An efficient and mild access to N-acetyl protected purine nucleosides based on a chemoselective enzymatic hydrolysis

Authors
Palacio, Cyntia M.; Sabaini, María Belén; Iribarren, Adolfo Marcelo; Iglesias, Luis Emilio
Publication Year
2013
Language
English
Format
article
Status
Published version
Description
N-Monoacetylated derivatives of ribo- (adenosine, guanosine) and 2′-deoxyribonucleosides (2′-deoxyadenosine and 2′-deoxyguanosine), useful as oligonucleotide building blocks, were obtained in 88–100% by enzymatic chemoselective hydrolysis of the corresponding peracetylated nucleosides. Among the tested hydrolases, most satisfactory results were found with acylase I from Aspergillus melleus and Candida antarctica lipase B. For acylase I, the observed chemoselectivity towards ester hydrolysis, without amide reaction, broadens the information about the selectivity of the enzyme and its synthetic applications in the field of nucleosides.
Fil: Palacio, Cyntia M.. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología; Argentina
Fil: Sabaini, María Belén. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Iribarren, Adolfo Marcelo. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Investigaciones en Ingeniería Genética y Biología Molecular "Dr. Héctor N. Torres"; Argentina. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología; Argentina
Fil: Iglesias, Luis Emilio. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Subject
CHEMOSELECTIVITY
CANDIDA ANTARCTICA LIPASE B
ACYLASE I
NUCLEOBASE N-PROTECTION
OLIGONUCLEOTIDE BUILDING BLOCKS
Otras Ciencias Químicas
Ciencias Químicas
CIENCIAS NATURALES Y EXACTAS
Access level
Restricted access
License
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repository
CONICET Digital (CONICET)
Institution
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identifier
oai:ri.conicet.gov.ar:11336/24092