Chemical synthesis of normal and transformed PSA glycopeptides.
Chemical syntheses are reported for prostate specific antigen (PSA) N-linked glycopeptide fragments consisting of an uneicosapeptide (residues 27-47 of PSA) with di-, tri-, and tetrabranched N-acetyllactosamine-type glycans. The syntheses involve simultaneous, multiple glycosylations of the corresponding pentasaccharide acceptors prepared from a common trisaccharide precursor. Globally deprotected glycans are aminated and then aspartylated with a hexapeptide, which is then extended using native chemical ligation (NCL). The glycopeptides will be used for the generation of antibodies that may form the basis for a new prostate cancer diagnostic assay.
Dudkin
Vadim Y
VY
Laboratory for Bioorganic Chemistry, The Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, New York 10021, USA.
Miller
Justin S
JS
Danishefsky
Samuel J
SJ
D000595:Amino Acid Sequence; D000606:Amino Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D002240:Carbohydrate Sequence; D006020:Glycopeptides / Q000138:chemical synthesis*; D008969:Molecular Sequence Data; D011134:Polysaccharides / Q000138:chemical synthesis; D017430:Prostate-Specific Antigen / Q000138:chemical synthesis*
D000606:Amino Sugars; D006020:Glycopeptides; D011134:Polysaccharides; C000458:N-acetyllactosamine; D017430:Prostate-Specific Antigen