Cytosine-containing hybrid dipeptides: N-[2-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)propionyl]-L-phenylalanine N-[2-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)propionyl]-L-serine monohydrate and N-[2-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)propionyl]-L-lysine

Acta Crystallogr C. 2005 Oct;61(Pt 10):m577-82. doi: 10.1107/S0108270105026259. Epub 2005 Sep 10.

Abstract

The title compounds are cytosine-incorporating hybrid dipeptides showing affinities for 9-ethyl-7-methylguanine (7mG). Four molecules of the L-phenylalanine (L-Phe) derivative, C16H14N4O4, are present in the asymmetric unit, with similar folded conformations but with slightly different torsion angles involving the L-Phe group. The L-serine (L-Ser) derivative crystallizes as a monohydrate, C10H14N4O5.H2O, the two independent molecules having extended conformations, whereas the two independent molecules of the L-lysine (L-Lys) system in the final compound, C13H21N5O4, are folded. The cytosine-cytosine base pair (pyrimidine NN interactions) was observed only for the L-lysine derivative. Conformational comparisons with previous structures of cytosine hybrid dipeptides may show the relationships between side-chain position and binding phases for 7mG.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cadmium / chemistry
  • Crystallography, X-Ray
  • Cytosine / analogs & derivatives*
  • Cytosine / chemistry*
  • Dipeptides / chemistry*
  • Fourier Analysis
  • Hydrogen Bonding
  • Indicators and Reagents
  • Lysine / analogs & derivatives*
  • Lysine / chemistry
  • Models, Molecular
  • Phenylalanine / analogs & derivatives*
  • Phenylalanine / chemistry
  • Serine / analogs & derivatives*
  • Serine / chemistry

Substances

  • Dipeptides
  • Indicators and Reagents
  • N-(2-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)propionyl)lysine
  • N-(2-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)propionyl)phenylalanine
  • N-(2-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)propionyl)serine
  • Cadmium
  • Serine
  • Phenylalanine
  • Cytosine
  • Lysine