236427-57-9Relevant academic research and scientific papers
Synthesis and reactions of 2-chloro- and 2-tosyloxy-2′-deoxyinosine derivatives
Pottabathini, Narender,Bae, Suyeal,Pradhan, Padmanava,Hahn, Hoh-Gyu,Mah, Heduck,Lakshman, Mahesh K.
, p. 7188 - 7195 (2007/10/03)
Convenient syntheses of 2-chloro- and 2-tosyloxy-2′-deoxyinosine as their tert-butyldimethylsilyl ethers are described. Both compounds can be synthesized via a common route and rely on commercially available 2′-deoxyguanosine. The present method leading t
Chemical synthesis of cross-link lesions found in nitrous acid treated DNA: A general method for the preparation of N2-substituted 2'- deoxyguanosines
Harwood, Eric A.,Hopkins, Paul B.,Sigurdsson, Snorri Th.
, p. 2959 - 2964 (2007/10/03)
Treatment of DNA with nitrous acid results in the formation of DNA-DNA cross-links. Two cross-link lesions have previously been isolated and their structures assigned based on spectroscopic data. The major lesion has been proposed to consist of two deoxyguanosine (dG) nucleosides sharing a common N2 atom (1), while the structure of the minor lesion has been proposed to consist of a common nitrogen atom linking C2 of a dG nucleoside to C6 of deoxyadenosine (2). The chemical synthesis of 1 and 2, utilizing a palladium- catalyzed coupling, is described herein. It is demonstrated that the spectroscopic properties of synthetic 1 are identical to that of lesion 1 obtained from nitrous acid cross-linked DNA, thus providing a proof of its structure. Comparison of the limited spectroscopic data available for lesion 2 originating from nitrous acid cross-linked DNA to synthetic 2 supports its structural assignment. The synthetic approach used for synthesis of 1 and 2 is shown to be a general method for the preparation of a variety of N2- substituted dG nucleosides in good yields.
Facile synthesis of O6-alkyl-, O6-aryl-, and diaminopurine nucleosides from 2′-deoxyguanosine
Lakshman, Mahesh K.,Ngassa, Felix N.,Keeler, John C.,Dinh, Yen Q. V.,Hilmer, John H.,Russon, Larry M.
, p. 927 - 930 (2007/10/03)
(equation presented) The 3′,5′-bis-O-TBDMS derivative of 2′-deoxyguanosine can be converted to its O6-alkyl and O6-aryl ethers as well as to N6-substituted diaminopurine nucleosides in two simple steps. Also described is a
