New concept for the separation of an anomeric mixture of alpha/beta-D-nucleosides through regioselective enzymatic acylation or hydrolysis processes.
An efficient and high yield protocol for the synthesis and separation of 3'- and/or 5'-protected alpha-2'-deoxynucleosides has been developed through regioselective acylation/deacylation processes catalyzed by enzymes. Pseudomonas cepacia lipase (PSL-C) was found to be highly chemo- and regioselective toward the 3'-position of the beta-2'-deoxynucleoside derivatives, whereas PSL-C displayed opposite selectivity toward the 5'-position for the corresponding alpha-anomer. The successful application of this protocol was demonstrated by a convenient separation of an alpha/beta-mixture of thymidine derivatives from an industrial waste stream. Furthermore, this technique was also applied for the separation of an anomeric mixture of 2'-deoxy-2'-fluoro-alpha/beta-arabinonucleosides that are useful building blocks for the antisense constructs.
García
Javier
J
Departamento de Química OrgAnica e InorgAnica and Instituto Universitario de Biotecnología de Asturias, Universidad de Oviedo, 33006-Oviedo (Asturias), Spain.
Díaz-Rodríguez
Alba
A
Fernandez
Susana
S
Sanghvi
Yogesh S
YS
Ferrero
Miguel
M
Gotor
Vicente
V
D000215:Acylation; D002236:Carbohydrate Conformation; D006868:Hydrolysis; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D009705:Nucleosides