Acta Crystallographica Section C

Crystal Structure Communications

Volume 62, Part 7 (July 2006)

organic compounds

fg3019 scheme

Acta Cryst. (2006). C62, o405-o409 [ doi:10.1107/S0108270106017811 ]

Different nucleobase orientations in two cyclic 2',3'-phosphates of purine ribonucleosides: Et₃NH(2',3'-cAMP) and Et₃NH(2',3'-cGMP)·H₂O

K. Sieroslawski, K. Slepokura, T. Lis, M. Bogucka, J. Lutomska and A. Kraszewski

Abstract: The crystal structures of triethylammonium adenosine cyclic 2',3'-phosphate {systematic name: triethylammonium 4-(6-aminopurin-9-yl)-6-hydroxymethyl-2-oxido-2-oxoperhydrofurano[3,4-c][1,3,2]dioxaphosphole}, Et₃NH(2',3'-cAMP) or C₆H₁₆N⁺·C₁₀H₁₁N₅O₆P^-, (I), and guanosine cyclic 2',3'-phosphate monohydrate {systematic name: triethylammonium 6-hydroxymethyl-2-oxido-2-oxo-4-(6-oxo-1,6-dihydropurin-9-yl)perhydrofurano[3,4-c][1,3,2]dioxaphosphole monohydrate}, [Et₃NH(2',3'-cGMP)]·H₂O or C₆H₁₆N⁺·C₁₀H₁₁N₅O₇P^-·H₂O, (II), reveal different nucleobase orientations, viz. anti in (I) and syn in (II). These are stabilized by different inter- and intramolecular hydrogen bonds. The structures also exhibit different ribose ring puckering [₄E in (I) and ³T₂ in (II)] and slightly different 1,3,2-dioxaphospholane ring conformations, viz. envelope in (I) and puckered in (II). Infinite ribbons of 2',3'-cAMP^- and helical chains of 2',3'-cGMP^- ions, both formed by O-HO, N-HX and C-HX (X = O or N) hydrogen-bond contacts, characterize (I) and (II), respectively.

Formula: C₆H₁₆N⁺·C₁₀H₁₁N₅O₆P^- and C₆H₁₆N⁺·C₁₀H₁₁N₅O₇P^-·H₂O


	Structure factor file (CIF format) (191.7 kbytes) [ doi:10.1107/S0108270106017811/fg3019Isup2.hkl ] Contains datablock I

	Structure factor file (CIF format) (339.7 kbytes) [ doi:10.1107/S0108270106017811/fg3019IIsup3.hkl ] Contains datablock II

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