Ethynyl Side Chain Hydration during Synthesis and Workup of ``Clickable'' Oligonucleotides: Bypassing Acetyl Group Formation by Triisopropylsilyl Protection

Autor(en): Ingale, Sachin A.
Mei, Hui
Leonard, Peter
Seela, Frank
Stichwörter: AZIDE; Chemistry; Chemistry, Organic; CYCLOADDITION; DNA-SYNTHESIS; DUPLEX STABILITY; FUNCTIONALIZATION; IN-VIVO; MAJOR GROOVE; NUCLEIC-ACIDS; NUCLEOSIDES; TERMINAL ALKYNES
Erscheinungsdatum: 2013
Herausgeber: AMER CHEMICAL SOC
Journal: JOURNAL OF ORGANIC CHEMISTRY
Volumen: 78
Ausgabe: 22
Startseite: 11271
Seitenende: 11282
Zusammenfassung: 
Clickable oligonucleotides with ethynyl residues in the 5-position of pyrimidines ((eth)dC and (eth)dU) or the 7-position of 7-deazaguanine ((eth)c(7)G(d)) are hydrated during solid-phase oligonucleotide synthesis and workup conditions. The side products were identified as acetyl derivatives by MALDI-TOF mass spectra of oligonucleotides and by detection of modified nucleosides after enzymatic phosphodiester hydrolysis. Ethynyl -> acetyl group conversion was also studied on ethynylated nucleosides under acidic and basic conditions. It could be shown that side chain conversion depends on the nucleobase structure. Triisopropylsilyl residues were introduced to protect ethynyl residues from hydration. Pure, acetyl group free oligonucleotides were isolated after desilylation in all cases.
ISSN: 00223263
DOI: 10.1021/jo401780u

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