85394-19-0Relevant articles and documents
Self-sacrificing acetylation observed during attempted desilylation of 1-[4-benzenesulfonyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-5-O-methanesulfonyl- α-l-threo-pentofuranosyl]thymine
Shimada, Hisashi,Kubota, Yutaka,Tanaka, Hiromichi
body text, p. 4253 - 4255 (2010/09/07)
Desilylation of 1-[4-benzenesulfonyl-3-O-(tert-butyldimethylsilyl)-2-deoxy- 5-O-methanesulfonyl-α-l-threo-pentofuranosyl]thymine (4) with Bu 4NF/THF, when carried out at room temperature, gave four products. Among these, there were 1-[3-O-acetyl-4-benzenesulfonyl-2-deoxy-5-O- methanesulfonyl-α-l-threo-pentofuranosyl]thymine (7) and thymine. A possible reaction mechanism is proposed, which suggests the origin of 3′-O-acetyl group of 7 and thymine as well as structures of the other two products (9a and 9b).
Cleavage of single-stranded 4′-oligonucleotide radicals in the presence of O2
Giese, Bernd,Beyrich-Graf, Xenia,Erdmann, Peter,Giraud, Luc,Imwinkelried, Petra,Müller, Stephan N.,Schwitter, Urs
, p. 6146 - 6147 (2007/10/02)
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Chemistry of 4'-Hydroperoxy Nucleosides as a Model for the Intermediate in Bleomycin-Induced Degradation of DNA
Saito, Isao,Morii, Takashi,Matsuura, Teruo
, p. 1008 - 1012 (2007/10/02)
The reaction of 1-(3-O-benzoyl-2,5-dideoxy-β-D-glycero-pent-4-enofuranosyl)thymine (5) with anhydrous hydrogen peroxide in the presence of trifluoroacetic acid gave two isomeric 4'-hydroperoxides (6 and 7).The structure of the major product was assigned as 3'-O-benzoyl-5'-deoxy-4'-hydroperoxythymine (6) on the basis of spectral data.It has been demonstrated that the 4'-hydroperoxide 6 is capable of undergoing a Criegee-type rearrangement in an aqueous buffered solution to give trans-3-(thymin-1'-yl)propenal (10) stereospecifically, whereas the more stable isomer 7 does not produce 10 under the same conditions.These model experiments suggest that once a 4'-hydroperoxy intermediate of β-D-deoxyribo configuration is formed by action of the activated bleomycin on DNA, it spontaneously decomposes to afford DNA strand scission and trans base propenal.Reduction of these 4'-hydroperoxy nucleosides with dimethyl sulfide in methanol gave thymine and γ-keto aldehyde 14 quantitatively.The result indicates that the 4'-hydroxy nucleoside might be the precursor of alkali-labile lesion in DNA.