Furanose ring conformations in a 1′-alkynyl C-nucleoside and the dinucleotide

Additive‐Free Enzymatic Phosphorylation and Ligation of Artificial Oligonucleotides with C‐Nucleosides at the Reaction Points

“…Moreover, the duplexes showed melting temperatures quite near to those of natural ones with the same sequence context. The 1′‐ethynyldeoxyribose component in the artificial DNA showed the S‐type puckering conformation as seen in natural B‐DNA, thus being partially responsible for the above similarities . In view of these characteristics, our artificial DNA is one of the most closely similar DNA‐like analogues reported so far…”

2-Aminopyridine as a Nucleobase Substitute for Adenine in DNA-like Architectures: Synthesis of Alkynyl C-Nucleotides and Their Hybridization Characteristics

“…We have reported DNA-like architectures made solely of alkynyl C -nucleotides possessing adenine ( A )-, thymine ( T )-, guanine ( G )-, and cytosine ( C )-like non-natural nucleobases at the acetylene termini. , The DNA-like oligomers exhibited right-handed double and triple helices in a sequence specific manner in water. The saccharide unit, ethynyl C -2-deoxy-β- d -ribofuranoside, was synthesized by our procedure and showed an S -type puckering conformation similar to the 2-deoxyribose residue in B-type DNA . This fact might be one of the reasons why our DNA-like oligomer closely resembles natural DNA in terms of structural and physicochemical aspects.…”

A firmly hybridizable, DNA-like architecture with DAD/ADA- and ADD/DAA-type nonnatural base pairs as an extracellular genetic candidate

“…We also revealed that the ethynylribose ring in the artificial DNA puckered into the S-type conformation as seen in B-type DNA, which would partly result in the above resemblance. 11 Our artificial DNA is one of the most faithfully mimicked DNA-like systems reported so far, in regard to having several features matching well with natural DNA. There is a great need for continuous chemical fine-tuning of artificial DNA to further imitate natural DNA.…”

“…The halogen-tethered nonnatural bases, D*-I, G*-I, and C*-I were synthesized from commercially available sources and attached to 4,4 0 -dimethoxytrityl-(DMTr-) protected ethynyl C-2-deoxy-b-Dribofuranoside 1 by a palladium-catalyzed coupling reaction to give nonnatural C-nucleosides in good to acceptable yields (Scheme S1 in the ESI †). [10][11][12] These C-nucleosides were then further protected on the base moieties and transformed into the corresponding phosphoroamidites. The three phosphoroamidites, together with the previously reported T*-phosphoroamidite, 10,11 were successfully subjected to conventional solid-phase automated DNA synthesis.…”

“…[10][11][12] These C-nucleosides were then further protected on the base moieties and transformed into the corresponding phosphoroamidites. The three phosphoroamidites, together with the previously reported T*-phosphoroamidite, 10,11 were successfully subjected to conventional solid-phase automated DNA synthesis. After having been cleaved from the solid support, the artificial oligomers were deprotected, purified by reverse-phase HPLC, and characterized by matrix-assisted laser desorption ionization timeof-flight (MALDI-TOF) mass spectrometry measurements (see the Measurements section and Fig.…”