Ilse Verheggen

Properties of oligonucleotides with six membered carbohydrate mimics and a 1,4-relationship between the base moiety and the hydroxymethyl group

Abstract The properties of oligonucleotides with a six-membered carbohydrate mimic in the backbone structure and a 1,4-relationship between the base moiety and the hydroxymethyl group are summarized. The different six-membered rings that were studied are: 1,5-anhydro-2,3-dideoxy-D-arabino-hexitol, 1,5-anhydro-2-deoxy-D-mannitol, 1,5-anhydro-2-deoxy-D-altritol and 3-hydroxy-4-hydroxymethyl-cyclohexane.

Synthesis of nucleoside analogues with a 1,5-anhydrohexitol moiety

Abstract Glucose after conversion to a 3-deoxy-1,5-anhydro-D-glucitol moiety, was coupled at its 2-position to heterocyclic bases either by nucleophilic displacement or under Mitsunobu reaction conditions to afford new nucleoside analogues with a 1,5-anhydrohexitol moiety.

Synthesis of 1,5-Anhydro-2-(N 6-Cyclopentyladenin-9-Yl)-2-Deoxy-D-Altrohexitol

Abstract The N 6-cyclopentyladenosine (CPA) analogue (4) was synthesized in 10 steps starting from glucose. The results of the radioligand binding assays are consistent with the thus far published findings that compounds containing a six-membered moiety at N 9 exhibit extremely weak affinity for adenosine receptors. Replacement of the ribofuranosyl moiety of CPA (2) by a 2-deoxy-D-altrohexitol moiety is sufficient to completely abolish its agonist activity.

Synthesis of 1,5-Anhydrohexitol Nucleosides as Mimics of AZT, D4T and DDC +

Abstract 1,5-Anhydrohexitol congeners of AZT, D4T and DDC were synthesized. These compounds did not show anti-HIV activity. +Dedicated to Professor Yoshihisa Mizuno on the occasion of his 75th birthday.