Abstract:
:Described here is the asymmetric synthesis of iminosugar 2b, a Lipid II analog, designed to mimic the transition state of transglycosylation catalyzed by the bacterial transglycosylase. The high density of functional groups, together with a rich stereochemistry, represents an extraordinary challenge for chemical synthesis. The key 2,6-anti- stereochemistry of the iminosugar ring was established through an iridium-catalyzed asymmetric allylic amination. The developed synthetic route is suitable for the synthesis of focused libraries to enable the structure-activity relationship study and late-stage modification of iminosugar scaffold with variable lipid, peptide and sugar substituents. Compound 2b showed 70% inhibition of transglycosylase from Acinetobacter baumannii, providing a basis for further improvement.
journal_name
Bioorg Med Chem Lettjournal_title
Bioorganic & medicinal chemistry lettersauthors
Wang X,Krasnova L,Wu KB,Wu WS,Cheng TJ,Wong CHdoi
10.1016/j.bmcl.2018.03.035subject
Has Abstractpub_date
2018-09-01 00:00:00pages
2708-2712issue
16eissn
0960-894Xissn
1464-3405pii
S0960-894X(18)30228-2journal_volume
28pub_type
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