Preparative acetonation of pyranoid, vicinal trans-glycols under kinetic control: methyl 2,3:4,6-di-O-isopropylidene-α- and -β-d-glucopyranoside

DEBOST, J.-L.; Gelas, Jacques; Horton, Derek; Mols, Ole

doi:10.1016/0008-6215(84)85169-1

Cited by 40 publications

(9 citation statements)

References 21 publications

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“…The reaction of dextran with 2-methoxypropene in the presence of an acid catalyst leads to the formation of both cyclic and acyclic acetals (14,15), causing a switch in solubility and providing a trigger for acid-mediated degradation (Fig. 1A) (13).…”

Section: Resultsmentioning

confidence: 99%

Acetalated dextran is a chemically and biologically tunable material for particulate immunotherapy

Broaders

Cohen

Beaudette

et al. 2009

Proc. Natl. Acad. Sci. U.S.A.

267

379

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Materials that combine facile synthesis, simple tuning of degradation rate, processability, and biocompatibility are in high demand for use in biomedical applications. We report on acetalated dextran, a biocompatible material that can be formed into microparticles with degradation rates that are tunable over 2 orders of magnitude depending on the degree and type of acetal modification. Varying the degradation rate produces particles that perform better than poly(lactic-co-glycolic acid) and iron oxide, two commonly studied materials used for particulate immunotherapy, in major histocompatibility complex class I (MHC I) and MHC II presentation assays. Modulating the material properties leads to antigen presentation on MHC I via pathways that are dependent or independent of the transporter associated with antigen processing. To the best of our knowledge, this is the only example of a material that can be tuned to operate on different immunological pathways while maximizing immunological presentation.acid-sensitive ͉ biocompatible ͉ encapsulation ͉ polymer ͉ vaccine

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Section: Resultsmentioning

confidence: 99%

Acetalated dextran is a chemically and biologically tunable material for particulate immunotherapy

Broaders

Cohen

Beaudette

et al. 2009

Proc. Natl. Acad. Sci. U.S.A.

267

379

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“…This 2,3-isopropylidene trans -acetal bridge has been corroborated to be formed via a kinetic control. [ 23 ] The linear acetal (LA) units, however, should be mainly produced by the primary hydroxyls of CD. Matrix-assisted laser desorption/ionization-time of fl ight (MALDI-ToF) mass spectrommetry and corresponding assignments according to molecular weights (MWs) and acetal structures, shown in Figure S4a in the Supporting Information, provided additional structural information on 1 .…”

Section: Doi: 101002/adma201100679mentioning

confidence: 99%

Facile Engineering of Biocompatible Materials with pH‐Modulated Degradability

Zhang

Jia

et al. 2011

Advanced Materials

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“…In Scheme 1, methyl /3-D-glucopyranoside was converted to 4,6-isopropylidene derivative (1) in 75% yield [6]. Compound I was fluorinated using DAST and methyl 3-deoxy-3-ftuoro-4,6-O,isopropylidene-~-D-al-lopyranoside (2) was obtained in 12% yield.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and X-ray crystal structure of 3-deoxy-3-fluoro-β-D-allopyranoside

et al. 1997

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The synthesis of a novel compound, 3-deoxy-3-fluoro-/3-D-allopyranoside, is described. It involves blocking the 4-and 6-positions of allose to cause fluorination only at the 3-position. This six-step synthesis gave pure crystalline compound in a 5% overall yield. The crystal structure, determined by X-ray diffraction, confirmed the chemical formula and configuration of the product. It showed that the C--F bond is axial, while the C--(OH) bonds are equatorial. The overall conformation of this fluoroallose is similar to that of allose (Acta Cryst. 1984, C40, 1863 (with OH instead of F), but the packing in the two crystals is different in the region of C3, the site of chemical variation.

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Preparative acetonation of pyranoid, vicinal trans-glycols under kinetic control: methyl 2,3:4,6-di-O-isopropylidene-α- and -β-d-glucopyranoside

Cited by 40 publications

References 21 publications

Acetalated dextran is a chemically and biologically tunable material for particulate immunotherapy

Acetalated dextran is a chemically and biologically tunable material for particulate immunotherapy

Facile Engineering of Biocompatible Materials with pH‐Modulated Degradability

Synthesis and X-ray crystal structure of 3-deoxy-3-fluoro-β-D-allopyranoside

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