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Nucleotide, XVIII . Synthese und Eigenschaften von ( tert ‐Butyldimethylsilyl)guanosinen, Guanosin‐3′‐phosphotriestern und Guanosin‐haltigen Oligoncleotiden
Author(s) -
Flockerzi Dieter,
Schlosser Wilhelm,
Pfleiderer Wolfgang
Publication year - 1983
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.19830660718
Subject(s) - chemistry , guanosine , nucleotide , phosphodiester bond , stereochemistry , silylation , nmr spectra database , oligonucleotide , nucleic acid , organic chemistry , dna , catalysis , biochemistry , rna , physics , astronomy , spectral line , gene
Nucleotides, XVIII. Synthesis and Properties of ( tert ‐Butyldimethylsilyl)guanosines, Guanosine‐3′‐Phosphotriesters and Guanosine‐containing Oligonucleotides Silylation of N 2 ‐benzoyl‐ (1) and N 2 ‐isobutyrylguanosin (2) by tert ‐butyldimethylsilyl chloride led to the various mono‐, di‐ and tri‐ O ‐ tert ‐butyldimethylsilyl derivatives 3–15 . The synthesis of 2′‐ (24–31) and 3′‐phosphotriesters ( 16–23 and 32 ) could be achieved by phosphorylations of partially protected guanosines. The guanosine‐3′‐phosphodiester 33 and the 5′‐OH‐guanosine‐3′‐phosphotriester 34 are used in condensation reactions as 5′‐ and 3′‐terminal components, respectively, to form dinucleoside mono‐ ( 39 and 40 ) and diphosphates (41–48) in relatively good yields. The various products were characterized by elemental analyses, 1 H‐, 13 C‐, and 31 P‐NMR spectra as well as UV and CD spectra.