124290-99-9Relevant articles and documents
Selective cross-linking to the adenine of the TA interrupting site within the triple helix
Nagatsugi, Fumi,Matsuyama, Yoshihisa,Maeda, Minoru,Sasaki, Shigeki
, p. 487 - 489 (2002)
The triplex-forming oligonucleotide incorporating the new nucleoside derivative (2) that connects the 2-amino-6-vinylpurine moiety to the 2-deoxyribose unit with an ethyl spacer has exhibited highly selective cross-linking reaction to the adenine of the TA interrupting site within the triple helix.
Stereocontrolled Synthesis of a Possible Stereoisomer of Laurenidificin and a Formal Total Synthesis of (+)-Aplysiallene Featuring a Stereospecific Ring Contraction
Kobayashi, Shoji,Yokoi, Taiki,Inoue, Tomoharu,Hori, Yutaka,Saka, Tomoaki,Shimomura, Taiki,Masuyama, Araki
, p. 1484 - 1498 (2016/03/01)
We report a highly stereocontrolled total synthesis of one of the possible stereoisomers of laurenidificin. Highlights of the synthesis include the formation of the 2,6-dioxabicyclo[3.3.0]octane framework by a stereospecific bromolactonization-α-bromination-ring contraction sequence, followed by a stereoselective propargylation, an insertion of the Z-enyne side chain by a hydroindation/cross coupling reaction, and ethylation at C13 with an organocuprate reagent. While the synthetic compound was not identical to the natural product, the absolute stereochemistry of the natural product was proposed on the basis of NMR analyses. Moreover, a formal total synthesis of (+)-aplysiallene was achieved by extending the ring contraction strategy. (Chemical Equation Presented).
Selective reaction to a flipping cytidine of the duplex DNA mediated by triple helix formation
Nagatsugi, Fumi,Usui, Daisaku,Kawasaki, Takeshi,Maeda, Minoru,Sasaki, Shigeki
, p. 343 - 345 (2007/10/03)
A new nucleoside derivative (2) with a butyl spacer between the sugar part and the 2-amino-6-vinylpurine motif has been synthesized. The triplex-forming oligodeoxynucleotide incorporating 2 has achieved strand- and cytidine-selective cross-linking reaction to the G-C target site mediated by triple helix formation. It has been suggested that 2 reacts with a flipping cytidine at the target site.
A shortcut and stereoselective synthesis of 1-β-alkyl-2-deoxy-D-ribose derivatives via Wittig-Horner-Emmons reaction
Matsuura, Naoko,Yashiki, Yoshitaka,Nakashima, Shouji,Maeda, Minoru,Sasaki, Shigeki
, p. 975 - 978 (2007/10/03)
A shortcut and stereoselective synthesis of 1-β-alkyl-2-deoxy-D-ribose derivatives has been achieved via Wittig-Horner-Emmons reaction followed by intramolecular 1,4-addition. After the systematic investigation of the effects of the base and the solvent,
Synthesis of (2-deoxy-α- and -β-D-erythro-pentofuranosyl)(thymin-1-yl)alkanes and their incorporation into oligodeoxyribonucleotides. Effect of nucleobase-sugar linker flexibility on the formation of DNA-DNA and DNA-RNA hybrids
Boal, Jila H.,Wilk, Andrzej,Scremin, Carlo L.,Gray, Glenn N.,Phillips, Lawrence R.,Beaucage, Serge L.
, p. 8617 - 8626 (2007/10/03)
On the basis of modeling studies, the (2-deoxy-α- and β-D-erythro-pentofuranosyl) (thymin-1-yl) alkanes 1a,b and 2a,b were selected as potential conformational probes for altDNA oligonucleotides. A straightforward approach to the synthesis of 1a,b and 2a,b from commercial 2-deoxy-D-ribose (3) and 1-O-methyl-2-deoxy-3,5-di-0-p-toluoyl-D-erythro-pentofuranose (13), respectively, was developed. These nucleoside analogues were converted to the phosphoramidite derivatives 27a,b-30a,b and incorporated into oligonucleotide 31 at predetermined sites and defined internucleotidic motifs. The insertion of 1a,b according to either a (3′ → 5′)- or a (3′ → 3′)-internucleotidic polarity produced oligonucleotides exhibiting a slightly higher affinity for their complementary unmodified DNA sequence than for the corresponding RNA sequence (Table 3). Conversely, the incorporation of 2a into 31 according to a (3′ → 3′)-orientation generated, for the first time, an altDNA oligonucleotide displaying a greater affinity for its complementary unmodified RNA sequence (ΔTm = 6°C) than for the corresponding DNA sequence (ΔTm = 10°C). This hybrid was, however, thermodynamically less stable than the duplex having unmodified α-2′-deoxythymidine similarly incorporated into 31 (ΔΔTm = 3°C).
1-(2-Deoxy-α- and β-D-erythro-pentofuranosyl)-2-(thymin-1-yl)ethane Derivatives as Conformational Probes for altDNA Oligonucleotides
Scremin, Carlo L.,Boal, Jila H.,Wilk, Andrzej,Phillips, Lawrence R.,Zhou, Liang,Beaucage, Serge L.
, p. 8953 - 8956 (2007/10/02)
The novel deoxyribonucleoside analogues 1a,b have been synthesized in a straightforward manner from 2-deoxy-D-ribose.These modified nucleosides have also been converted to the phosphoramidite derivatives 13a,b and 14a,b for potential incorporation into ol
