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.
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.
Doi
Mitsunobu
M
Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan. doit@gly.oups.ac.jp
Nakamoto
Yasuhiko
Y
Asano
Akiko
A
D002104:Cadmium / Q000737:chemistry; D018360:Crystallography, X-Ray; D003596:Cytosine / Q000031:analogs & derivatives* / Q000737:chemistry*; D004151:Dipeptides / Q000737:chemistry*; D005583:Fourier Analysis; D006860:Hydrogen Bonding; D007202:Indicators and Reagents; D008239:Lysine / Q000031:analogs & derivatives* / Q000737:chemistry; D008958:Models, Molecular; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000737:chemistry; D012694:Serine / Q000031:analogs & derivatives* / Q000737:chemistry
D004151:Dipeptides; D007202:Indicators and Reagents; C515322:N-(2-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)propionyl)lysine; C515320:N-(2-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)propionyl)phenylalanine; C515321:N-(2-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)propionyl)serine; D002104:Cadmium; D012694:Serine; D010649:Phenylalanine; D003596:Cytosine; D008239:Lysine