title: The first 3':5'-cyclic nucleotide-amino acid complex: L-His-cIMP.
abstract: 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-1,3,5,2λ(5)-furo[3,2-d][1,3,2λ(5)]dioxaphosphinin-2-olate], C(6)H(10)N(3)O(2)(+)·C(10)H(10)N(4)O(7)P(-), 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/trans-gauche/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.
authors.affiliation: Faculty of Chemistry, University of Wrocław, Poland. katarzyna.slepokura@chem.uni.wroc.pl
authors.forename: Katarzyna
authors.initials: K
authors.lastname: Slepokura
mesh_terms: D000598:Amino Acids, Cyclic; D018360:Crystallography, X-Ray; D007289:Cyclic IMP / Q000737:chemistry*; D008958:Models, Molecular; D009712:Nucleotides, Cyclic / Q000737:chemistry*
chemical_list: D000598:Amino Acids, Cyclic; D009712:Nucleotides, Cyclic; D007289:Cyclic IMP