Premium
Nucleotides. Part XLIII. Solid‐phase synthesis of oligoribonucleotides using the 2‐dansylethoxycarbonyl ( 2‐{[5‐(dimethylamino)naphthalen‐1‐yl]sulfonyl}ethoxycarbonyl; dnseoc) group for 5′‐hydroxy protection
Author(s) -
Bergmann Frank,
Pfleiderer Wolfgang
Publication year - 1994
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.19940770411
Subject(s) - chemistry , sulfonyl , solid phase synthesis , nucleotide , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , biochemistry , peptide , alkyl , gene
A new efficient method for solid‐phase synthesis of oligoribonucleotides via the phosphoramidite approach is described. The combination of the base‐labile 2‐dansylethoxycarbonyl (Dnseoc) group for 5′‐OH protection with the acid‐labile tetrahydro‐4‐methoxy‐2 H ‐pyran‐4‐yl (Thmp) group as 2′‐OH blocking group is orthogonal regarding cleavage reactions and fulfills the requirements of an automated synthesis in an excellent manner if the phosphoramidite function carries the N,N ‐diethyl‐ O ‐[2‐(4‐nitrophenyl)ethyl] substitution.