cADPR Analogues:  Effect of an Adenosine 2‘- or 3‘-Methoxy Group on Conformation

Abstract

[structure: see text] The 2'-OMe-A (2) and 3'-OMe-A (3) analogues of the calcium release agent cADPR (1) were prepared and their solution structures studied by NMR spectroscopy. Compared to 1, 2 shows a shift in its A ring conformation and changes in its R ring N:S and gammat:gamma+ ratios, while 3 displays a significant change in the conformation of its A ring gamma-bond.

Dinucleoside polyphosphates act as 5′-RNA caps in bacteria

“…Solids were dried overnight under vacuum and used in the next step without further purification. MS (ESI + ) m/z (%): 500 (25,+Na), 522 (100, +2Na), 544 (40,+3Na). HRMS (ESI) m/z: [M+Na + ] (C 13 H 17 O 9 N 7 NaP 2 ) calc.…”

An iodocyclization approach toward diastereoselective synthesis of highly functionalized tetrasubstituted tetrahydrofurans with 2,5-trans and 2,5-cis relationships from pyranoside derived acyclic oximes

“…Here, in its 1 H NMR spectra the signals for H 4 20 is greater than 90°and therefore, the stereostructure of this isomer could be assigned as 7c (Fig. 2).…”

Design, Synthesis, and Chemical and Biological Properties of Cyclic ADP-4-Thioribose as a Stable Equivalent of Cyclic ADP-Ribose

“…One difference between cADPR and cADPcR is their p K a values for protonation at the N 6 -position. The p K a of cADPcR (8.9)5d is somewhat higher than that of cADPR (8.3),8b which might affect its interaction with target proteins. Under physiological conditions, cADPR is in a mixture of the protonated amino form and the deprotonated imino form, where most of cADPcR should be present in the amino-form due to its relatively higher p K a .…”

“…cADPR is in an equilibrium between the N 6 -protonated amino-form and the N 6 -deprotonated imino-form, as shown in Figure 2 8. One difference between cADPR and cADPcR is their p K a values for protonation at the N 6 -position.…”