Syntheses of d-ribosylamines, d-ribopyranosyl isothiocyanates, and d-ribopyranosylthioureas, and their transformations into heterocyclic compounds

Mota, J. Fuentes; Adrian, M.A. Pradera; Mellet, Carmen Ortiz; Fernández, José Manuel Garcı́a; Caballero, Reyes Babiano; Pérez, Juan Manuel Sánchez

doi:10.1016/s0008-6215(00)90798-5

Cited by 23 publications

(2 citation statements)

References 17 publications

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“…This attribution is consistent with the results of a 13 C NMR study on N‐phenyl‐D‐ribosylamines where the value of the chemical shift of the anomeric carbon C1’’ allowed to identify of the furanoid and the pyranoid form since a carbon resonates at lower fields in a 5‐term cycle than in a 6‐term cycle [27] . Based on the integration of the resonances of H1’’ protons, the ratio between pyranoid and furanoid isomers in D2O was ∼90 : 10 (Figure 2B), in agreement with the predomination of α‐ and β‐pyranose isomers observed both for ribose [28,29] and for N‐aryl‐aminoribose derivatives [27,30–32] …”

Section: Resultssupporting

confidence: 89%

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Are Two Riboses Better Than One? The Case of the Recognition and Activation of Adenosine Receptors

et al. 2023

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Traditionally, molecular recognition between the orthosteric site of adenosine receptors and their endogenous ligand occurs with a 1 : 1 stoichiometry. Inspired by previous mechanistic insights derived from supervised molecular dynamics (SuMD) simulations, which suggested an alternative 2 : 1 binding stoichiometry, we synthesized BRA1, a bis-ribosyl adenosine derivative, tested its ability to bind to and activate members of the adenosine receptor family, and rationalized its activity through molecular modeling.

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Section: Resultssupporting

confidence: 89%

“…[27] Based on the integration of the resonances of H1'' protons, the ratio between pyranoid and furanoid isomers in D2O was ~90 : 10 (Figure 2B), in agreement with the predomination of αand β-pyranose isomers observed both for ribose [28,29] and for N-aryl-aminoribose derivatives. [27,[30][31][32]…”

Section: Chemmedchemmentioning

confidence: 99%