245366-55-6

Upstream product

• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 230631-22-8 (1S,3R,4R,7R)-7-Hydroxy-1-hydroxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane 
• 410076-93-6 3-O-benzyl-1,2-di-O-acetyl-5-O-(methylsulfonyl)-4-C-(methylsulfonyloxymethyl)-α,β-L-threo-pentofuranose 
• 861230-75-3 (1S,3R,4R,7R)-7-benzyloxy-1-(hydroxymethyl)-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane 
• 601512-74-7 1-[2-O-acetyl-3-O-benzyl-5-O-(methylsulfonyl)-4-C-(methylsulfonyloxymethyl)-α-L-threo-pentofuranosyl]thymine 

Relevant academic research and scientific papers

LNA stereoisomers: Xylo-LNA (β-D-xylo configured locked nucleic acid) and α-L-LNA (α-L-ribo configured locked nucleic acid)

Synthesis of xylo-LNA containing one 2′-O,4′-C-methyleneβ-D-xylofuranosyl thymine nucleotide monomer and α-LLNAs containing one or four 2′-O,4′-C-methyIene-α-Lribofuranosyl thymine nucleotide monomer(s) has been accomplished using phosphoramidite chemistr

XYLO-LNA ANALOGUES

A bicyclic nucleoside derivative, wherein an intranucleoside ring locks the ring conformation of the nucleoside, is termed an LNA - a Locked Nucleic Acid. LNAs of the xylo-configuration, considered useful as therapeutic agents, diagno

XNA ?(xylo nucleic acid): A summary and new derivatives

Fully modified homopyrimidine 2′-deoxy-xylo nucleic acid (dXNA) form triple helixes with complementary DNA/RNA with thermal stabilities comparable to those of the corresponding DNA:DNA and DNA:RNA duplexes. However, a single or few insertions of dXNA monomers in a DNA strand significantly lower duplex stabilities. The dXNA monomers are known to adopt predominantly an N-type furanose conformation in solution. With a desire to increase the binding affinity, seven sugar-modified XNA monomers (H, F, N, M, K, P and Q) have been synthesised and their effect on hybridization towards DNA and RNA complements studied. The introduction of 2′-fluoro and 2′-hydroxy substituents was expected to induce conformational restriction towards C3′-endo-type furanose conformation of monomer F derived from 1-(2′-deoxy-2′-fluoro-β-D-xylofuranosyl)thymine and monomer H derived from 1-(β-D-xylofuranosyl)thymine. The presence of functionalites facing the minor groove as in 1-(2′-amino-2′-deoxy-2′-N, 4′-C-methylene-β-D-xylofuranosyl)thymine (monomer N), 1-[4-C-(N-methylpiperazinyl)methyl-β-D-xylofuranosyl]thymine (monomer P), 1-(4-C-piperazinylmethyl-β-D-xylofuranosyl)thymine (monomer Q), 1-(4-C-hydroxymethyl-β-D-xylofuranosyl)thymine (monomer M) and 9-(4-C-hydroxymethyl-β-D-xylofuranosyl)adenine (monomer K) was studied, with monomer N being locked in an N-type furanose conformation. Besides, an efficient synthesis of known xylo-LNA phosphoramidite 19, required for the incorporation of 1-(2′-O,4′-C-methylene-β-D-xylofuranosyl)thymine (monomer L) is described. For comparison, hydridization data of various XNAs reported in the literature are included in the discussion section. The thermal denaturation studies show that XNAs containing conformationally locked monomers (N and L) display improved binding affinity, and that partially modified DNA/XNA chimera, or fully modified XNA display preferential hybridization towards RNA complements. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.

Xylo-LNA analogues

Based on the above and on the remarkable properties of the 2′-O,4′-C-methylene bridged LNA monomers it was decided to synthesise oligonucleotides comprising one or more 2′-O,′-C-methylene-β-D-xylofuranosyl nucleotide monomer(s) as the first stereoisomer o