP.Bhat B. Curr. Top. Med. Chem. 2007, 7: 641 -
9c
Gagneron J.Gosselin G.Mathe C. Eur. J. Org. Chem. 2006, 4891 -
9d
Prakash TP.Kawasaki AM.Lesnik EA.Owens SR.Manoharan M. Org. Lett. 2003, 5: 403 -
10a
Nielsen PE. Pure Appl. Chem. 1998, 70: 105 -
10b
Fujii M.Yoshida K.Hidaka J.Ohtsu T. Bioorg. Med. Chem. Lett. 1997, 7: 637 -
11a
Zhang N.Tan C.Cai P.Zhang P.Zhao Y.Jiang Y. Bioorg. Med. Chem. 2009, 17: 2441 -
11b
Summerton J.Weller D. Nucleosides Nucleotides 1997, 16: 889 - 12 For a recent review, see:
Amblard F.Cho JH.Schinazi RF. Chem. Rev. 2009, 109: 4207 ; and references cited therein - 13
Chandrasekhar S.Basu D.Rambabu Ch. Tetrahedron Lett. 2006, 47: 3059 - 14
Srihari P.Dutta P.Srinivasa Rao R.Yadav JS.Chandrasekhar S.Thombare P.Mohapatra J.Chatterjee A.Jain MR. Bioorg. Med. Chem. 2009, 19: 5569 - For other contributions on click chemistry from our group, see:
-
15a
Chandrasekhar S.Lohitha Rao Ch.Nagesh Ch.Raji Reddy Ch.Sridhar B. Tetrahedron Lett. 2007, 48: 5869 -
15b
Chandrasekhar S.Tiwari B.Parida BB.Raji Reddy Ch. Tetrahedron: Asymmetry 2008, 19: 495 -
15c
Chandrasekhar S.Seenaiah M.Lohitha Rao Ch.Raji Reddy Ch. Tetrahedron 2008, 64: 11325 -
16a
Lazrek HB.Rochdi A.Engels JW. Nucleosides Nucleotides 1999, 18: 1257 - For recent papers with triazoles, see:
-
16b
Nuzzi A.Massi A.Dondoni A. QSAR Comb. Sci. 2007, 26: 1191 -
16c
Lucas R.Neto V.Hadj Bouazza A.Zerrouki R.Granet R.Krausz Champavier Y. Tetrahedron Lett. 2008, 49: 1004 -
16d
Lucas R.Zerrouki R.Granet R.Champavier YK. Tetrahedron 2008, 64: 5467 -
16e
Isobe H.Fujino T.Yamazaki N. Tetrahedron Lett. 2009, 50: 4101 ; and references cited therein -
16f
El-Sagheer AH.Brown T. J. Am. Chem. Soc. 2009, 131: 3958 - 17
Chandrasekhar S.Rambabu Ch.Syamprasad Reddy A. Org. Lett. 2008, 10: 4355 -
18a
Corey EJ.Fuchs PL. Tetrahedron Lett. 1972, 13: 3769 -
18b
Takahashi S.Nakata T. J. Org. Chem. 2002, 67: 5739
References
Initially, the reaction was tried with n-BuLi and the yield was found to be poor as the reaction ended with an intractable mixture of products.