Open AccessSynthesis of Oligodeoxynucleotides Containing a C8‐2′‐Deoxyguanosine Adduct Formed by the Carcinogen 3‐Nitrobenzanthrone
Author(s) -
Chatterjee Arindom,
Malik Chanchal K.,
Basu Ashis K.
Publication year - 2017
Publication title -
current protocols in nucleic acid chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.306
H-Index - 17
eISSN - 1934-9289
pISSN - 1934-9270
DOI - 10.1002/cpnc.28
Subject(s) - deoxyguanosine , adduct , phosphoramidite , chemistry , oligonucleotide , carcinogen , nucleoside , dna , dna adduct , stereochemistry , combinatorial chemistry , biochemistry , organic chemistry
This unit describes the detailed procedure in five parts for the synthesis of the C8‐2′‐deoxyguanosine‐3‐aminobenzanthrone adduct located in a desired site in an oligonucleotide. The synthesis of the protected 2′‐deoxyguanosine, O 6 ‐benzyl‐ N 2 ‐DMTr‐3′‐5′‐bisTBDMS‐C8‐Br‐2′‐deoxyguanosine, is described in the first part. The synthesis of the reduced carcinogen 3‐aminobenzanthrone is detailed in part two. The third part outlines the key step of the adduct formation between the reduced carcinogen and the protected nucleoside by a palladium‐catalyzed cross coupling reaction. The final two parts describe phosphoramidite synthesis from the nucleoside‐carcinogen adduct followed by its site‐specific incorporation into DNA by solid‐phase oligonucleotide synthesis. The adducted oligonucleotides are purified by reversed‐phase HPLC and characterized by mass spectrometry. © 2017 by John Wiley & Sons, Inc.