Synthesis of aza-analogues of the glycosylated tyrosine portion of mannopeptimycin-E.
Two C4' amido disaccharide analogues of mannopeptimycin-E were synthesized via an iterative palladium glycosylation sequence. The stereoselective synthesis of the C4' acylated 1,4-alpha,alpha-manno,manno-amido disaccharide has been achieved in ten steps from a protected d-tyrosine. The path relies upon a regio- and diastereoselective palladium-catalyzed azide substitution reaction. The competence of the synthesis is demonstrated by the good overall yield (21%) from protected tyrosine.
Guppi
Sanjeeva R
SR
Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA.
O'Doherty
George A
GA
D000498:Allyl Compounds / Q000737:chemistry; D000577:Amides / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D004187:Disaccharides / Q000138:chemical synthesis / Q000737:chemistry; D006020:Glycopeptides / Q000138:chemical synthesis / Q000737:chemistry*; D006031:Glycosylation; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry; D014443:Tyrosine / Q000737:chemistry*
D000498:Allyl Compounds; D000577:Amides; D000588:Amines; D001372:Aza Compounds; D004187:Disaccharides; D006020:Glycopeptides; C516133:mannopeptimycin-E; D014443:Tyrosine; D010100:Oxygen