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

Paper ID Volume ID Publish Year Pages File Format Full-Text
23525 43446 2013 3 PDF Available
Title
An efficient and mild access to N-acetyl protected purine nucleosides based on a chemoselective enzymatic hydrolysis
Abstract

•N-Monoacetylated purine nucleosides were chemoselectively obtained in 88–100%.•Best results afforded by Candida antarctica lipase B and acylase I (Asp. melleus).•Information about applications of acylase I and its selectivity is broadened.

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.

Keywords
Chemoselectivity; Candida antarctica lipase B; Acylase I; Nucleobase N-protection; Oligonucleotide building blocks
First Page Preview
An efficient and mild access to N-acetyl protected purine nucleosides based on a chemoselective enzymatic hydrolysis
Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Biotechnology - Volume 165, Issue 2, 20 May 2013, Pages 99–101
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering