Hydrolysis of nucleosides related to wyosine

Itaya, Taisuke; Harada, Taku

doi:10.1039/c39840000858

Cited by 14 publications

(10 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…By employing milder conditions (K 2 CO 3 instead of NaH, and addition of KI) this problem was avoided, but now an efficient N(4)-alkylation of the product 4 was In preliminary studies with unprotected wyosine, its compatibility with RNA assembly and deprotection conditions was investigated. In addition to the instability of wyosine towards acid [10] and towards MeNH 2 5 ), the nucleoside was found to be efficiently iodinated under the standard oxidation conditions (I 2 /H 2 O/pyridine in THF [11]) 6 ). Oxidation with t BuOOH in MeCN according to [14], and a milder deprotection which involved treatment of the solid support with i Pr 2 NH in MeCN, followed by NH 3 in MeOH, however, were fully compatible with wyosine.…”

Section: Results Andmentioning

confidence: 99%

“…Due to its lability towards acid (t 1/2 ¼ 95 s at pH 1 and 258) [10], wyosine itself is not fully compatible with the automated assembly of RNA sequences 3 ) and can only be incorporated as the last nucleotide at the 5'-end. Therefore, its presence at an interior position within a RNA sequence requires the enzymatic ligation of the 5'-wyosine ending sequence with another strand (Scheme 1).…”

mentioning

confidence: 99%

“…b) Plot of the amount of the ligated products(1,10,18,20,22) relative to the sum of starting material 8mer 12 and 10mers of the respective(11,16,17,19, 21) RNA sequences.…”

mentioning

confidence: 99%

“…) HÀN(4) in desmethylwyosine has a pK a value of 3.24[13].5 ) The attempted deacetylation of 8 with MeNH 2 in EtOH resulted in ring-opening, presumably by attack on C(9)[10] 6. ) Iodination is known to occur in a selective and efficient manner at position 7 and has been applied for the preparation of wybutosine[7].…”

mentioning

confidence: 99%

See 3 more Smart Citations

Chemical Approach for the Study of the ‘Kissing Complex’ of Moloney murine leukaemia Virus

Porcher

2008

Helvetica Chimica Acta

View full text Add to dashboard Cite

The replication of Moloney murine leukaemia virus relies on the formation of a stable homodimeric kissing complex of a GACG tetraloop interacting through only two C · G base pairs flanked of 5'adjacent unpaired adenosines A9. Previous NMR investigations of a model stem loop 1 has not permitted to reveal the origin of this interaction. Therefore, with the aim of deeper comprehension of the phenomena, the model sequence 10 was prepared where position 9 has been substituted for a nucleoside offering a wider p-stacking. In this context, the wyosine phosphoramidite building block 2 was prepared and incorporated by adapting the conditions of the automated synthesis and developing original templated enzymatic ligation. However, no kissing interaction has been observed for this model sequence 10 due to steric hindrance as confirmed by computational simulation. Consequently, several other model sequences, 18, 23 -26, containing modified nucleosides were prepared. Finally, the importance of the cross-loop H-bond between G8 and G11 nucleobases was revealed by preparing a 18mer RNA hairpin 27, where the guanosine G8 has been substituted for inosine. The latter, which does not possess a C 3 amino function compared to guanosine, is unable to form any kissing complex demonstrating the importance of this secondary interaction in the formation of the complex.

show abstract

Section: Results Andmentioning

confidence: 99%

mentioning

confidence: 99%

“…b) Plot of the amount of the ligated products(1,10,18,20,22) relative to the sum of starting material 8mer 12 and 10mers of the respective(11,16,17,19, 21) RNA sequences.…”

mentioning

confidence: 99%

mentioning

confidence: 99%

See 2 more Smart Citations

Chemical Approach for the Study of the ‘Kissing Complex’ of Moloney murine leukaemia Virus

Porcher

2008

Helvetica Chimica Acta

View full text Add to dashboard Cite

show abstract

“…This could be explained by the high lability of the N-glycosidic bond of dAdo-N3 adduct [25], and, consequently, the initially formed glycosylated adduct undergoes depurination faster than the further reactions with nucleobases.…”

mentioning

confidence: 95%

Reactions of 4‐[Bis(2‐chloroethyl)amino]benzenebutanoic Acid (Chlorambucil) with DNA

Florea-Wang

Pawłowicz

Sinkkonen

et al. 2009

Chemistry & Biodiversity

View full text Add to dashboard Cite

4-[Bis(2-chloroethyl)amino]benzenebutanoic acid (=chlorambucil, 1; 2.5 mM) was allowed to react with single- and double-stranded calf thymus DNA at physiological pH (cacodylic acid, 50% base) at 37 degrees . The DNA-chlorambucil adducts were identified by analyzing the DNA hydrolysates by NMR, UV, HPLC, LC/ESI-MS/MS techniques as well as by spiking with authentic materials. ssDNA was more reactive than dsDNA, and the order of reactivity in ssDNA was Ade-N1>Gua-N7>Cyt-N3>Ade-N3. The most reactive site in dsDNA was Ade-N3. The Gua-N7 and Ade-N3 adducts were hydrolytically labile. Ade-N7 adduct could not be identified in the hydrolysates of ssDNA or dsDNA. The adduct Gua-N7,N7, which consists of two units of Gua bound together with a unit derived from chlorambucil, is a cross-linking adduct, and it was detected in the hydrolysates of ssDNA and dsDNA. Also several other adducts were detected which could be characterized by spiking with previously isolated authentic adducts or tentatively by MS. The role of chlorambucil-DNA adducts on the cytotoxicity and mutagenity of 1 is also discussed.

show abstract

Protecting Groups in Oligonucleotide Synthesis

Sonveaux

1994

Protocols for Oligonucleotide Conjugates

View full text Add to dashboard Cite

Hydrolysis of nucleosides related to wyosine

Cited by 14 publications

References 0 publications

Chemical Approach for the Study of the ‘Kissing Complex’ of Moloney murine leukaemia Virus

Chemical Approach for the Study of the ‘Kissing Complex’ of Moloney murine leukaemia Virus

Reactions of 4‐[Bis(2‐chloroethyl)amino]benzenebutanoic Acid (Chlorambucil) with DNA

Protecting Groups in Oligonucleotide Synthesis

Contact Info

Product

Resources

About