Syn glycosidic conformation

A syn glycosidic conformation is a base–sugar orientation in the syn region of the glycosidic torsion angle $\chi$. In the IUPAC-IUB convention the region is centered at $0^{\circ }$ and spans90degrees on either side. In a nonnegative360degree reporting interval, this region crosses the boundary: angles near both0 and360degrees belong to it.^[ref]

For an original example, $\chi =30^{\circ }$ and $\chi =330^{\circ }$ are both syn, because330degrees is equivalent to−30degrees. Their shortest angular separation is60degrees. Their ordinary arithmetic mean,180degrees, falls in the anti glycosidic conformation region and is therefore misleading as a mean orientation. Averaging their unit-circle vectors instead giveswhich points toward $\chi =0^{\circ }$.

The numerical convention is essential. Older choices using the base atom C8 for purines or C6 for pyrimidines can differ from the recommended glycosidic torsion angle by approximately180degrees. Comparing the same number under those two definitions could therefore appear to reverse a syn/anti assignment without any molecular motion.^[ref]

Syn is a local conformational descriptor. It is neither a statement that two bases are paired nor a label for the overall handedness of a nucleic-acid helix. Structural comparisons should retain the defining atoms and angle convention alongside the syn/anti label.