Open AccessVersatile Approaches to Sugar Amino Acid Building Blocks as Precursors of Glycopeptides
Author(s) -
Christelle Jablonski-Lorin,
Matthias Nold,
Arthur Bodenmüller,
Ernst Hungerbühler
Publication year - 2007
Publication title -
chimia
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.387
H-Index - 55
eISSN - 2673-2424
pISSN - 0009-4293
DOI - 10.2533/chimia.2006.286
Subject(s) - glycopeptide , monosaccharide , chemistry , amino acid , template , sugar , anomer , amino sugar , azide , glycal , peptide , combinatorial chemistry , organic chemistry , biochemistry , stereoselectivity , catalysis , nanotechnology , materials science , antibiotics
The synthesis of monosaccharide units functionalised with different amino acids is described herein. Sugar amino acid templates linked at position 6 of the sugar were prepared by various nucleophilic substitutions introducing a spacer of variable length or by traceless Staudinger ligation. Sugar amino acid templates attached at the anomeric position and representing a class of precursors of glycopeptides were synthesized in three steps via addition of a solution of trimethylsilylnitrate-trimethylsilylazide on a glycal, followed by subsequent reduction of the sugar azide and coupling with diverse amino acids.