Parallel-stranded DNA: Enhancing duplex stability by the `G-clamp' and a pyrrolo-dC derivative

Autor(en): Ming, Xin
Ding, Ping
Leonard, Peter
Budow, Simone
Seela, Frank
Stichwörter: ANTIPARALLEL CHAIN ORIENTATION; BASE-PAIRS; Chemistry; Chemistry, Organic; CRYSTAL-STRUCTURE; FLUORESCENCE; GUANINE; HYBRIDIZATION PROPERTIES; ISOGUANINE-CYTOSINE; NUCLEIC-ACIDS; OLIGONUCLEOTIDE DUPLEXES; TRIPLEX DNA
Erscheinungsdatum: 2012
Herausgeber: ROYAL SOC CHEMISTRY
Journal: ORGANIC & BIOMOLECULAR CHEMISTRY
Volumen: 10
Ausgabe: 9
Startseite: 1861
Seitenende: 1869
Zusammenfassung: 
The new pyrrolo-dC derivative 4 tethered with an alkylamino side chain via a triazole linker was synthesized. Oligonucleotides containing the G-clamp 3 or the pyrrolo-dC derivative 4 were prepared. Oligonucleotide synthesis and deprotection under standard conditions led to unwanted side product formation. The side product was identified as an acrylonitrile adduct of the aminoalkyl side chain. Changing the synthesis and work-up conditions to fast-deprotection chemistry and performing beta-elimination of the cyanoethyl group on the solid support yielded pure oligonucleotides. Oligonucleotide duplexes with parallel chain orientation were constructed incorporating dA.dT and isoG(d).dCbase pairs. Replacement of dC-residues by the G-clamp 3 led to extraordinarily stable duplexes (Delta T-m = 11 degrees C for two incorporations) in ps DNA, while the pyrrolo-dC derivative 4 behaved like dC. Surprisingly, the G-clamp 3 forms an even more stable base pair with 2'-deoxyisoguanosine in DNA with parallel chain orientation than with 2'-deoxyguanosine in aps DNA.
ISSN: 14770520
DOI: 10.1039/c2ob06606h

Show full item record

Page view(s)

3
Last Week
0
Last month
0
checked on Mar 1, 2024

Google ScholarTM

Check

Altmetric