Reactivity-based one-pot total synthesis of fucose GM1 oligosaccharide: a sialylated antigenic epitope of small-cell lung cancer.
The total synthesis of the sialic acid-containing antigenic epitope fucose GM(1) (Fuc-GM(1)) by an improved reactivity-based one-pot synthetic strategy is reported. Based on a thioglycoside reactivity database, three saccharide building blocks, 3, 4, and 5, were designed and prepared to incorporate a descending order of reactivity toward thiophilic activation. Using the reactivity-based one-pot synthetic method, the fully protected Fuc-GM(1) glycoside 2 was furnished in a facile manner, which was globally deprotected to give the Fuc-GM(1) glycoside 1. In addition, using the promoter system 1-(benzensulfinyl)piperidinetrifluoromethanesulfonic anhydride, the product yield was improved and the reaction time was reduced in comparison with the N-iodosuccinimidetrifluoromethanesulfonic acid- and dimethyl (thiomethyl) sulfonium trifluoromethanesulfonate-promoted systems.
Mong
Tony Kwok-Kong
TK
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.
Lee
Hing-Ken
HK
Duron
Sergio G
SG
Wong
Chi-Huey
CH
D002240:Carbohydrate Sequence; D018288:Carcinoma, Small Cell / Q000276:immunology / Q000378:metabolism*; D004187:Disaccharides; D000939:Epitopes; D005643:Fucose / Q000737:chemistry*; D008175:Lung Neoplasms / Q000276:immunology / Q000378:metabolism*; D008969:Molecular Sequence Data; D019158:N-Acetylneuraminic Acid / Q000737:chemistry*; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry*
D004187:Disaccharides; D000939:Epitopes; D009844:Oligosaccharides; D005643:Fucose; C037563:G(M1)-oligosaccharide; D019158:N-Acetylneuraminic Acid