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The first 3′:5′‐cyclic nucleotide–amino acid complex: l‐His–cIMP

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In the crystal structure of the l‐His–cIMP complex, i.e.l‐histidinium inosine 3′:5′‐cyclic phosphate [systematic name: 5‐(2‐amino‐2‐carboxyethyl)‐1H‐imidazol‐3‐ium 7‐hydroxy‐2‐oxo‐6‐(6‐oxo‐6,9‐dihydro‐1H‐purin‐9‐yl)‐4a,6,7,7a‐tetrahydro‐4H‐1,3,5,2λ5‐furo[3,2‐d][1,3,2λ5]dioxaphosphinin‐2‐olate], C6H10N3O2 +┬ĚC10H10N4O7P, the Hoogsteen edge of the hypoxanthine (Hyp) base of cIMP and the Hyp face are engaged in specific amino acid–nucleotide (His...cIMP) recognition, i.e. by abutting edge‐to‐edge and by π–π stacking, respectively. The Watson–Crick edge of Hyp and the cIMP phosphate group play a role in nonspecific His...cIMP contacts. The interactions between the cIMP anions (anti/C3′–endo/transgauche/chair conformers) are realized mainly between riboses and phosphate groups. The results for this l‐His–cIMP complex, compared with those for the previously reported solvated l‐His–IMP crystal structure, indicate a different nature of amino acid–nucleotide recognition and interactions upon the 3′:5′‐cyclization of the nucleotide phosphate group.

Document Type: Research Article


Affiliations: Faculty of Chemistry, University of Wrocław, 14 Joliot-Curie St, 50-383 Wrocław, Poland

Publication date: 2012-08-15

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