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Absolute configuration of strictosidinic acid
Authors:Rosane de P Castro  Carolina da S Matos  Cludia A do Nascimento  Cecília M A Oliveira  Lucília Kato  Luciano M Lio  Jos R Sabino
Abstract:The absolute configuration of strictosidinic acid, (2S,3R,4S)‐3‐ethenyl‐2‐(β‐d ‐glucopyranosyloxy)‐4‐{(1S)‐2,3,4,9‐tetrahydro‐1H‐pyrido3,4‐b]indol‐1‐yl]methyl}‐3,4‐dihydro‐2H‐pyran‐5‐carboxylate, was determined from its sodium chloride trihydrate, polydiaqua((2S,3R,4S)‐3‐ethenyl‐2‐(β‐d ‐glucopyranosyloxy)‐4‐{(1S)‐2,3,4,9‐tetrahydro‐1H‐pyrido3,4‐b]indol‐2‐ium‐1‐yl]methyl}‐3,4‐dihydro‐2H‐pyran‐5‐carboxylate)sodium] chloride monohydrate], {Na(C26H32N2O9)(H2O)2]Cl·H2O}n. The strictosidinic acid molecule participates in intermolecular hydrogen bonds of the O—H...O and O—H...Cl types. The solid‐state conformation was observed as a zwitterion, based on a charged pyridine N atom and a carboxylate group, the latter mediating the packing through coordination with the sodium cation.
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