Absolute configuration of strictosidinic acid

Acta Crystallogr C. 2012 Apr;68(Pt 4):m94-6. doi: 10.1107/S0108270112010372. Epub 2012 Mar 14.

Abstract

The absolute configuration of strictosidinic acid, (2S,3R,4S)-3-ethenyl-2-(β-D-glucopyranosyloxy)-4-{[(1S)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]methyl}-3,4-dihydro-2H-pyran-5-carboxylate, was determined from its sodium chloride trihydrate, poly[[diaqua((2S,3R,4S)-3-ethenyl-2-(β-D-glucopyranosyloxy)-4-{[(1S)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-2-ium-1-yl]methyl}-3,4-dihydro-2H-pyran-5-carboxylate)sodium] chloride monohydrate], {[Na(C(26)H(32)N(2)O(9))(H(2)O)(2)]Cl·H(2)O}(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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbolines / chemistry*
  • Glycosides / chemistry*
  • Models, Molecular
  • Molecular Conformation

Substances

  • Carbolines
  • Glycosides
  • strictosidinic acid