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
[31]   Immunization of mice with a fully synthetic globo H antigen results in antibodies against human cancer cells: A combined chemical-immunological approach to the fashioning of an anticancer vaccine [J].
Ragupathi, G ;
PArk, TK ;
Zhang, SL ;
Kim, IJ ;
Graber, L ;
Adluri, S ;
Lloyd, KO ;
Danishefsky, SJ ;
Livingston, PO .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (1-2) :125-128
[32]   MAJOR SIMPLIFICATIONS IN OLIGOSACCHARIDE SYNTHESES ARISING FROM A SOLID-PHASE BASED METHOD - AN APPLICATION TO THE SYNTHESIS OF THE LEWIS-B ANTIGEN [J].
RANDOLPH, JT ;
MCCLURE, KF ;
DANISHEFSKY, SJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (21) :5712-5719
[33]   SYNTHESIS OF D-ERYTHRO-SPHINGOSINES [J].
SCHMIDT, RR ;
ZIMMERMANN, P .
TETRAHEDRON LETTERS, 1986, 27 (04) :481-484
[34]   Coupling of glycal derived thioethyl glycosyl donors with glycal acceptors. An advance in the scope of the glycal assembly [J].
Seeberger, PH ;
Eckhardt, M ;
Gutteridge, CE ;
Danishefsky, SJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (42) :10064-10072
[35]   SYNTHETIC CARBOHYDRATE VACCINES BASED ON TUMOR-ASSOCIATED ANTIGENS [J].
TOYOKUNI, T ;
SINGHAL, AK .
CHEMICAL SOCIETY REVIEWS, 1995, 24 (04) :231-+
[36]  
WINDMULLER R, 1994, TETRAHEDRON LETT, V35, P7927, DOI 10.1016/S0040-4039(00)78387-0