Nucleosides. LXV. Synthesis of New Pteridine-N8-Nucleosides

Nucleosides, Nucleotides and Nucleic Acids

Volumn 23, Issue 1-2, 2004, Pages 51-66

  Matysiak, Stefan ^a   Waldscheck, Bernhard ^a   Pfleiderer, Wolfgang ^a  

^a UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

2 (4 nitrophenyl)ethyl protecting group; Mitsunobu reaction; Pteridine nucleosides; Ribosylation reactions

Indexed keywords

ACETIC ACID DERIVATIVE; ALCOHOL DERIVATIVE; AMIDE; AMINE; CARBOHYDRATE DERIVATIVE; DEOXYRIBONUCLEOSIDE; ISOXANTHOPTERIN; MESYLIC ACID DERIVATIVE; NUCLEOSIDE DERIVATIVE; PALLADIUM; PTERIDINE DERIVATIVE; RIBOSE;

ARTICLE; BENZYLATION; CATALYSIS; ELIMINATION REACTION; HALOGENATION; MITSUNOBU REACTION; OXIDATION; REACTION ANALYSIS; SYNTHESIS;

NUCLEOSIDES; PTERIDINES;

EID: 1542785034     PISSN: 15257770     EISSN: None     Source Type: Journal    
DOI: 10.1081/NCN-120027817     Document Type: Article

References (17)

1. Münch, U.; Pfleiderer, W. Nucleosides LXIV. Base-labile protecting groups for oligoribonucleotide synthesis. Helv. Chim. Acta 2002, 85, 1504-1517.
2. Schmid, H.; Schranner, M.; Pfleiderer, W. Nucleoside XI. Synthese von Isoxanthopterin-N-8-β-D-ribofuranosid-ein strukturanaloges Nucleosid des Guanosins. Chem. Ber. 1973, 106, 1952-1975.
3. Ritzmann, G.; Ienaga, K.; Pfleiderer, W. Nucleoside XXIV. Verbesserte Synthesen von Lumazinnucleosiden. Liebigs Ann. Chem. 1977, 1217-1234.
4. Harris, R.; Pfleiderer, W. Nucleoside XXXVI. Synthese und Eigenschaften des 4-amino-8-β-D-ribofuranosyl-7(8H)-pteridones sowie seiner 2- und 6-Phenylderivate. Liebigs Ann. Chem. 1981, 1457-1468.
5. Hawkins, M.E.; Pfleiderer, W.; Mazumder, A.; Pommier, Y.G.; Balis, F.M. Incorporation of a fluorescent guanosine analog into oligonucleotides and its application to a real time assay for the HIV-1 integrase 3′-processing reaction. Nucleic Acids Res. 1995, 23, 2872-2880.
6. Jungmann, O.; Pfleiderer, W. A new efficient method in nucleoside synthesis. Tetrahedron Lett. 1996, 37, 8355-8358.
7. Melguizo, M.; Gottlieb, M.; Charubala, R.; Pfleiderer, W. Nucleosides LXII. Synthesis of 6-methyl-8-(2-deoxy-β-D-ribofuranosyl)-isoxanthopterin and derivatives. Nucleosides Nucleotides 1998, 17, 175-186.
8. 8-(2′ -deoxy-β-D-ribonucleosides): new fluorescence markers for oligonucleotide synthesis. Helv. Chim. Acta 2001, 84, 2330-2342.
9. Hawkins, M.E.; Pfleiderer, W.; Balis, F.M.; Porter, D.; Knutson, J.R. Fluorescence properties of pteridine nucleoside analogs as monomers and incorporated into oligonucleotides. Anal. Biochem. 1997, 244, 86-95.
10. Bannwarth, W.; Müller, F. Energy transfer from a lumazine (= Pteridine-2, 4-(1H, 3H)dione) chromophore to bathophenanthroline-ruthenium (II) complexes during hybridization processes of DNA. Helv. Chim. Acta 1991, 74, 2000-2008.
11. Bannwarth, W.; Pfleiderer, W.; Müller, F. Energy transfer within oligonucleotides from a lumazine chromophore to bathophenanthroline-ruthenium(II) complexes. Helv. Chim. Acta 1991, 74, 1991-1999.
12. Driscoll, S.; Hawkins, M.E.; Balis, F.M.; Pfleiderer, W.; Laws, W.R. Fluorescence properties of a new guanosine analog incorporated into small oligonucleotides. Biophys. J. 1997, 73, 3277-3286.
13. Birkofer, L.; Ritter, A.; Kühlthau, H.P. Alkylierungen und Glykosidierungen über Silyl-Derivative. Chem. Ber. 1964, 97, 934-945.
14. Birkofer, L.; Ritter, A. Die Silylierung als Hilfsmittel in der Organischen Synthese. Angew. Chem. 1965, 77, 414-426.
15. Kiriasis, L.; Pfleiderer Nucleoside XLV. Synthese von 8-β-D-ribofuranosyl-leukopterin. Nucleosides Nucleotides 1989, 8, 1345-1358.
16. Ritzmann, G.; Ienaga, K.; Kiriasis, L.; Pfleiderer, W. Nucleoside XXXIII. Über die Synthese des 7-Oxo-8-β-D-ribofuranosyl-7,8-dihydrolumazins und seines 6-Methyl-derivates. Chem. Ber. 1980, 113, 1535-1548.
17. Johns, C.O.; Baumann, E.J. Researches in purines. On 2-methylmercapto-6,8-dioxypurine and 2-methylmercapto-6-oxy-8-aminopurine. J. Biol. Chem. 1913, 14, 381-388.