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Synthesis of Caged Nucleosides with Photoremovable Protecting Groups Linked to Intramolecular Antennae
Author(s) -
Smirnova Joulia,
Wöll Dominik,
Pfleiderer Wolfgang,
Steiner Ulrich E.
Publication year - 2005
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200590067
Subject(s) - chemistry , intramolecular force , ring (chemistry) , protecting group , thymidine , stereochemistry , covalent bond , group (periodic table) , dna , combinatorial chemistry , organic chemistry , biochemistry , alkyl
Based on the [2‐(2‐nitrophenyl)propoxy]carbonyl (nppoc) group, six new photolabile protecting groups ( 2, 8, 9b, 16b, 25b , and 26 ), each covalently linked to a 9 H ‐thioxanthen‐9‐one (Tx) unit functioning as an intramolecular triplet sensitizer, were synthesized. Linkers were introduced between the Me group or the aromatic ring of nppoc and the 2‐position of Tx by means of classical organic synthesis combined with Pd catalyzed CC coupling reactions. The new photolabile protecting groups to be used in light‐directed synthesis of DNA chips were attached to the 5′‐O‐atom of thymidine via a carbonate linkage, giving rise to the caged nucleosides 7, 11, 13, 19, 20 , and 30 .