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 50 条
  • [1] Total synthesis of the potential anticancer vaccine KH-1 adenocarcinoma antigen
    Prashant P. Deshpande
    Samuel J. Danishefsky
    Nature, 1997, 387 : 164 - 166
  • [2] Total synthesis of the potential anticancer vaccine KH-1 adenocarcinoma antigen
    Deshpande, PP
    Danishefsky, SJ
    NATURE, 1997, 387 (6629) : 164 - 166
  • [3] Erratum: Total synthesis of the potential anticancer vaccine KH-1 adenocarcinoma antigen
    Prashant P. Deshpande
    Samuel J. Danishefsky
    Nature, 1997, 388 : 210 - 210
  • [5] Total synthesis of tumor-associated KH-1 antigen core nonasaccharide via photo-induced glycosylation
    Li, Bo-Han
    Yao, Wenlong
    Yang, Hong
    Wu, Congying
    Xiong, De-Cai
    Yin, Yuxin
    Ye, Xin-Shan
    ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (10): : 1255 - 1259
  • [6] Synthesis of selected LeY and KH-1 analogues:: A medicinal chemistry approach to vaccine optimization
    Spassova, MK
    Bornmann, WG
    Ragupathi, G
    Sukenick, G
    Livingston, PO
    Danishefsky, SJ
    JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (09): : 3383 - 3395
  • [7] A radical cyclization strategy for the concise total synthesis of (+/-)-geissoschizine
    Takayama, H
    Watanabe, F
    Kitajima, M
    Aimi, N
    TETRAHEDRON LETTERS, 1997, 38 (30) : 5307 - 5310
  • [8] A concise synthesis of (±) and a total synthesis of (+)-epiquinamide
    Tong, Sok Teng
    Barker, David
    TETRAHEDRON LETTERS, 2006, 47 (29) : 5017 - 5020
  • [9] A concise total synthesis of (±)-1-epiaustraline
    Donohoe, TJ
    Sintim, HO
    ORGANIC LETTERS, 2004, 6 (12) : 2003 - 2006
  • [10] APPLICATION OF THE GLYCAL ASSEMBLY STRATEGY TO THE SYNTHESIS OF A BRANCHED OLIGOSACCHARIDE - THE 1ST SYNTHESIS OF A COMPLEX SAPONIN
    RANDOLPH, JT
    DANISHEFSKY, SJ
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (18) : 8473 - 8474