Regioselective syntheses of beta-N-linked glycoaminoacids and glycopeptides
Alan R Katritzky1, Tamari Narindoshvili, Bogdan Draghici
1Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, USA. katritzky@chem.ufl.edu
Abstract:
Acylation of tetra-O-pivaloyl-beta-D-galactopyranosylamine 2 by readily available N- (Cbz or Fmoc-alpha-aminoacyl) benzotriazoles under microwave irradiation proceeded diastereoselectively to give beta-N-glycoaminoacids 3a-d, (3c+3c') (compound numbers written within brackets represent a racemate or a diastereomeric mixture; compound numbers without brackets represent a single enantiomer) (83-92%), and glycosylated asparagine building block 9 (65%). N-Cbz-Protected peptidoylbenzotriazoles 4a-c similarly afforded beta-N-glycodipeptides 5a-c (76-81%). Regiospecific beta-N-linkage formation was established by 1D and 2D NMR techniques for 3b.
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