Premium
Nucleotides. Part LV . Synthesis and application of a novel linker for solid‐phase synthesis of modified oligonucleotides
Author(s) -
Waldvogel Siegfried R.,
Pfleiderer Wolfgang
Publication year - 1998
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.19980810106
Subject(s) - chemistry , linker , bifunctional , solid phase synthesis , guanosine , oligonucleotide , nucleotide , molecule , stereochemistry , combinatorial chemistry , protecting group , organic chemistry , biochemistry , catalysis , peptide , dna , alkyl , computer science , gene , operating system
Various bifunctional amino‐protecting groups such as the phthaloyl, succinyl, and glutaryl group were investigated as potential linker molecules for attachment to solid‐support materials. Pentane‐1,3,5‐tricarboxylic acid 1,3‐anhydride ( 16 ) offered the best properties and reacted with the amino groups of differently sugar‐protected adenosine (see 20 and 22 ), cytidine (see 29 ), and guanosine derivatives (see 32 ) to the corresponding 2‐(2‐carboxyethyl)glutaryl derivatives 23 , 24 , 30 , and 33 . The usefulness of the new linker‐type molecules was demonstrated by the solid‐support synthesis of the potentially antivirally active 3′‐deoxyadenylyl‐(2′–5′)‐2′‐adenylic acid 2′‐{2‐[(adenin‐9‐yl)methoxy]ethyl} ester ( 38 ) starting from the 2′‐end with N 6 , N 6 ‐[2‐(2‐carboxyethyl)glutaryl]‐9‐{{2‐[(4,4′‐dimethoxytrityl)ethoxy]methyl}adenine ( 12 ).