[Synthesis of nucleotide derivatives containing 1-(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzamido)-2,3-propanediol for photoaffinity modification of proteins and nucleic acid].
1-(4-(3-(Trifluoromethyl)-3H-diazirin-3-yl)benzamido)-3-O-(4,4'- dimethoxytrityl)-2,3-propanediol phosphoramidite was synthesized and used as a modified unit in the automatic synthesis of oligodeoxyribonucleotides. Pentadecathymidylates with various numbers of 2,3-propanediol moieties substituted with aryl(trifluoromethyl)diazirinyl (ATFMD) were obtained, and the thermal stability of their duplexes with (dA)15 were studied. One ATFMD-propanediol residue was shown to reduce the thermal stability of the duplex by 8-9 degrees C. The irradiation of the ATFMD-containing duplexes by UV light with the wavelength of 350 nm was found to cause the cross-linking reaction of the ATFMD-containing strand with the complementary strand and the formation of the cross-linked duplexes. The photomodification efficiency was independent of the oligonucleotide sequence, with each ATFMD group providing for 5% cross-linking. The irradiation of an ATFMD-containing duplex, a substrate of the HIV-1 integrase, in the presence of this enzyme resulted in the covalent DNA-protein complex. The oligonucleotides with the 1-(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzamido)-2,3-propanediol moiety in their chains can be used for the photoaffinity modification of both nucleic acids and proteins that recognize them. The English version of the paper: Russian Journal of Bioorganic Chemistry, 2002, vol. 28, no. 4; see also http://www.maik.ru.
Agapkina
Iu Iu
IuIu
Institute of Chemical Physics Problems, Russian Academy of Sciences, Institutskii pr. 14, Chernogolovka, Moscow Oblast, 142432 Russia. jagapkina@rambler.ru
Agapkin
D V
DV
Zagorodnikov
A V
AV
Alekseev
Ia I
IaI
Korshunova
G A
GA
Gottikh
M B
MB
D001389:Azirines / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects; D003432:Cross-Linking Reagents / Q000737:chemistry; D018076:DNA, Complementary / Q000737:chemistry; D004279:DNA, Viral / Q000737:chemistry; D004591:Electrophoresis, Polyacrylamide Gel; D019427:HIV Integrase / Q000737:chemistry / Q000528:radiation effects; D015497:HIV-1; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects; D009841:Oligonucleotides / Q000737:chemistry; D019920:Photoaffinity Labels / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects; D011409:Propylene Glycols / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects; D014466:Ultraviolet Rays
C465423:1-(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzamido)-3-O-(4,4'- dimethoxytrityl)-2,3-propanediol phosphoramidite; D001389:Azirines; D003432:Cross-Linking Reagents; D018076:DNA, Complementary; D004279:DNA, Viral; D009838:Oligodeoxyribonucleotides; D009841:Oligonucleotides; D019920:Photoaffinity Labels; D011409:Propylene Glycols; C406744:pentadecathymidylic acid; D019427:HIV Integrase