TY - JOUR
AU - Fischer, Bilha
AB - 7‐membered cyclic nucleotides have remained unknown despite the natural abundance of their 5‐ and 6‐membered counterparts. Here, we report the first synthesis of 2′,3′‐cyclic nucleosides (tetrathio)diphosphonate (2′,3′‐cNTDPs) by a rapid one‐step, regioselective, and protection‐free reaction of U, A, C, I, and G, with methylene‐bis(1,3,2‐dithia‐phospholane‐2‐sulfide) (DTPS). The reaction proceeds instantaneously, even at ‐35 °C, resulting in the quantitative conversion of methylene‐bis‐DTPS. Density functional theory (DFT) calculations of ∆Gr confirm the synthetic feasibility and regioselectivity, attributing the efficiency to strain release in DTPS rings and entropic gain from thiirane elimination. The resulting 2′,3′‐cNTDPs exhibited remarkable hydrolytic stability and greater solution structural rigidity than free nucleosides.
TI - Innovative Cyclic Nucleotides – Nucleoside 2′,3′‐Seven‐Membered Cyclic Diphosphonate Derivatives. Theoretical Feasibility, Synthesis, and Properties
JF - Chemistry - A European Journal
DO - 10.1002/chem.202501228
DA - 2025-06-26
UR - https://www.deepdyve.com/lp/wiley/innovative-cyclic-nucleotides-nucleoside-2-3-seven-membered-cyclic-aR104dbTrQ
VL - 31
IS - 36
DP - DeepDyve
ER -