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Fmoc‐Protected Altritol Phosphoramidite Building Blocks and Their Application in the Synthesis of Altritol Nucleic Acids (ANAs)
Author(s) -
Abramov Mikhail,
Schepers Guy,
Van Aerschot Arthur,
Herdewijn Piet
Publication year - 2007
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/ejoc.200600868
Subject(s) - phosphoramidite , chemistry , oligonucleotide , nucleic acid , thymine , combinatorial chemistry , uracil , oligonucleotide synthesis , guanine , nucleoside , pseudouridine , cytosine , protecting group , rna , stereochemistry , nucleotide , organic chemistry , biochemistry , transfer rna , dna , alkyl , gene
Fmoc‐protected altritol nucleoside phosphoramidite building blocks with adenine, guanine, thymine, uracil, cytosine and 5‐methylcytosine as bases have been synthesized. These building blocks were used for the synthesis of altritol nucleic acid (ANA) and chimeric ANA‐RNA oligonucleotides. Whilst the yields of oligonucleotides were lower than those obtained with 3′‐ O ‐benzoyl‐protected altritol building blocks, the excellent compatibility with Pac‐RNA chemistry for the synthesis of chimeric oligonucleotides makes Fmoc a valuable protecting group for the secondary alcohol functions of the sugar moieties of nucleosides for oligonucleotide synthesis.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)