Cross-Linked DNA: Site-Selective ``Click'' Ligation in Duplexes with Bis-Azides and Stability Changes Caused by Internal Cross-Links

Autor(en): Xiong, Hai
Seela, Frank
Stichwörter: 1,3-DIPOLAR CYCLOADDITION; Biochemical Research Methods; Biochemistry & Molecular Biology; BUILDING-BLOCKS; Chemistry; Chemistry, Multidisciplinary; Chemistry, Organic; FUNCTIONALIZATION; NUCLEOSIDES; NUCLEOTIDE; OLIGONUCLEOTIDES; SIDE-CHAINS
Erscheinungsdatum: 2012
Herausgeber: AMER CHEMICAL SOC
Journal: BIOCONJUGATE CHEMISTRY
Volumen: 23
Ausgabe: 6
Startseite: 1230
Seitenende: 1243
Zusammenfassung: 
Heterodimeric interstrand cross-linked DNA was constructed by the ``bis-click'' reaction carried out on preformed oligonucleotide duplexes with the bis-azide 1. For this, alkynylated 8-aza-7-deazapurine or corresponding 5-substituted pyrimidine nucleosides were synthesized. Cross-linking resulted in chemoselective formation of heterodimeric duplexes while homodimers were suppressed. For product identification, heterodimeric DNA was prepared by the ``stepwise click'' reaction, while noncomplementary homodimers were accessible by ``bis-click'' chemistry, unequivocally. Studies on duplex melting of complementary cross-linked duplexes (heterodimers) revealed significantly increased T-m values compared to the non-cross-linked congeners. The stability of this cross-linked DNA depends on the linker length and the site of modification. Cross-linked homodimers hybridized with single-stranded complementary oligonucleotides show much lower stability.
ISSN: 10431802
DOI: 10.1021/bc300074k

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