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Hydrolytic Reactions of the cis-Methyl Ester of 3′-Deoxy-3′-thiothymidine 3′,5′-Cyclic(phosphorothiolate)

✍ Scribed by Mohamed I. Elzagheid; Kati Mattila; Mikko Oivanen; Bryan C. N. M. Jones; Richard Cosstick; Harri Lönnberg

Publisher
John Wiley and Sons
Year
2000
Tongue
English
Weight
255 KB
Volume
2000
Category
Article
ISSN
1434-193X

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✦ Synopsis

Hydrolysis of the cis-methyl ester of 3Ј-deoxy-3Ј-thiothymidine 3Ј-S,5Ј-O-cyclic(phosphorothiolate) (1a) has been followed by HPLC and MS. At pH Ͻ 2 hydrolysis of the thiophosphate triester moiety is acid-catalyzed (first order), while between pH = 2 and 5 the reaction is pH-independent and at pH Ͼ 5 first order in hydroxide ion. The uncatalyzed and acid-catalyzed reactions yield two thiophosphate diesters, the 3Ј-S,5Ј-O-cyclic phosphorothiolate 2 and 3Ј-S-phosphorothiolate methyl ester 3, in a 9:1 and 1:3 molar ratio, respectively. The hydroxide ion catalyzed reaction gives the

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