Improving glycopeptide synthesis: a convenient protocol for the preparation of beta-glycosylamines and the synthesis of glycopeptides.
[reaction: see text] Herein we apply a recently introduced protocol using ammonium carbamate in methanol to the amination of crude chitobiose leading to 1,beta-aminochitobiose. This simple, one-step procedure allows a facile preparation of unstable glycosylamines in contrast to the commonly implemented ammonium bicarbonate based amination of water-soluble carbohydrates. The new amination protocol leads to an improved synthesis of the key chitobiosyl-asparagine building block for the SPPS of glycopeptides. The utility of the method is demonstrated with the synthesis of a 39-amino acid glycoprotein.
Hackenberger
Christian P R
CP
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
O'Reilly
Mary K
MK
Imperiali
Barbara
B
D000586:Amination; D000596:Amino Acids / Q000138:chemical synthesis*; D000606:Amino Sugars / Q000138:chemical synthesis; D001216:Asparagine / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods*; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D006020:Glycopeptides / Q000138:chemical synthesis*; D015394:Molecular Structure
D000596:Amino Acids; D000606:Amino Sugars; D004187:Disaccharides; D006020:Glycopeptides; C032438:chitobiose; D001216:Asparagine