O-phospho-DL-threonine and O-phospho-L-threonine compared with their serine analogs

Acta Crystallogr C. 1996 Jul 15:52 ( Pt 7):1736-41. doi: 10.1107/s0108270195015708.

Abstract

In crystals of O-phospho-DL-threonine and O-phospho-L-threonine, the molecules are zwitterions HO3-POCH-(CH3)CH(NH3+)CO2H linked by three-dimensional networks of strong P-O-H...O = P, C-O-H...O = P, N-H...O = P and N-H...O = C hydrogen bonds with (O...O) = 2.55 (3) A and (N...O) = 2.84 (4) A. Both the molecular conformations and the nearest-neighbor hydrogen-bonded surroundings are very similar in the racemic and enantiomeric crystals of the threonine compounds, but earlier studies of crystals of the analogous serine compounds have shown that the serine zwitterions HO3-POCH2CH(NH3+)CO2H have different conformations about the C beta-O gamma-P phosphate ester bonds and different hydrogen-bonded surroundings.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Crystallization
  • Crystallography, X-Ray
  • Hydrogen Bonding
  • Models, Molecular
  • Molecular Conformation
  • Molecular Structure
  • Phosphoserine / chemistry*
  • Phosphothreonine / chemistry*

Substances

  • Phosphothreonine
  • Phosphoserine