159701-87-8Relevant academic research and scientific papers
Fleetamine (3-O-α-d-glucopyranosyl-swainsonine): The synthesis of a hypothetical inhibitor of endo-α-mannosidase
Quach, Tim,Tsegay, Sammi,Thompson, Andrew J.,Kukushkin, Nikolay V.,Alonzi, Dominic S.,Butters, Terry D.,Davies, Gideon J.,Williams, Spencer J.
experimental part, p. 992 - 997 (2012/09/22)
3-O-α-d-Glucopyranosyl-swainsonine was originally proposed 17 as a potential inhibitor of the mammalian enzyme endo-α-mannosidase, but its synthesis has not been reported. Herein we report the total synthesis of this enigmatic compound, utilizing a halide-ion catalysed glycosylation of a swainsonine lactam with a glucosyl iodide donor as the key step. The resulting inhibitor was evaluated as an inhibitor of human endo-α-mannosidase, and as a ligand for bacterial orthologs from Bacteroides thetaiotaomicron and Bacteroides xylanisolvens, including active-centre variants, although no evidence for binding or inhibition was observed. The surprising lack of binding was rationalized by using structural alignment with an endo-α-mannosidase inhibitor complex, which identified deleterious interactions with the swainsonine piperidine ring and an essential active site residue. 2012 Elsevier Ltd.
Enantioselective Synthesis of Indolizidine Alkaloids: Formal Synthesis of (-)-Swainsonine and of (+)-Pumiliotoxin 251 D
Honda, Toshio,Hoshi, Michiyasu,Kanai, Kazuo,Tsubuki, Masayoshi
, p. 2091 - 2102 (2007/10/02)
Oxidative treatment of optically active 2-furylmethanol (furfuryl alcohol) derivative (R)-5, obtained by Sharpless kinetic resolution of the racemate, afforded the pyranone 9, which on successive reduction with lithium aluminium hydride in the presence of
