Organic synthesis in pursuit of immunology: large-scale synthesis of peracetylated GM2 glycosylamino acid for preparation of a multiantigenic prostate cancer vaccine.
We describe herein the stereo-controlled, large-scale synthesis of peracetylated GM2 glycosylamino acid. Key features of the synthesis include a newly modified [1+3] coupling reaction and an olefin cross-metathesis-hydrogenation sequence. The GM2 glycosylamino acid is now ready for incorporation into a hexavalent prostate cancer vaccine construct.
Cho
Young Shin
YS
Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, NY 10021, USA.
Wan
Qian
Q
Danishefsky
Samuel J
SJ
D000107:Acetylation; D000596:Amino Acids / Q000138:chemical synthesis*; D019496:Cancer Vaccines / Q000138:chemical synthesis* / Q000276:immunology; D002240:Carbohydrate Sequence; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D008969:Molecular Sequence Data; D011471:Prostatic Neoplasms / Q000628:therapy*; D013055:Spectrophotometry, Infrared
D000596:Amino Acids; D019496:Cancer Vaccines