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Original Articles

SYNTHÈSE D'ANALOGUES DE GLUCOSE-6 PHOSPHATE, INHIBITEURS POTENTIELS D'sHEXOKINASE

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Pages 71-80 | Received 06 Jun 1990, Accepted 19 Jul 1990, Published online: 23 Sep 2006
 

Abstract

Des analogues de glucose-6-phosphate porteurs en position 6 d'un groupement ester, thio-ester, thio-phosphate, thio-phosphoroamidate ou phosphonate. ont été synthétisés à partir de chlorophosphites ou par réaction d'Arbuzov. Dans les cas autres que phosphonate, les possibilités de migration d'un groupe OH à un autre du glucose ont été considérées. Aucun réarrangement n'est observé lors du déblocage des groupements protecteurs en milieu fortement basique, ni lors d'un traitement acide nécessaire à la purification. Les tests d'inhibition montrent que les meilleurs résultats sont obtenus avec des structures de type thiophosphoroamidate.

Analogues of glucose-6-phosphate bearing at position 6, an ester group. thio-ester, thio-phosphate. thio-phosphoro-amidate or phosphonate were synthesized starting from chlorophosphite or by Arbuzov type reaction. For groups other than phosphonate, possible migrations from an OH group to another on glucose have been considered. In no case such a migration is observed particularly during work-up in either strongly basic or in acidic conditions required for purification. Inhibition tests indicate that the best results are obtained with thio-phosphoroamidates.

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