Glycosidase Inhibition by cyclic sulfonium compounds

Sulfonium ions as inhibitors of the mycobacterial galactofuranosyltransferase GlfT2

“…Similarly, 1-bromo-2-phenylethane (41) was converted into compound 63 in modest (32%) yield. As shown, the coupling reactions gave mixtures of R/S stereoisomers, which was expected [46][47][48] given the lack of substituents at the carbons adjacent to the sulfur. Such groups would be anticipated to inuence the stereochemistry of the reaction.…”

Synthesis of analogues of salacinol containing a carboxylate inner salt and their inhibitory activities against human maltase glucoamylase

“…1) have been isolated from Salacia reticulata WIGHT, 3,4 and Salacia oblonga and Salacia chinensis, 5 traditionally used in the Ayurvedic system of India and Sri Lanka for the treatment of diabetes. 6 The sulfonium ion structure of these compounds has stimulated different groups to carry out the synthesis of salacinol, 7,8 and other carbohydrate-based cyclic sulfonium compounds, [9][10][11][12][13][14][15] such as 3 11 and 4 ( Fig. 2), 12 as a new class of glycosidase inhibitors.…”

“…The fact that salacinol has greater inhibitory activity and specificity against a-glucosidases than the methyl sulfonium ion (3) indicates that the hydroxyl groups on the acyclic chain and/or the sulfate group are advantageous. 18 Yuasa et al 19 reported that docking of salacinol into the binding site of glucoamylase indicated close contacts between the sulfate ion with Arg305. Crystallographic analysis of the interactions of Drosophila melanogaster Golgi a-mannosidase II with salacinol and its analogues also shows that the sulfate group does interact with residues in the enzyme active site.…”

Isolation and Characterization of α-Glucosidase Inhibitor Produced by Bacillus sp. SKU31-1 Strain

“…α-Glucosidase 저해제를 개발하기 위한 방법으로 화학적 합성, 천연물에서 분리와 미생물에 의한 생산 등을 들 수 있다. 화학합성에 의해 Sulfonamide (Yuasa et al, 2001) xanthone 유 도체 등의 물질이 보고되었으나 간질환과 소화계 이상 등 부정 적인 증상을 나타내고 (Fowler, 2007) H COSY spectra 분석과 문헌조사를 통해 5-amino-1-hydroxymethyl-1,2,3,4-cyclohexanetetrol 로 동정되었다. Compound K의 α-glucosidase 저해 활성은 IC50 값이 maltose 기질에서는 1.9 μM이고, sucrose 기질 사용시 4.9 mM 이었다.…”