Abstract
A practical synthesis of the previously unreported N-acetyl-D-allosamine glycomimetic DAJNAc is described. The reaction sequence involves Pd-catalyzed allylic substitution by phthalimide in an azaheterobicyclic scaffold as the key step. The new iminosugar resulted in being a stronger β-N-acetylglucosaminidase (human placenta) competitive inhibitor than the D-gluco (DNJNAc) and D-galacto (DGJNAc) stereoisomers.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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1-Deoxynojirimycin / analogs & derivatives*
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1-Deoxynojirimycin / chemical synthesis
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1-Deoxynojirimycin / chemistry
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Female
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Hexosaminidases / analysis*
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Hexosaminidases / chemistry*
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Humans
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Pregnancy
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Stereoisomerism
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beta-N-Acetylhexosaminidases / chemical synthesis*
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beta-N-Acetylhexosaminidases / chemistry*
Substances
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2-acetamido-1,2-dideoxyallonojirimycin
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1-Deoxynojirimycin
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Hexosaminidases
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beta-N-Acetylhexosaminidases