Synthesis and glycosidase inhibition of conformationally locked DNJ and DMJ derivatives exploiting a 2-oxo-C-allyl iminosugar.
In: Organic & biomolecular chemistry, Jg. 17 (2019-08-14), Heft 30, S. 7204-7214
academicJournal
Zugriff:
A series of analogs of the iminosugars 1-deoxynojirimycin (DNJ) and 1-deoxymannojirimycin (DMJ), in which an extra five or six-membered ring has been fused to the C1-C2 bond have been prepared. The synthetic strategy exploits a key 2-keto-C-allyl iminosugar, easily accessible from gluconolactam, which upon Grignard addition and RCM furnishes a bicyclic scaffold that can be further hydroxylated at the C[double bond, length as m-dash]C bond. This strategy furnished DNJ mimics with the piperidine ring locked in a 1 C 4 conformation with all substituents in axial orientation when fused to a six-membered ring. Addition of an extra ring to DNJ and DMJ motif proved to strongly modify the glycosidase inhibition profile of the parent iminosugars leading to modest inhibitors. The 2-keto-C-allyl iminosugar scaffold was further used to access N-acetylglycosamine analogs via oxime formation.
Titel: |
Synthesis and glycosidase inhibition of conformationally locked DNJ and DMJ derivatives exploiting a 2-oxo-C-allyl iminosugar.
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Autor/in / Beteiligte Person: | Foucart, Q ; Shimadate, Y ; Marrot, J ; Kato, A ; Désiré, J ; Blériot, Y |
Zeitschrift: | Organic & biomolecular chemistry, Jg. 17 (2019-08-14), Heft 30, S. 7204-7214 |
Veröffentlichung: | Cambridge, UK : Royal Society of Chemistry, c2003-, 2019 |
Medientyp: | academicJournal |
ISSN: | 1477-0539 (electronic) |
DOI: | 10.1039/c9ob01402k |
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