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Fast and Reliable Automated Synthesis of RNA and Partially 2′‐ O ‐ Protected Precursors (`Caged RNA') Based on Two Novel, Orthogonal 2′‐ O ‐Protecting Groups, Preliminary Communication
Author(s) -
Pitsch Stefan,
Weiss Patrick A.,
Wu Xiaolin,
Ackermann Damian,
Honegger Thomas
Publication year - 1999
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/(sici)1522-2675(19991006)82:10<1753::aid-hlca1753>3.0.co;2-y
Subject(s) - chemistry , ribozyme , protecting group , rna , cleavage (geology) , stereochemistry , group (periodic table) , alkoxy group , substrate (aquarium) , biochemistry , organic chemistry , alkyl , geotechnical engineering , fracture (geology) , engineering , gene , oceanography , geology
Two sets of RNA phosphoramidites, carrying the (fluoride‐labile) 2′‐ O ‐[(triisopropylsilyl)oxy]methyl (=tom) group and the (photolabile) [( R )‐1‐(2‐nitrophenyl)ethoxy]methyl (=( R )‐npeom) group, were prepared (see 1 – 4 and 5 – 8 , resp.). The two protecting groups were completely orthogonal to each other. Three ribozyme‐substrate constructs, protected each by a ( R )‐npeom group, were synthesized; on photolysis, efficient cleavage of this remaining protecting group occurred ( Scheme 3 ). It could be demonstrated that the presence of one ( R )‐npeom group within a RNA strand has only a minor influence on the pairing properties of corresponding duplexes.