351060-20-3Relevant academic research and scientific papers
Synthesis and O-Glycosidic Linkage Conformational Analysis of 13C-Labeled Oligosaccharide Fragments of an Antifreeze Glycolipid
Zhang, Wenhui,Meredith, Reagan,Yoon, Mi-Kyung,Wang, Xiaocong,Woods, Robert J.,Carmichael, Ian,Serianni, Anthony S.
, p. 1706 - 1724 (2019/02/14)
NMR studies of two 13C-labeled disaccharides and a tetrasaccharide were undertaken that comprise the backbone of a novel thermal hysteresis glycolipid containing a linear glycan sequence of alternating [βXylp-(1→4)-βManp-(1→4)]n dimers. Experimental trans-glycoside NMR J-couplings, parameterized equations obtained from density functional theory (DFT) calculations, and an in-house circular statistics package (MA'AT) were used to derive conformational models of linkage torsion angles φ and ψ in solution, which were compared to those obtained from molecular dynamics simulations. Modeling using different probability distribution functions showed that MA'AT models of φ in βMan(1→4)βXyl and βXyl(1→4)βMan linkages are very similar in the disaccharide building blocks, whereas MA'AT models of ψ differ. This pattern is conserved in the tetrasaccharide, showing that linkage context does not influence linkage geometry in this linear system. Good agreement was observed between the MA'AT and MD models of ψ with respect to mean values and circular standard deviations. Significant differences were observed for φ, indicating that revision of the force-field employed by GLYCAM is probably needed. Incorporation of the experimental models of φ and ψ into the backbone of an octasaccharide fragment leads to a helical amphipathic topography that may affect the thermal hysteresis properties of the glycolipid.
Direct chemical synthesis of the β-D-mannans: The β-(1→2) and β-(1→4) series
Crich, David,Banerjee, Abhisek,Yao, Qingjia
, p. 14930 - 14934 (2007/10/03)
The direct syntheses of β-(1→2)-mannooctaose and of β-(1→4)-mannohexaose are reported by means of 4,6-O-benzylidene- protected β-mannosyl donors. The synthesis of the (1→2)-mannan was achieved by means of the sulfoxide coupling protocol, whereas the (1→4)
Direct chemical synthesis of the β-mannans: Linear and block syntheses of the alternating β-(1→3)-β-(1→4)-mannan common to Rhodotorula glutinis, Rhodotorula mucilaginosa, and Leptospira biflexa
Crich, David,Li, Wenju,Li, Hongmei
, p. 15081 - 15086 (2007/10/03)
Two stereocontrolled syntheses of a methyl glycoside of an alternating β-(1→4)-β-(1→3)-mannohexaose, representative of the mannan from Rhodotorula glutinis, Rhodotorula mucilaginosa, and Leptospira biflexa, are described. Both syntheses employ a combinati
A new stereocontrolled access to β-D-mannopyranosides and 2-acetamido-2-deoxy-β-D-mannopyranosides starting from β-D-galactopyranosides
Attolino, Emanuele,Catelani, Giorgio,D'Andrea, Felicia
, p. 8815 - 8818 (2007/10/03)
A new stereocontrolled synthesis of β-D-mannopyranosides was defined relying on a high yielding sequence based on the following three key steps: (a) a stereospecific inversion at C-2 of β-D-galactopyranosides by an oxidation-reduction procedure; (b) a regiocontrolled formation of 4-deoxy-β-D-threo-hex-3-enopyranosides; (c) a regio- and stereocontrolled hydroboration-oxidation of the above enol ethers. The flexibility of this new method was demonstrated by its extension to the synthesis of 2-acetamido-2-deoxy-β-D-mannopyranosides and of an orthogonally protected β-D-mannopyranoside scaffold and, finally, by the transformation of lactose into the two biologically relevant disaccharides with primary structure β-D-Manp-(1→4)-D-Glc and β-D-ManNAcp-(1→4)-D-Glc.
