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Synthesis of 3′(2′)‐ O ‐Lysophosphatidylnucleosides − a Further Application of a Chemoenzymatic Strategy
Author(s) -
Chillemi Rosa,
Aleo Danilo,
Granata Giuseppe,
Sciuto Sebastiano
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200211)2002:21<3622::aid-ejoc3622>3.0.co;2-4
Subject(s) - chemistry , moiety , nucleoside , nucleic acid , lipase , acylation , methanol , stereochemistry , regioselectivity , organic chemistry , catalysis , enzyme , biochemistry
Mono[(2 R )‐2,3‐dihydropropyl] esters of the four 3′‐nucleotides of DNA, prepared from protected nucleoside phosphoramidites and [(4 S )‐2,2‐dimethyl‐1,3‐dioxolan‐4‐yl]methanol, were regioselectively acylated at the C‐1 hydroxyl of the glycerol moiety by a lipase‐catalyzed transacylation with activated palmitic acid ester in organic solvent, giving the relevant 3′‐ O ‐lysophosphatidyl‐2′‐deoxynucleosides. The synthesis was also adapted for the preparation of 3′‐ O ‐lysophosphatidyl derivatives of 5′‐deoxy‐5‐fluorouridine and 5′‐deoxy‐5′‐(methylthio)adenosine, with the 2′‐ O ‐isomer of the latter compound also being prepared. The enhanced ability of lysophosphatidyl compounds to interact with lipid monolayers was also tested in comparison with that of the relevant free nucleosides. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)