Deacetylation Regioselective De Glycals

Bouhroum, Salah; Grondin, Joseph A.; Houdier, Stéphan; Lazrek, H. B.; Rhazi, Mohammed; Tolaimate, Abdelouahad; Vottero, P.

doi:10.1080/07328309108543910

Cited by 5 publications

(1 citation statement)

References 2 publications

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“…Control compound 5 was obtained from xylal 15 16 (Scheme ). Regioselective β ‐galactosylation with trichloroacetimidate 16 ,17 followed by hydrogenation, gave 17 .…”

Section: Methodsmentioning

confidence: 99%

Preorganization of the Bioactive Conformation of Sialyl LewisX Analogues Correlates with Their Affinity to E-Selectin

Thoma

Magnani²,

Patton³

et al. 2001

Angew. Chem.

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Excessive infiltration of leukocytes from blood vessels into surrounding tissues can cause acute or chronic reactions as observed in reperfusion injuries, stroke, psoriasis, rheumatoid Manchester, UK), modified by addition of two pairs of collision gas cells and a low-temperature CI source equipped with a thoriated filament. Typical CI source conditions were as follows: source temperature 100 8C; repeller voltage 0.0 V; ion extraction voltage 8 kV; source pressure 0.05 ± 0.1 Torr. The CAD spectra were recorded with helium as collision gas, admitted into the cell to such a pressure as to reduce the beam intensity by 30 %. The NR experiments were performed in the first pair of collision cells positioned between the magnet and the second electrostatic analyzer, reionization being achieved with O 2 as the collider. Any ions leaving the first collision cell were removed using a high-voltage (1 kV) deflector whose efficiency was checked by control experiments. The NR spectra were averaged over 20 to 50 acquisitions to achieve a satisfactory signal-to-noise ratio. The gases, research-grade products from commercial sources with a stated purity exceeding 99.95 mol %, were used as such. Ozone was prepared from dry O 2 in a commercial ozonizer, collected in a silica trap at 77 K and recovered by controlled warming. Some of the initially pure O 3 desorbed from the trap undergoes dissociation into O 2 in the transfer line and/or in the ion source. Furthermore, trace impurities such as H 2 O and CO 2 are produced by unspecified reactions of O 3 with the transfer line and the source materials. 15 N 2 (98 atom %) was obtained from Aldrich Chemical Co., Inc.

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“…Control compound 5 was obtained from xylal 15 16 (Scheme ). Regioselective β ‐galactosylation with trichloroacetimidate 16 ,17 followed by hydrogenation, gave 17 .…”

Section: Methodsmentioning

confidence: 99%

Preorganization of the Bioactive Conformation of Sialyl LewisX Analogues Correlates with Their Affinity to E-Selectin

Thoma

Magnani²,

Patton³

et al. 2001

Angew. Chem.

View full text Add to dashboard Cite

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Preorganization of the Bioactive Conformation of Sialyl LewisX Analogues Correlates with Their Affinity to E-Selectin

Thoma

Magnani²,

Patton³

et al. 2001

Angew. Chem. Int. Ed.

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It pays to be organized: Steric repulsion between fucose and the methyl substituent of the adjacent tetrahydropyran reduces the distance between galactose and fucose in the E‐selectin antagonist 1 compared to the distance in closely related compounds that lack the methyl group. This effect causes a solution conformation of 1 that already resembles its conformation when bound to E‐selectin and, thus, leads to a significantly improved bioactivity.

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