کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
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1356348 | 981111 | 2010 | 7 صفحه PDF | دانلود رایگان |
The syntheses of an isomer of kotalanol, a naturally occurring glucosidase inhibitor, and of kotalanol itself are described. The target compounds were synthesized by nucleophilic attack of PMB-protected 1,4-anhydro-4-thio-d-arabinitol at the least hindered carbon atom of two 1,3-cyclic sulfates, which were synthesized from d-mannose. Methoxymethyl ether and isopropylidene were chosen as protecting groups. The latter group was critical to ensure the facile deprotection of the coupled products in a one-step sequence to yield kotalanol and its isomer. The stereoisomer of kotalanol, with the opposite stereochemistry at the C-6′ stereogenic centre, inhibited the N-terminal catalytic domain of intestinal human maltase glucoamylase (ntMGAM) with a Ki value of 0.20 ± 0.02 μM; this compares to a Ki value for kotalanol of 0.19 ± 0.03 μM. The results indicate that the configuration at C-6′ is inconsequential for inhibitory activity against this enzyme.
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Journal: Bioorganic & Medicinal Chemistry - Volume 18, Issue 8, 15 April 2010, Pages 2829–2835