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

Journal of Biotechnology

Volumn 165, Issue 2, 2013, Pages 99-101

  Palacio, Cyntia M ^a   Sabaini, María B ^a   Iribarren, Adolfo M ^a,b   Iglesias, Luis E ^a  

^a UNIVERSIDAD NACIONAL DE QUILMES   (Argentina)

^b INSTITUTO DE INVESTIGACIONES EN INGENIERÍA GENÉTICA Y BIOLOGÍA MOLECULAR   (Argentina)

Author keywords

Acylase I; Candida antarctica lipase B; Chemoselectivity; Nucleobase N protection; Oligonucleotide building blocks

Indexed keywords

ACYLASE I; BUILDING BLOCKES; CANDIDA ANTARCTICA LIPASE B; 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;

ASPERGILLUS MELLEUS; CANDIDA ANTARCTICA;

EID: 84876737055     PISSN: 01681656     EISSN: 18734863     Source Type: Journal    
DOI: 10.1016/j.jbiotec.2013.03.004     Document Type: Article

References (19)

1. Beaucage S.L., Reese C.B. Recent advances in the chemical synthesis of RNA. Current Protocols in Nucleic Acid Chemistry 2009, 38:2.16.1-2.16.31.
2. Blat V., Ugarkar B.G., Sayeed V.A., Grimm K., Kosora N., Domenico P.A., Stocker E. A simple and convenient method for the selective N-acylations of cytosine nucleosides. Nucleosides and Nucleotides 1989, 8:179-183.
3. Bornscheuer U., Kazlauskas R. Hydrolases in Organic Chemistry 2006, 122. Wiley-VCH, Weinheim. 2nd ed.
4. Chenault H.K., Dahmer J., Whitesides G.M. Kinetic resolution of unnatural and rarely occurring amino acids: enantioselective hydrolysis of N-acyl amino acids catalysed by acylase I. Journal of the American Chemical Society 1989, 111:6354-6364.
5. Díaz-Rodríguez A., Fernández S., Sanghvi Y.S., Ferrero M., Gotor V. Novel chemoenzymatic protocol for the synthesis of 3'-O-dimethoxytrityl-2'-deoxynucleoside derivatives as building blocks for oligonucleotide synthesis. Organic Process Research and Development 2006, 10:581-587.
6. Faber K. Biotransformations in Organic Chemistry 2004, Wiley-VCH, Mannheim. 5th ed.
7. Ferrero M., Gotor V. Biocatalytic selective modifications of conventional nucleosides, carbocyclic nucleosides and C-nucleosides. Chemical Reviews 2000, 100:4319-4347.
8. Ferrero M., Gotor V. Chemoenzymatic transformations in nucleoside chemistry. Monatshefte fur Chemie 2000, 131:585-616.
9. Jones R.A. Preparation of protected deoxyribonucleosides. Oligonucleotide Synthesis: A Practical Approach 1985, 23-34. IRL Press, Oxford. M.J. Gait (Ed.).
10. Kadereit D., Waldmann H. Enzymatic protective group techniques. Chemical Reviews 2001, 101:3367-3396.
11. Li N., Smith T.J., Zong M.H. Biocatalytic transformations of nucleoside derivatives. Biotechnology Advances 2010, 28:348-366.
12. Liljeblad A., Ajsela R., Kanerva L.T. Use of enantio-chemo-, and regioselectivity of acylase I. Resolution of polycarboxylic acid esters. Tetrahedron: Asymmetry 2001, 12:2059-2066.
13. Liljeblad A., Kanerva L.T. Enzymatic methods for the preparation of enantiopure malic and aspartic acid derivatives in organic solvents. Tetrahedron: Asymmetry 1999, 10:4405-4415.
14. Liljeblad A., Kanerva L.T. Biocatalysis as a profound tool in the preparation of highly enantiopure β-amino acids. Tetrahedron: Asymmetry 2006, 62:5831-5854.
15. Liljeblad A., Lindborg J., Kanerva L.T. Acylase I in the alcoholysis of α-substituted dicarboxylic acid esters and derivatives: enantio- and regioselectivity. Tetrahedron: Asymmetry 2000, 11:3957-3966.
16. Pitsch S., Weiss P.A., Jenny L., Stutz A., Wu X. Reliable chemical synthesis of oligoribonucleotides (RNA) with 2'-O-[(triisopropylsilyl)oxy] methyl(2'-O-tom)-protected phosphoramidites. Helvetica Chimica Acta 2001, 84:3773-3795.
17. Ac derivatives. Nucleosides and Nucleotides 1997, 16:179-183.
18. Simons C., Van Leeuwen J.G.E., Stemmer R., Arends I.W.C.E., Maschmeyer T., Sheldon R.A., Hanefeld U. Enzyme-catalysed deprotection of N-acetyl and N-formyl amino acids. Journal of Molecular Catalysis B: Enzymatic 2008, 54:67-71.
19. Torres-Gavilán A., Castillo E., López-Munguía A. The amidase activity of Candida antarctica B lipase is dependent on specific structural features of the substrates. Journal of Molecular Catalysis B: Enzymatic 2006, 41:136-140.