Stereoselective Synthesis of 2‑Acetamido-1,2-dideoxyallonojirimycin (DAJNAc), a New Potent Hexosaminidase Inhibitor
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-acetylgluco...
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| Veröffentlicht in: | Organic letters 2013-07, Vol.15 (14), p.3638-3641 |
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| container_issue | 14 |
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| container_title | Organic letters |
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| creator | de la Fuente, Alex Martin, Ruben Mena-Barragán, Teresa Verdaguer, Xavier García Fernández, José M Ortiz Mellet, Carmen Riera, Antoni |
| description | 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. |
| doi_str_mv | 10.1021/ol401517x |
| format | Article |
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| ispartof | Organic letters, 2013-07, Vol.15 (14), p.3638-3641 |
| issn | 1523-7060 1523-7052 |
| language | eng |
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| source | ACS Publications; MEDLINE |
| subjects | 1-Deoxynojirimycin - analogs & derivatives 1-Deoxynojirimycin - chemical synthesis 1-Deoxynojirimycin - chemistry beta-N-Acetylhexosaminidases - chemical synthesis beta-N-Acetylhexosaminidases - chemistry Female Hexosaminidases - analysis Hexosaminidases - chemistry Humans Pregnancy Stereoisomerism |
| title | Stereoselective Synthesis of 2‑Acetamido-1,2-dideoxyallonojirimycin (DAJNAc), a New Potent Hexosaminidase Inhibitor |
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