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Synthesis of Fluorescent and Radioactive Analogues of Two Lactosylceramides and Glucosylceramide Containing β-Thioglycosidic Bonds That Are Resistant to Enzymatic Degradation by Bernd Albrecht; Ute Pütz; Günter Schwarzmann is a Biochemistry, Genetics and Molecular Biology article available to read on EtoBox.

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Condensation of 2-S-(2,3,4,6-tetra-O-acetyl-/3-D-galactopyranosyl)-2-thiopseudourea hydrobromide with 2,3,6-tri-O-benzoyl-4-O-trifluoromethylsulfonyl-/3-o-galactopyranosyl-(1 ~ 1)-(2S,3R,4E)-3-O-benzoyl-2-dichloroacetamido-4-octadecen-l,3-diol afforded S-(2,3,4,6-tetra-Oacetyl-/3-D-galactopyranosyl)-(1 ~ 4)-2,3,6-tri-O-benzoyl-4-thio-/3-o-glucopyranosyl-(1 ~ 1)-(2S, 3R,4E)-3-O -benzoyl-2-dichloroacetamido-4-octadecen-l,3-diol in good yield. Removal of the protecting groups, followed by selective N-acylation of the sphingosine amino group with either a fluorescent or a radioactive fatty acid, gave labeled lactosylceramide analogues in good yield. Since these products contained a /3-thioglycosidic bond between the two sugar moieties, they were totally resistant to the action of acid lysosomal glycosidases. Likewise, condensation of 2-S-(2,3,4,6-tetra-O-acetyl-/3-D-glucopyranosyl)-2-thiopseudourea hydrobromide and 2,3,4,6-tetra-Oacetyl-/3-D-galactopyranosyl-(1 ---, 4)-2,3,6-tri-O-acetyl-l-S-acetyl-l-thio-/3-D-glucopyranose with (2R,3R,4E)-3-O-benzoyl-2-dichloroacetamido-l-iodo-4-octadecen-3-ol in methanolic sodium acetate afforded the corresponding /3-thioglycosides 14 and 16, respect

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Author

Bernd Albrecht; Ute Pütz; Günter Schwarzmann

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0008-6215)

Published

1995

Language

EN

Field

Biochemistry, Genetics and Molecular Biology (Life Sciences)