66537-92-6Relevant articles and documents
Reactivity–Stereoselectivity Mapping for the Assembly of Mycobacterium marinum Lipooligosaccharides
Hansen, Thomas,Ofman, Tim P.,Vlaming, Joey G. C.,Gagarinov, Ivan A.,van Beek, Jessey,Goté, Tessa A.,Tichem, Jacoba M.,Ruijgrok, Gijs,Overkleeft, Herman S.,Filippov, Dmitri V.,van der Marel, Gijsbert A.,Codée, Jeroen D. C.
supporting information, p. 937 - 945 (2020/12/09)
The assembly of complex bacterial glycans presenting rare structural motifs and cis-glycosidic linkages is significantly obstructed by the lack of knowledge of the reactivity of the constituting building blocks and the stereoselectivity of the reactions i
Hybridisation potential of 1′,3′-Di-O-methylaltropyranoside nucleic acids
Venkatesham, Akkaladevi,Kachare, Dhuldeo,Schepers, Guy,Rozenski, Jef,Froeyen, Mathy,Van Aerschot, Arthur
, p. 4020 - 4041 (2015/05/06)
In further study of our series of six-membered ring-containing nucleic acids, different 1′,3′-di-O-methyl altropyranoside nucleoside analogs (DMANA) were synthesized comprising all four base moieties, adenine, cytosine, uracil and guanine. Following assembly into oligonucleotides (ONs), their affinity for natural oligonucleotides was evaluated by thermal denaturation of the respective duplexes. Data were compared with results obtained previously for both anhydrohexitol (HNAs) and 3′-O-methylated altrohexitol modified ONs (MANAs). We hereby demonstrate that ONs modified with DMANA monomers, unlike some of our previously described analogues with constrained 6-membered hexitol rings, did not improve thermodynamic stability of dsRNA complexes, most probably in view of an energetic penalty when forced in the required 1C4 pairing conformation. Overall, a single incorporation was more or less tolerated or even positive for the adenine congener, but incorporation of a second modification afforded a slight destabilization (except for A), while a fully modified sequence displayed a thermal stability of -0.3°C per modification. The selectivity of pairing remained very high, and the new modification upon incorporation into a DNA strand, strongly destabilized the corresponding DNA duplexes. Unfortunately, this new modification does not bring any advantage to be further evaluated for antisense or siRNA applications.
α- and β-Lipomycin: Total syntheses by sequential stille couplings and assignment of the absolute configuration of all stereogenic centers
Hofferberth, Max L.,Brückner, Reinhard
, p. 7328 - 7334 (2014/07/21)
40 years ago spectroscopy, derivatization, and degradation revealed the structures of α-lipomycin and its aglycon β-lipomycin except for the configurations of their side-chain stereocenters. We synthesized all relevant β-lipomycin candidates: the (12R,13S