کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1390845 1500905 2007 9 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Synthesis of phosphate derivatives related to the glycosidase inhibitor salacinol
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Synthesis of phosphate derivatives related to the glycosidase inhibitor salacinol
چکیده انگلیسی

The syntheses of polyhydroxylated imino- and anhydro thio-alditol compounds related to the naturally occurring glycosidase inhibitor, salacinol, containing a phosphate group in the side chain are described. The compounds lack hydroxyl groups on the acyclic side chain and are prototypes of the exact salacinol analogue. The synthetic strategy relies on the Mitsunobu reaction of N- and S-hydroxyalkyl derivatives of 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-imino-d-arabinitol and 1,4-anhydro-2,3,5-tri-O-benzyl-1-thio-d-arabinitol with dibenzyl phosphate to yield the corresponding protected heteroalditol phosphates. Screening of these compounds against recombinant human maltase glucoamylase (MGA), a critical intestinal glucosidase involved in the processing of oligosaccharides of glucose into glucose itself, shows that they are not effective inhibitors of MGA and demonstrates the importance of the hydroxyl and/or sulfate substituents present on the side chain for effective inhibition. The attempted synthesis of the exact analogue of salacinol by opening of cyclic phosphates is also described.

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ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Carbohydrate Research - Volume 342, Issues 12–13, 3 September 2007, Pages 1934–1942
نویسندگان
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