Strategy in oligosaccharide synthesis: An application to a concise total synthesis of the KH-1(adenocarcinoma) antigen

被引:47
作者
Deshpande, PP
Kim, HM
Zatorski, A
Park, TK
Ragupathi, G
Livingston, PO
Live, D
Danishefsky, SJ
机构
[1] Sloan Kettering Inst Canc Res, Bioorgan Chem Lab, New York, NY 10021 USA
[2] Sloan Kettering Inst Canc Res, Lab Tumor Vaccinol, New York, NY 10021 USA
[3] Sloan Kettering Inst Canc Res, Lab Nucl Acid & Prot Struct, New York, NY 10021 USA
[4] Columbia Univ, Dept Chem, New York, NY 10027 USA
关键词
D O I
10.1021/ja9725864
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A concise and potentially practical synthesis of the title compound has been achieved. The route features a high degree of convergence and economy of synthetic operations. A key step is the concurrent introductory addition of three alpha-L-fucosyl residues at required hydroxyl acceptor sites (see 37 --> 39). Conjugation to carrier protein was achieved, and a route to include truncated structures for investigations for antibody specificity was accomplished.
引用
收藏
页码:1600 / 1614
页数:15
相关论文
共 36 条
[11]   AN UNEXPECTED SIALYLATION - TOTAL SYNTHESES OF G(M4) AND A POSITIONAL ISOMER [J].
GERVAY, J ;
PETERSON, JM ;
ORIYAMA, T ;
DANISHEFSKY, SJ .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (20) :5465-5468
[12]   SULFONAMIDOGLYCOSYLATION OF GLYCALS - A ROUTE TO OLIGOSACCHARIDES WITH 2-AMINOHEXOSE SUBUNITS [J].
GRIFFITH, DA ;
DANISHEFSKY, SJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (15) :5811-5819
[13]  
HAKOMORI S, 1985, CANCER RES, V45, P2405
[14]   Glycosphingolipid antigens and cancer therapy [J].
Hakomori, S ;
Zhang, YM .
CHEMISTRY & BIOLOGY, 1997, 4 (02) :97-104
[15]  
HAKOMORI SI, 1989, ADV CANCER RES, V52, P257
[16]  
HAKOMORI SI, 1991, CANCER CELL-MON REV, V3, P461
[17]   SYNTHESIS OF A TRIFUCOSYL LEY HEPTASACCHARIDE CORRESPONDING TO A TUMOR-ASSOCIATED GLYCOLIPID [J].
HELLAND, AC ;
NILSSON, M ;
NORBERG, T .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1992, 11 (01) :77-88
[18]   Glycosylimidates .79. A versatile synthesis of the lactoneo-series antigens - Synthesis of sialyl dimer Lewis X and of dimer Lewis Y [J].
Hummel, G ;
Schmidt, RR .
TETRAHEDRON LETTERS, 1997, 38 (07) :1173-1176
[19]  
JEFFERY PD, 1995, NAT STRUCT BIOL, V2, P456
[20]  
KAIZU T, 1986, J BIOL CHEM, V261, P1254