Cytosine-(2-carboxyethyl)-1-yl-L-asparagine, monohydrate

Date: Dec.1999

This structer was produced by Tep2Rotater,
and stucked by GifBuilder 0.5 (Yves Piguet, 1997)

ORTEP-III (Burnett, 1996) drawing

Photo of crystal used for data collection.

Integration of the amino acid and the nucleic base has produced probes having outstanding properties to investigate the molecular recognition, and it is, for example, well known that the peptidic nucleic acids make thermostable complexes with DNA1. In our serial studies,2,3 the cooperation of the amino acids and the nucleic acids has been attempted to design the molecules which interact with the certain nucleic base, and the structures of the hybrid dipeptides including the cytosine base have been analyzed. In this paper, the structure of cytosine-hybrid dipeptide including L-asparagine (Fig.1) is reported. The title compound (C-Asn) was synthesized from 1-(2-carboxyethyl)-cytosine and asparagine methyl ester. After trials of the crystallization by changing the solvent conditions, only an aqueous methanol solution gave small crystals with the dimension of mm3. These crystals insufficiently diffracted X-ray on the Rigaku RU200 generator. Intensity data was, therefore, measured on a synchrotron, SPring-8/BL24XU-A. The crystal and experimental data are listed in Table 1.

Paper: Crystal Structure of Cytosine Hybrid Dipeptide, Cytosine-(2-carboxyethyl)-1-yl-L-asparagine
Mitsunobu DOI, Akiko ASANO1, Toshimasa ISHIDA, Masahiro SASAKI, Masamichi NAKAI, Hiroshi HASEGAWA, Yoshio KATSUYA, Yoshihiro MEZAKI, Taizo TANIGUCHI and Akira TERASHIMA
Analytical Sciences, , in submission (2000)

X-Ray Data Summary
formulaC11H15N5O5, H2O
weight 315.30
symmetry orthorhombic
space group P212121
Cell Crystal
a 17.9558(16) Ang. description needle
b 22.8603(19) Ang. colour Colorless
c 4.9591(2) Ang. size (mm) 0.25x0.05x0.05
alpha 90.0 deg. Dx (g/ml) 1.029
beta 90.0 deg. F(000) 664
gamma 90.0 deg. mu(CuKa) 0.085
volume 2035.6(3) Ang^3 wave length0.834 A
Z 4 temperature253(2)
Diffrn measurementRefinementspace
device type Rigaku RAXIS-4 Flack -0.2(19)
radiation source SPring-8/BL24XU-A* parameters 210
index limit 0~h~22, 0~k~28, -5~L~5 restraints 0
theta (deg.) 3.41-31.41 R_factor_gt 0.0797
total reflections 3194 wR_factor_gt 0.2053
reflections(obs) 3086 .gt. 2sigma(I) dela rho_max 0.573 e A^3
Structure delta rho_min -0.233 e A^3
solution SHELXL-97 shift/su_maxlt.0.001
refinementSHELXL-97 Goodness of fit 1.009
*The machine time of the synchrotron was given from Hyogo prefecture and Japan Synchrotron Radiation Research Institute with the proposal No. C99A24XU-005N.
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