Original scientific paper

Crystal and Molecular Structure of (4S,5S)-6-Ammonium-6-deoxy-3-O-ascorbate

Biserka Kojić-Prodić ; Ruđer Bošković Institute, P.O.B. 1016, 41001 Zagreb, Croatia
Željko Danilović ; Ruđer Bošković Institute, P.O.B. 1016, 41001 Zagreb, Croatia
Vitomir Puntarec ; Ruđer Bošković Institute, P.O.B. 1016, 41001 Zagreb, Croatia
Sanja Tomić ; Ruđer Bošković Institute, P.O.B. 1016, 41001 Zagreb, Croatia
Božidar Šušković ; Research Institute PLIVA, Zagreb, Croatia

Abstract

The antitumor activity of 6-bromo-6-deoxy-L-ascorbic acid (Osmak et aL, Res. Exp. Med. 190, (1990) 443) initiated research of other C6-derivatives and the title molecule, which has been structurally characterized by X-ray diffraction methods. Molecular dynamics and semiempirical approaches have been used to evaluate side chain conformations. In the ciystalline state the molecule appears as a zwitterion formed by dissociation of the proton at 03. The y-lactone ring exhibits a twisted lTa conformation. The enediole and the lactone groups are not planar. Molecular packing is dominated by a three-dimensional hydrogen bond network via N-H—O and O-H—O interactions. The structure is refined to an# = 0.052 [FQ > 4a (F0)] using low temperature data [103(3) K)

Keywords

Hrčak ID:

137287

URI

https://hrcak.srce.hr/137287

Publication date:

31.12.1991.

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