Conformationally defined cyclohexyl carnitine analogs.

Academic Article

Abstract

  • Three diastereoisomers of racemic (3-carboxy-2-hydroxy-1-cyclohexyl)trimethylammonium chloride [C10H20NO3+.Cl-; (1S,2S,3S) (2), (1R,2S,3S) (3) and (1S,2R,3S) (4)] were designed as rigid analogs for different low-energy conformational states of carnitine [(1), (3-carboxy-2-hydroxy-1-propyl)trimethylammonium chloride]. Structures (2)-(4) all assume a chair conformation in the solid state, in which the bulky trimethylammonio group occupies the equatorial position. As such, the orientations about C2-C3 in (2), (3) and (4) are all essentially the same as that found for (1) in the solid state (torsion angles for C1-C2-C3-N1 near 180 degrees), while the orientations about C1-C2 in (2)-(4) are such that each diastereoisomer contains a different one of the three possible low-energy staggered conformations predicted for (1) in solution. Comparisons between (1) and (2)-(4) in the solid state revealed that diastereoisomers (2), (3) and (4) provide rigid models for the major low-energy conformations of carnitine.
  • Keywords

  • Carnitine, Crystallography, X-Ray, Models, Molecular, Molecular Conformation, Molecular Structure, Stereoisomerism
  • Pubmed Id

  • 15292319
  • Authorlist

  • Brouillette WJ; Gray GM; Saeed A
  • Start Page

  • 1160
  • End Page

  • 1164
  • Volume

  • 51 ( Pt 6)