412031-52-8Relevant academic research and scientific papers
Immunomodulating glycosphingolipids: An efficient synthesis of a 2′-deoxy-α-galactosyl-GSL
Costantino, Valeria,Fattorusso, Ernesto,Imperatore, Concetta,Mangoni, Alfonso
, p. 369 - 375 (2007/10/03)
A new and efficient approach to the total synthesis of 2′-deoxy-α-galactosyl glycosphingolipids was accomplished. Commercially available 3,4,6-tri-O-acetylgalactal was used as the chiral starting material for both the sugar and phytosphingosine building blocks required for the synthesis of 1-O-(2-deoxy-α-D-galactopyranosyl)-2-docosanoylamino-1,3, 4-octadecanetriol. The key step of the synthetic strategy was the stereoselective α-glycosidation of the azido precursor of sphingosine.
Pentopyranosyl oligonucleotide systems. Part 11: Systems with shortened backbones: (D)-β-ribopyranosyl-(4′→3′)- and (L)-α-lyxopyranosyl-(4′→3′)-oligonucleotides
Wippo, Harald,Reck, Folkert,Kudick, Rene,Ramaseshan, Mahesh,Ceulemans, Griet,Bolli, Martin,Krishnamurthy, Ramanarayanan,Eschenmoser, Albert
, p. 2411 - 2428 (2007/10/03)
Th (L)-α-lyxopyranosyl-(4'→3')-oligonucleotide system - a member of a pentopyranosyl oligonucleotide family containing a shortened backbone - is capable of cooperative bas -pairing and of cross-pairing with DNA and RNA. In contrast, corresponding (D)-β-ribopyransoyl-(4'→3' )-oligonucleotides do not show base-pairing under similar conditions. We conclude that oligonucleotide systems can violate the 'six-bonds-per-backbone-unit' rule by having five bonds instead, if their vicinally bound phosphodiester bridges can assume an antiperiplanar conformation. An additional structural feature that seems relevant to the cross-pairing capability of the (L)-α-lyxopyranosyl-(4'→3')-oligonucleotide system is its (small) backbone/ basepair axes inclination. An inclination which is similar to that in B-DNA seems to b a prerequisite for an oligonucleotide system's capability to cross-pair with DNA. Copyright
