93130-36-0Relevant academic research and scientific papers
2-(4-Nitrophenyl)ethyl Methylenebis(phosphonate): A Versatile Reagent for the Synthesis of Nucleoside 5′-Methylenebis(phosphonate)s
Lesiak, Krystyna,Watanabe, Kyoichi A.,George, Jay,Pankiewicz, Krzysztof W.
, p. 1906 - 1909 (2007/10/03)
2-(4-Nitrophenyl)ethyl methylenebis(phosphonate) (6) was prepared by reaction of equimolar amounts of 2-(4-nitrophenyl)ethyl alcohol and methylenebis(phosphonyl) tetrachloride in the presence of tetrazole. Compound 6 was further converted into the corresponding 4-nitrophenylethyl trisanhydride intermediate 7 by dehydration with diisopropylcarbodiimide (DIC). Reaction of 7 with either 2′,3′-O-isopropylideneadenosine (8a) or 2′,3′-O-isopropylideneguanosine (8b) afforded, after hydrolysis, the desired P 1-[2-(4-nitrophenyl)ethyl]-F2-(2′,3′-O- isopropylideneadenosin-5′-yl) methylenebis(phosphonate) (9a) and guanosine analogue 9b, respectively. A similar treatment of intermediate 7 with 3′-O-acetylthymidine (12a), 3′-O-acetyl-2′-deoxy-N4-benzoylcytidine (12b), 3′O-acetyl-2′-deoxy-N6-benzoyladenosine (12c), and 3′-O-acetyl-2′-deoxy-N2-isobutyrylguanosine (12d) gave the corresponding 2-(4-nitrophenyl)ethyl methylenebis(phosphonate)s 13a-d. These compounds as well as 9a,b were treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) which caused elimination of the 2-(4-nitrophenyl)ethyl group. The base labile 3′-O-acetyl, N4-acetyl, N6-benzoyl, and N2-isobutyryl groups of 12a-d were also removed during the DBU treatment. Thus, the 5′methylenebis(phosphonate)s of 2′,3′-O-isopropylideneadenosine (10a), 2′,3′-O-isopropylideneguanosine (10b), thymidine (14a), 2′-deoxycytidine (14b), 2′-deoxyadenosine (14c), and 2′deoxyguanosine (14d) were prepared in good yield. De-O-isopropylidenation of 10a and 10b afforded adenosine 5′-methylenebis(phosphonate) (11a) and guanosine 5′-methylenebis(phosphonate) (11b), respectively.
2-Vinylpyridine : A novel reagent for O6 protection of 2′-deoxyguanosine
Kumar, Prabhat,Singh,Misra
, p. 657 - 661 (2007/10/03)
2-Vinylpyridine has been successfully used for the protection of O6/N-1-lactam function in N2, 3′, 5′-protected 2′-deoxyguanosine followed by phosphonylation at 3′-end to yield the fully protected monomer for oligonucleotide synthesis, It is easier to introduce this group and then deprotect under milder conditions using 1, 8-diazabicyclo[5.4.0]undec-7-ene in anhyd. pyridine. Two oligonucleotides, viz. a hexamer, d(ACTGGC) and an octamer, d(GCCACTGT) have been synthesised in fairly good yields using this monomer on solid-phase without any side reactions.
(2-Pyridyl)methyl, a novel rwagent for O6 protection of 2'-deoxyguanosine
Awasthi, S. K.,Khanna, V.,Watal, G.,Misra, K.
, p. 916 - 919 (2007/10/02)
(2-Pyridyl)methyl group has been successfully used for the protection of O6 function in partially protected 2'-deoxyguanosine via 'Mitsunobu alkylation' to yield the fully protected monomer units for oligonucleotide synthesis.The group is easier to introduce and deprotect under milder conditions using 1,8-diazabicycloundec-7-ene (DBU) in anhyd. pyridine.A trimer d(GGA) and hexamer d(GGATCC) have been synthesized using this protected unit without any significant side reactions.
Improved Synthesis of Oligodeoxyribonucleotides by Solid-Phase Phosphotriester Method Utilizing O6--2'-deoxyguanosine Derivatives
Chollet, Andre,Ayala, Edgar,Kawashima, Eric H.
, p. 1356 - 1364 (2007/10/02)
The synthesis of oligodeoxyribonucleotides on a cross-linked polystyrene solid support utilizing stable mono- and dinucleotide phosphotriester building blocks is presented.The use of O6--2'deoxyguanosine derivatives yields cleaner DNA fragments by supressing side reactions.Modifications improving the phosphotriester methodology are presented.The purification methods and analysis of synthetic oligodeoxyribonucleotides are described.
