scholarly journals 8-Fluoro-N-2-isobutyryl-2′-deoxyguanosine: Synthesis and Reactivity

Molbank ◽  
10.3390/m1119 ◽  
2020 ◽  
Vol 2020 (1) ◽  
pp. M1119 ◽  
Author(s):  
Andrei Solodinin ◽  
James Helmkay ◽  
Samuel Ollivier ◽  
Hongbin Yan

3′,5′-O-Bis(tert-butyldimethylsilyl)-8-fluoro-N-2-isobutyryl-2′-deoxyguanosine was synthesized from 3′,5′-O-bis(tert-butyldimethylsilyl)-N-2-isobutyryl-2′-deoxyguanosine by the treatment with N-fluorobenzenesulfonimide. A similar fluorination reaction with 3′,5′-O-bis(tert-butyldimethylsilyl)-N-2-(N,N-dimethylformamidine)-2′-deoxyguanosine, however, failed to give the corresponding fluorinated product. It was found that 8-fluoro-N-2-isobutyryl-2′-deoxyguanosine is labile under acidic conditions, but sufficiently stable in dichloroacetic acid used in solid phase synthesis. Incorporation of 8-fluoro-N-2-isobutyryl-2′-deoxyguanosine into oligonucleotides through the phosphoramidite chemistry-based solid phase synthesis failed to give the desired products. Furthermore, treatment of 8-fluoro-N-2-isobutyryl-2′-deoxyguanosine with aqueous ammonium hydroxide did not give 8-fluoro-2′-deoxyguanosine, but led to the formation of a mixture consisting of 8-amino-N-2-isobutyryl-2′-deoxyguanosine and C8:5′-O-cyclo-2′-deoxyguanosine. Taken together, an alternative N-protecting group and possibly modified solid phase synthetic cycle conditions will be required for the incorporation of 8-fluoro-2′-deoxyguanosine into oligonucleotides through the phosphoramidite chemistry-based solid phase synthesis.

2001 ◽  
Vol 42 (27) ◽  
pp. 4471-4474 ◽  
Author(s):  
Dolors Fernández-Forner ◽  
Gaspar Casals ◽  
Eloı́sa Navarro ◽  
Hamish Ryder ◽  
Fernando Albericio

1994 ◽  
Vol 336 (3) ◽  
pp. 233-236 ◽  
Author(s):  
G�nter Losse ◽  
Wolfgang Naumann ◽  
Andrea Winkler ◽  
Gabriele S�ptitz

2006 ◽  
Vol 10 (2) ◽  
pp. 251-256 ◽  
Author(s):  
Zacharia S. Cheruvallath ◽  
Alessandra Eleuteri ◽  
Brett Turney ◽  
Vasulinga T. Ravikumar

2019 ◽  
Vol 15 ◽  
pp. 1116-1128 ◽  
Author(s):  
Shahien Shahsavari ◽  
Dhananjani N A M Eriyagama ◽  
Bhaskar Halami ◽  
Vagarshak Begoyan ◽  
Marina Tanasova ◽  
...  

Solid-phase synthesis of electrophilic oligodeoxynucleotides (ODNs) was achieved using dimethyl-Dmoc (dM-Dmoc) as amino protecting group. Due to the high steric hindrance of the 2-(propan-2-ylidene)-1,3-dithiane side product from deprotection, the use of excess nucleophilic scavengers such as aniline to prevent Michael addition of the side product to the deprotected ODN during ODN cleavage and deprotection was no longer needed. The improved technology was demonstrated by the synthesis and characterization of five ODNs including three modified ones. The modified ODNs contained the electrophilic groups ethyl ester, α-chloroamide, and thioester. Using the technology, the sensitive groups can be installed at any location within the ODN sequences without using any sequence- or functionality-specific conditions and procedures.


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