- Synthesis of pyrrolo[2,3-d]pyrimidines that are structurally related to methylated guanosines from tRNA and the nucleoside Q analogs, PreQ0 and PreQ1
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The N-3- and N-2-methylated analogs of several 5-substituted 2-amino-7- (β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidin-4-ones were synthesized from 5- cyano-2,4-dichloro-7-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrrolo[2,3- d]pyrimidine (10). These compounds are analogs of nucleoside Q that are methylated in a manner similar to some of the naturally occurring methylated guanosines.
- Cheng,Hoops,Earl,Townsend
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- PYRROLOPYRIMIDINE NUCLEOSIDES 19. A TOTAL SYNTHESIS OF THE NUCLEOSIDE ANTIBIOTIC CADEGUOMYCIN PYRIMIDIN-4-ONE-5-CARBOXYLIC ACID>
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A total synthesis of 2-amino-7-(β-D-ribofuranosyl)pyrrolopyrimidin-4-one-5-carboxylic acid has been accomplished and confirms the previous structural assignment for the nucleoside antibiotic cadeguomycin.
- Beylin, Vladimir G.,Kawasaki, Andrew M.,Cheng, Chin Shu,Townsend, Leroy B.
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Read Online
- A practical synthesis of archaeosine and its base
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A practical synthetic route to 7-formamidino-7-deazaguanosine (archaeosine), a hypermodified nucleoside observed in archaeal tRNA, has been developed, which involves the addition of hydroxylamine to the cyano group of 7-cyano-7-deazaguanosine (preQ0
- Oka, Natsuhisa,Fukuta, Akane,Ando, Kaori
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p. 5709 - 5714
(2018/08/21)
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- Efficient synthesis of deazaguanosine-derived tRNA nucleosides PreQ 0, PreQ1, and archaeosine using the Turbo-Grignard method
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The natural products PreQ1, PreQ0, and archaeosine are deazaguanosine-derived natural products of immense biological importance. All three are critical components of tRNAs and, as such, are involved in decoding genetic information. W
- Brueckl, Tobias,Thoma, Ines,Wagner, Andreas J.,Knochel, Paul,Carell, Thomas
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supporting information; experimental part
p. 6517 - 6519
(2011/02/22)
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- A short and efficient synthesis of the tRNA nucleosides PreQ0 and archaeosine
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Modified nucleosides in tRNAs play an important role in the translational process. They fine tune the codon-anticodon interactions and they influence the folding and stabilisation of the tRNA structure. Herein, we present a novel synthetic route to the highly modified nucleosides PreQ0 and archaeosine. The synthesis involves coupling of a protected 7-cyano-7- deazaguanosine nucleobase with a TBDMS and isopropylidene protected chloro-ribose unit yielding the PreQ0 nucleoside after deprotection. This PreQ0 nucleoside is then used as the starting material for the synthesis of archaeosine providing the first total synthetic access to this hypermodified RNA nucleoside. The Royal Society of Chemistry 2007.
- Brueckl, Tobias,Klepper, Florian,Gutsmiedl, Katrin,Carell, Thomas
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p. 3821 - 3825
(2008/10/09)
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- Nucleoside derivatives as inhibitors of RNA-dependent RNA viral polymerase
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The present invention provides nucleoside compounds and certain derivatives thereof which are inhibitors of RNA-dependent RNA viral polymerase. These compounds are inhibitors of RNA-dependent RNA viral replication and are useful for the treatment of RNA-dependent RNA viral infection. They are particularly useful as inhibitors of hepatitis C virus (HCV) NS5B polymerase, as inhibitors of HCV replication, and/or for the treatment of hepatitis C infection. The invention also describes pharmaceutical compositions containing such nucleoside compounds alone or in combination with other agents active against RNA-dependent RNA viral infection, in particular HCV infection. Also disclosed are methods of inhibiting RNA-dependent RNA polymerase, inhibiting RNA-dependent RNA viral replication, and/or treating RNA-dependent RNA viral infection with the nucleoside compounds of the present invention.
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- SYNTHESES OF HYPERMODIFIED NUCLEOSIDE Q, AND ITS BIOSYNTHETIC PRECURSORS PREQ0 AND PREQ1
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The nucleoside Q (1) and its biosynthetic precursors, preQ0 (2) and preQ1 (3) were synthesized from the key intermediate, 6-bromo-2-diacetylamino-3,4-dihydro-3-methoxymethyl-5-methyl-7-(5-O-acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-7H-pyrrolopyrimidin-4-one (6) by conversion of the methyl group on the base to 3S,4R,5S-4,5-dihydroxycyclopent-1-en-3-ylaminomethyl, cyano, and aminomethyl groups, respectively.
- Kondo, Tadao,Okamoto, Kaoru,Ohgi, Tadaaki,Goto, Toshio
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p. 207 - 213
(2007/10/02)
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