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The first 3':5'-cyclic nucleotide-amino acid complex: L-His–cIMP.
Autorzy
Rok wydania
2012
Czasopismo
Acta Crystallographica Section C: Structural Chemistry
Numer woluminu
C68
Strony
o311-o316
DOI
10.1107/S0108270112030041
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
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+·C10H10N4O7P−, 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.
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