Glycosidase inhibitory properties

Sifferlen, T, Defoin, A, Streith, J, Le Noven, D, Tamus, C, Dosbaa, I, Foglietti, M-J, Chiral 5-methyl-trihydroxypyrrolidines. Preparation from 1,2-oxazines and glycosidase inhibitory properties. Tetrahedron, 56, 971-978, 2000. 

The glycosidase-inhibitory properties of sugar-shaped cyclic thioureas were first, explored by Lehmann and co-workers,414 who obtained the hexa-hydropyrimidine-2-thione glucomimetic 271 by thiocarbonylation of the diamine precursor 270. Compound 271 was a very weak inhibitor of sweet-almond /3-glucosidasc, and this was ascribed to the lack of the OH group at the homologous position of C-3 in n-glucopyranosidcs. Moreover, an unexpected preference for the irons-diaxial conformation in deuterium oxide solution. was observed (Scheme 73). 

Glycosylimino-oxazolines such as the a-D-mannosylimino-derivative 33 have been prepared as further analogues of trehazoline, and their glycosidase inhibitory properties determined. Reaction of the glucofurano-isoxazole 34 with amines is known to cause displacement of the thiobenzyl substituent, but it has now been found that unsaturated derivatives such as 35 can be the products formed under forcing conditions (Scheme 6). ... 

The synthesis and glycosidase inhibitory properties of several nitrogen-in-the-... 

Natural Products. Four new broussonetines, M, O, P and Q (106-109), pyrrolidine alkaloids with p-glycosidase inhibitory properties, have been isolated from branches of Broussoneta kazinokiP... 

A preparation of l,5-dideoxy-l,S-imino-D-allitol from A protected deoxynqjirimycin v ch involves a microbial redox reaction at C-3 has been described, and the glycosidase inhibitory properties of the product were determined together with those of other imino-alditols isolated from the leaves of Mens alba (see also ref 40 above). ... 

L-Ribose derivative 244 undergoes addition by l-lithio-2-iV-tritylimidazole to give 245, which is then converted to fused imidazole 246 and thence to amino sugar analogue 247 (R=NHAc, OH), which shows glycosidase inhibitory properties (Scheme 42). ... 

J. Calveras, M. Egido-Gabas, L. G6mez, I. Casas, T. Parella, I. loglar, I. Bujons, P. Clap, Dihydroxyacetone phosphate aldolase-catalyzed synthesis of structurally diverse polyhy-droxylated pyrrolidine derivatives and evaluation of their glycosidase inhibitory properties, Chem. Eur. J. 15 (2009) 7310-7328. 

Morusimic acid B was first isolated together with five new unknown nortropane alkaloids and five other new amino acids by Kusano et al. in 2002 from the ripened fruits of the white Mulberry tree (Moms alba L, Moracae). Several compounds isolated from Moms alba show glycosidase inhibitory properties. 

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