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

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...

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Detalles Bibliográficos
Autores principales: Palacio, C.M., Sabaini, M.B., Iribarren, A.M., Iglesias, L.E.
Formato: JOUR
Materias:
Acylase I
Candida antarctica lipase B
Chemoselectivity
Nucleobase N-protection
Oligonucleotide building blocks
Building blockes
Chemo-selectivity
Nucleobases
Enzymatic hydrolysis
Isomers
Oligonucleotides
Biomolecules
aminoacylase
hydrolase
purine nucleoside
article
Aspergillus melleus
chemical reaction
chemoselective enzymatic hydrolysis
deacetylation
deprotection reaction
enzyme synthesis
hydrolysis
priority journal
quantitative analysis
synthesis
Amidohydrolases
Aspergillus
Fungal Proteins
Hydrolysis
Lipase
Purine Nucleosides
Candida antarctica
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_01681656_v165_n2_p99_Palacio
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
Descripción
Sumario: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. © 2013 Elsevier B.V.

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