Chemistry and biodiversity (2017)
Update date:2022-08-11
Topics:
Kiuru, Emilia
Malmikare, Suvi
Ora, Mikko
Protected dinucleoside-2′,5′-monophosphate has been prepared to develop a prodrug strategy for 2-5A. The removal of enzymatically and thermally labile 4-(acetylthio)-2-(ethoxycarbonyl)-3-oxo-2-methylbutyl phosphate protecting group and enzymatically labile 3′-O-pivaloyloxymethyl group was followed at pH 7.5 and 37?°C by HPLC from the fully protected dimeric adenosine-2′,5′-monophosphate 1 used as a model compound for 2-5A. The desired unprotected 2′,3′-O-isopropylideneadenosine-2′,5′-monophosphate (9) was observed to accumulate as a major product. Neither the competitive isomerization of 2′,5′- to a 3′,5′-linkage nor the P–O5′ bond cleavage was detected. The phosphate protecting group was removed faster than the 3′-O-protection and, hence, the attack of the neighbouring 3′-OH on phosphotriester moiety did not take place.
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