91702-60-2Relevant articles and documents
Engineering a selective small-molecule substrate binding site into a deoxyribozyme
Hoebartner, Claudia,Silverman, Scott K.
, p. 7420 - 7424 (2008/09/18)
A small goal: An RNA ligase deoxyribozyme is engineered to accept a small-molecule NTP substrate in a multiple-turnover fashion. Selective binding is enforced by hydrogen bonding, and structural preorganization within the NTP itself is important for its efficient utilization as a substrate. This study points the way toward a broader use of small-molecule substrates with nucleic acid enzymes. (Figure Presented)
Synthesis and comparative cytostatic activityof the new N-7 acyclic purine nucleoside analogues with natural N-9 regioisomers
Prekupec, Svjetlana,Kalokira, Blanka,Grdisa, Mira,Pavelic, Kresimir,De Clercq, Erik,Mintas, Mladen,Raid-Malic, Silvana
, p. 787 - 796 (2007/10/03)
The synthesis of the purine derivatives alkylated at N-7 (2a) and N-9 (2b) with 2-acetoxyethoxymethyl side chain, and chemical transformations of keto to chloro (5a), chloro to thio (6a) at C-6, and amino to fluoro (7a) at C-2 position of the purine ring were described. Structures of compounds were elucidated by analysis of their 1H and 13C NMR spectra, MS spectra and elemental analyses. N-7 Regioisomers (2a-7a) were evaluated for their cytostatic activities and their inhibitory effects were compared with those of the corresponding N-9 isomers. The 2-aminopurin-6-thione derivative (6a) showed the highest cytostatic activity, particularly against murine leukemia (L1210).
Regioselective synthesis of acyclovir and its various prodrugs
Gao,Mitra
, p. 1399 - 1419 (2007/10/03)
High-yield regioselective synthesis of 9-[(2-hydroxyethoxy)methyl]guanine (Acyclovir 1, Scheme 1) was achieved from guanine via trisilylated guanine. N2-acylacyclovir 9a-9b were prepared from N2, O-diacylacyclovir (4, 8b-8d) using regioselective deacylation procedure. N2-Acylacyclovir 11 and 13 were prepared via protection of primary hydroxyl groups. Three amino acid esters of acyclovir were synthesized as water-soluble prodrugs, which form protonated cations in pH 7.4 phosphate buffer. Two water-soluble ester prodrugs with free carboxylic acids, which form anionic species in pH 7.4 phosphate buffer, were also synthesized.
Structure and properties of 7,9-diglycosylguanine - An unstable intermediate in transglycosylation of guanine nucleosides
Boryski, Jerzy,Manikowski, Andrzej
, p. 1057 - 1059 (2007/10/03)
7,9-bis[(2-Acetoxyethoxy)methyl]-N2-acetylguanine (1), an unstable intermediate in the 7→9 transglycosylation of acyclovir, has been isolated and characterized by spectroscopy and chemical degradation.
Regioselectivity and mechanism of transpurination reactions in the guanine nucleosides series
Boryski, Jerzy
, p. 649 - 652 (2007/10/03)
The transpurination reaction of the fully acetylated derivatives of guanosine and its 7-β-D-ribofuranosyl regioisomer with 2-acetoxyethyl acetoxymethyl ether has been studied using high performance liquid chromatography (HPLC). The regioselectivity of glycosyl exchange observed in the early stages of the reaction suggests that the unsubstituted nitrogen atoms of the imidazole portion (N7 and N9) are, exclusively, sites of direct glycosylation in the case of guanine derivatives. The results lead to the conclusion that the mechanism of the glycosylation reaction of guanine is different to that of adenine.
Synthesis of 9-(2-hydroxyethoxymethyl)guanine (acyclovir) from guanosine
Shiragami,Koguchi,Tanaka,Takamatsu,Uchida,Ineyama,Izawa
, p. 337 - 340 (2007/10/02)
A convenient synthesis of 9-(2-hydroxyethoxymethyl)guanine (acyclovir) from guanosine by chemical transpurination was developed. The isomerization of the 7-isomer to the desired 9-isomer and the purification of the 9- isomer was achieved simply by concentration, heating and further crystallization.
