An inverse substrate orientation for the regioselective acylation of 3',5'-diaminonucleosides catalyzed by Candida antarctica lipase B?

@article{Lavandera2005AnIS,
  title={An inverse substrate orientation for the regioselective acylation of 3',5'-diaminonucleosides catalyzed by Candida antarctica lipase B?},
  author={Iv{\'a}n Lavandera and Susana Fern{\'a}ndez and Julia Magdalena and Miguel Ferrero and Romas J Kazlauskas and Vicente Gotor},
  journal={Chembiochem : a European journal of chemical biology},
  year={2005},
  volume={6 8},
  pages={
          1381-90
        }
}
  • Iván Lavandera, Susana Fernández, +3 authors Vicente Gotor
  • Published in
    Chembiochem : a European…
    2005
  • Chemistry, Medicine
  • Candida antarctica lipase B (CAL-B) catalyzes the regioselective acylation of natural thymidine with oxime esters and also the regioselective acylation of an analogue, 3',5'-diamino-3',5'-dideoxythymidine with nonactivated esters. In both cases, acylation favors the less hindered 5'-position over the 3'-position by upto 80-fold. Computer modeling of phosphonate transition-state analogues for the acylation of thymidine suggests that CAL-B favors acylation of the 5'-position because this… CONTINUE READING

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