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Nucleoside und nucleotide. Teil 4. Festphasensynthese von Oligonucleotiden an einem unlöslichen, makroporösen Träger
Author(s) -
Glaser Remo,
Séquin Urs,
Tamm Christoph
Publication year - 1973
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.19730560212
Subject(s) - chemistry , nucleoside , polymer , thymidine , phosphate , cleavage (geology) , polystyrene , nucleic acid , nucleotide , chloride , phosphoryl chloride , stereochemistry , dna , polymer chemistry , medicinal chemistry , organic chemistry , biochemistry , geotechnical engineering , fracture (geology) , engineering , gene
Insoluble, macroreticular, highly cross‐linked polystyrene with projecting mono‐methoxytrityl chloride groups 4 was prepared and condensed with thymidine (T D ) as well as with 1‐(2′‐deoxy‐ß‐D‐ribofuranosyl)‐2(1 H )‐pyridone ( II d ) to give the polymers 5 and 6 respectively, containing approximately 465 μmoles resp. 650 μmoles of bound nucleoside per gram of polymer. A standard procedure for removal of the products from the support is described. Condensation of the polymer‐bound nucleosides 5 and 6 , respectively, with 3′‐O‐acetyl‐thymidine‐5′‐phosphate ( 7 ) in the presence of mesitylenesulfonyl chloride (MS) and subsequent removal from the polymer yielded the dinucleoside phosphates T d ‐T d ( 9 ) and II d ‐T d ( 11 ) respectively. Condensation of the polymer 8 with 3′‐O‐acetyl‐thymidine‐5′‐phosphate ( 7 ) in the presence of MS and cleavage of the polymer linkage gave the trithymidine diphosphate (T d ‐T d ‐T d ) ( 13 ). Phosphorylation of the polymer‐bound nucleosides 5 and 6 with ß‐cyanoethyl phosphate in presence of MS took place in 3′‐position. Similarly the polymer‐bound dinucleoside phosphates 8 and 10 gave 16 and 17 respectively.