83441-64-9Relevant academic research and scientific papers
Automated glycan assembly of xyloglucan oligosaccharides
Dallabernardina, Pietro,Schuhmacher, Frank,Seeberger, Peter H.,Pfrengle, Fabian
supporting information, p. 309 - 313 (2015/12/30)
We report the automated glycan assembly of oligosaccharide fragments related to the hemicellulose xyloglucan (XG). Iterative addition of monosaccharide and disaccharide building blocks to a solid support provided seven cellulose and xyloglucan fragments i
Synthesis of QS-21-xylose: Establishment of the immunopotentiating activity of synthetic QS-21 adjuvant with a melanoma vaccine
Deng, Kai,Adams, Michelle M.,Damani, Payal,Livingston, Philip O.,Ragupathi, Govind,Gin, David Y.
supporting information; experimental part, p. 6395 - 6398 (2009/03/11)
(Chemical Equation Presented) A helping hand: The adjuvant QS-21-xylose (see structure; the xylose residue is shown in red) was obtained in pure form by chemical synthesis. When combined with its synthetic apiose isomer to furnish synthetic QS-21 (sQS-21), the saponin combination was shown to aid the production of antibodies in mice when injected with a melanoma vaccine. The preparation of sQS-21 provides access to pure, functional saponin adjuvants of defined composition.
Syntheses of pantolactone and pantothenic acid derivatives as potential lipid regulating agents
Oniciu, Daniela C.,Bell, Roel P. L.,McCosar, Bruce H.,Bisgaier, Charles L.,Dasseux, Jean-Louis H.,Verdijk, Dennis,Relou, Mike,Smith, Dennis,Regeling, Henk,Leemhuis, Frank M. C.,Ebbers, Eelco J.,Mueller, Ralf,Zhang, Lianhao,Pop, Emil,Cramer, Clay T.,Goetz, Brian,McKee, Andrew,Pape, Michael E.,Krause, Brian R.
, p. 365 - 391 (2007/10/03)
A series of pantolactone and pantothenic acid derivatives (1-10) were synthesized to be tested for their potential as lipid regulating agents that act as Coenzyme-A mimics. The syntheses were performed with moderate to high yields. Copyright Taylor & Fran
Glycosyl Imidates, 12. - Direct Synthesis of O-α- and O-β-Glycosyl Imidates
Schmidt, Richard R.,Michel, Josef,Roos, Michael
, p. 1343 - 1357 (2007/10/02)
1-O-Unsubstituted aldoses afford with halogen-activated nitriles under base catalysis directly O-α- and O-β-glycosyl imidates which can be isolated as stable compounds.Investigations with 2,3,4,6-tetra-O-benzyl- and -acetylglucose (1a, b), trichloroacetonitrile and trifluoroacetonitrile and NaH and K2CO3, respectively, as base have demonstrated, that the β-glucopyranosyl-1-oxido oxygen atom is more nucleophilic (rapid formation of 3a-β, 3b-β, 4a-β, and 4b-β) than the α-glycopyranosyl-1-oxido oxygen atom.Because of the reversibility of these reactions, however,due to the anomeric effect finally the thermodynamically more stable α-imidates 3a-α, 3b-α, 4a-α, and 4b-α are formed exclusively.Therefore O-α- and O-β-glycosyl imidate formation can be conducted highly diastereoselectively. - From trichloroacetonitrile and other 1-O-unsubstituted carbohydrates the imidates 7-α - 13-β were obtained as stable compounds. - Less activated nitriles (chloroacetonitrile, dichloroacetonitrile) have proven not or not so successful in the direct O-glycosyl imidate formation. - N-Aryl ketenimines yielded cleanly base-catalyzed direct O-glycosyl imidate formation.However, because of the irreversibility of this reaction under the reaction conditions only kinetic product formation was observed (leading to the β-imidates 14a-β - 14d-β and 15d-β.Similarly 1-O-unprotected mannose gave only the β-product 16d-β.
