First synthesis of fully modified 4'-selenoRNA and 2'-OMe-4'-selenoRNA based on the mechanistic considerations of an unexpected strand break.
Org Lett
; 16(18): 4710-3, 2014 Sep 19.
Article
in En
| MEDLINE
| ID: mdl-25181546
ABSTRACT
This study investigated oligonucleotide (ON) synthesis containing 4'-selenoribonucleoside(s) under standard phosphoramidite conditions. Careful operation using a manual ON synthetic system revealed that an unexpected strand break occurred to afford a C2-symmetric homodimer as a byproduct. In addition, this side reaction occurred during I2 oxidation. On the basis of these findings, the first synthesis of fully modified 4'-selenoRNA and 2'-OMe-4'-selenoRNA was achieved using tert-butyl hydroperoxide (TBHP) as the alternative oxidant.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Oligonucleotides
/
Organometallic Compounds
/
Selenium
/
RNA
/
Tert-Butylhydroperoxide
Language:
En
Journal:
Org Lett
Journal subject:
BIOQUIMICA
Year:
2014
Document type:
Article
Affiliation country:
Japan