Synthesis of aza- and thia-spiroheterocycles and attempted synthesis of spiro sulfonium compounds related to salacinol.

Synthesis of aza- and thia-spiroheterocycles and attempted synthesis of spiro sulfonium compounds related to salacinol. Research Abstract Details 

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Synthesis of aza- and thia-spiroheterocycles and attempted synthesis of spiro sulfonium compounds related to salacinol. Abstract Text:

Wang Chen,B Mario Pinto,Wang Chen,B Mario Pinto,

The synthesis of aza- and thia-spiroheterocycles and the attempted synthesis of spiro sulfonium compounds related to salacinol are described. The binding of the nanomolar inhibitor swainsonine to Drosophila Golgi alpha-mannosidase II (dGMII) involves a large contribution of interactions between the six-membered ring of the inhibitor and the hydrophobic pocket within the enzyme active site. Salacinol, a naturally occurring sulfonium ion, is one of the active principles in the aqueous extracts of Salacia reticulata that are traditionally used in Sri Lanka and India for the treatment of diabetes. Spiro aza- and thia-heterocycles and a spiro analogue of salacinol were designed with the expectation that the hydrocarbon portions would make hydrophobic contributions to binding. The former sets of compounds were synthesized successfully but the salacinol analogue proved to be elusive. The stereochemistry of the final compounds was determined by means of 1D-NOESY experiments. The aza- and thia-heterocycles were not effective inhibitors of Golgi alpha-mannosidase II or human maltase glucoamylase.

Synthesis of aza- and thia-spiroheterocycles and attempted synthesis of spiro sulfonium compounds related to salacinol. Publishing Authors By Initials

W Chen,BM Pinto,W Chen,BM Pinto,

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Synthesis of aza- and thia-spiroheterocycles and attempted synthesis of spiro sulfonium compounds related to salacinol. Journal Published:

PUBLICATION TYPE: Research Support, Non-U.S. Gov

Journal: Carbohydrate research

VOLUME: 342

Page Numbers: 2163-72

Journal Abbreviation: Carbohydr. Res.

ISSN: 0008-6215

DAY: 13

MONTH: 07

YEAR: 2007

Synthesis of aza- and thia-spiroheterocycles and attempted synthesis of spiro sulfonium compounds related to salacinol. Information

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LANGUAGE: eng

NlmUniqueID: 43535

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Grant and Affiliation Information for Synthesis of aza- and thia-spiroheterocycles and attempted synthesis of spiro sulfonium compounds related to salacinol.

AFFILIATION: Department of Chemistry, Simon Fraser University, Burnaby, British Columbia, Canada V5A 1S6.

Country: Netherlands

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MEDLINETA: Carbohydr Res

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