NDLI: A novel class of glycosidase inhibitors: structures related to australine, lentiginosine, salacinol and swainsonine

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A novel class of glycosidase inhibitors: structures related to australine, lentiginosine, salacinol and swainsonine

Content Provider	Semantic Scholar
Author	Kumar, Nag S.
Copyright Year	2007
Abstract	This thesis focuses on the design and syntheses of the sulfonium-ion analogues of australine, lentiginosine, swainsonine, and other analogues of salacinol as potential glycosidase inhibitors, together with the investigation of their enzyme inhibitory activities . The syntheses of several bicyclic sulfonium-ion analogues of a naturally occurring glycosidase inhibitor, swainsonine, in which the bridgehead nitrogen atom is replaced by a sulfonium-ion, are described. These compounds were designed to test the hypothesis that a sulfonium salt carrying a penuanent positive charge would be an effective glycosidase inhibitor. We postulated that a permanent positive charge on the sulfur atom will mimic the highly unstable oxacarbenium ion transition state in a glycosidase-catalyzed hydrolysi s reaction. Screening of these compounds against Drosophila melanogaster Golgi-a-mannosidase II (dGMIl), an important mannosidase that is involved in the N-glycosylation pathway, showed that the configuration of the sulfonium-ion center is critical for activity and the design of new agents should incorporate this feature. The syntheses of eight s ulfonium compounds with structures related to the naturally OCCUlTing pyrrolizidine alkaloid, australine, in which the bridgehead nitrogen atom is replaced by a sulfonium-ion, are also described. The conformational preferences of these compounds, based on analysis of IH_I H vicinal coupling constants and 10NOESY data, are attributed to both steric and electrostatic interactions. These
File Format	PDF HTM / HTML
Alternate Webpage(s)	http://summit.sfu.ca/system/files/iritems1/8036/etd2919.pdf
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article

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