posted on 2022-12-13, 18:06authored byYoung
Eum Hyun, Dnyandev B. Jarhad, Minjae Kim, Ayeon Yang, Gyudong Kim, Hong-Rae Kim, Lak Shin Jeong
The conformation of the central five-membered ring of
a nucleoside
plays an important role in enzyme recognition. Bicyclo[3.1.0]hexane,
also known as the methanocarba (MC), serves as a template that can
mimic the locked forms of the two distinctive conformations, namely,
the north and south conformations. While modified nucleosides locked
in the north conformation have been actively investigated, the south
counterpart remains largely unexplored because it is difficult to
synthesize. Herein, we report a concise synthetic route that can provide
the key amino sugar intermediate essential for the synthesis of (S)-MC ribonucleosides in a 100% stereoselective manner.
Also, through the proposed synthetic approach, we report the first
synthesis of enantiomerically pure (S)-MC cytidine 1. We believe our findings would greatly contribute to the
field of nucleoside chemistry and provide opportunities for novel
nucleoside discovery.