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

• Published in: Acta crystallographica. Section C, Crystal structure communications Crystal structure communications, 2006-07, Vol.62 (7), p.o405-o409
• Main Authors: Ślepokura, Katarzyna, Lis, Tadeusz, Bogucka, Małgorzata, Lutomska, Joanna, Kraszewski, Adam, Sierosławski, Krzysztof
• Format: Article
• Language: English
• Subjects: Chemical compounds; Condensed matter: structure, mechanical and thermal properties; Crystal structure; Crystalline state (including molecular motions in solids); Exact sciences and technology; Organic chemistry; Physics; Structure of solids and liquids; crystallography; Structure of specific crystalline solids; Theory of crystal structure, crystal symmetry; calculations and modeling
• ISSN: 0108-2701; 1600-5759
• DOI: 10.1107/S0108270106017811

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—H⋯O, N—H⋯X and C—H⋯X (X = O or N) hydrogen‐bond contacts, characterize (I) and (II), respectively.