Solid-phase synthesis of CD52 glycopeptide and an efficient route to Asn-core pentasaccharide conjugate.
The intact peptide sequence (18) as well as its glycoform carrying an N-linked core pentasaccharide (1) of CD52 antigen were prepared by means of solid-phase synthesis employing Fmoc-amino acids and benzyl-protected oligosaccharide-asparagine conjugate (3) as building blocks. It was concluded that the pentasaccharide structure had little influence on further peptide elongation in solid-phase synthesis and the benzylated pentasaccharide moiety was sufficiently stable to the 95% TFA acidic conditions used to release glycopeptide from the supporting resin. The paper also describes an efficient route leading to asparagine-core pentasaccharide conjugate (3) which was prepared in seven steps for an overall yield of 23% from monosaccharide units 5, 6, 7 and 8.
Guo
Z W
ZW
Institute of Physical and Chemical Research (RIKEN), Saitama, Japan.
Nakahara
Y
Y
Nakahara
Y
Y
Ogawa
T
T
D015703:Antigens, CD / Q000737:chemistry*; D000951:Antigens, Neoplasm; D001216:Asparagine / Q000737:chemistry; D000074301:CD52 Antigen; D002240:Carbohydrate Sequence; D006020:Glycopeptides / Q000138:chemical synthesis*; D006023:Glycoproteins / Q000737:chemistry*; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D009005:Monosaccharides / Q000737:chemistry; D013329:Structure-Activity Relationship
D015703:Antigens, CD; D000951:Antigens, Neoplasm; D000074301:CD52 Antigen; C000613862:CD52 protein, human; D006020:Glycopeptides; D006023:Glycoproteins; D009005:Monosaccharides; D001216:Asparagine