Synthesis of oxime-linked mucin mimics containing the tumor-related TN and sialyl TN antigens

被引:59
作者
Marcaurelle, LA
Shin, YS
Goon, S
Bertozzi, CR [1 ]
机构
[1] Univ Calif Berkeley, Ctr New Direct Organ Synth, Dept Chem, Berkeley, CA 94720 USA
[2] Univ Calif Berkeley, Ctr New Direct Organ Synth, Dept Mol & Cell Biol, Berkeley, CA 94720 USA
[3] Univ Calif Berkeley, Howard Hughes Med Inst, Berkeley, CA 94720 USA
关键词
D O I
10.1021/ol0166247
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The synthesis of oxime-linked mucin mimics was accomplished via the incorporation of multiple ketone residues into a peptide followed by reaction with aminooxy sugars corresponding to the tumor-related T-N and sialyl T-N (STN) antigens.
引用
收藏
页码:3691 / 3694
页数:4
相关论文
共 35 条
[1]   A total synthesis of the methyl glycoside of ganglioside GM1 [J].
Bhattacharya, SK ;
Danishefsky, SJ .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (01) :144-151
[2]   MECHANISMS UNDERLYING ABERRANT GLYCOSYLATION OF MUC1 MUCIN IN BREAST-CANCER CELLS [J].
BROCKHAUSEN, I ;
YANG, JM ;
BURCHELL, J ;
WHITEHOUSE, C ;
TAYLORPAPADIMITRIOU, J .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 1995, 233 (02) :607-617
[3]   STEREOSELECTIVE PHASE-TRANSFER-CATALYZED SYNTHESES OF GLYCOSYLOXYSUCCINIMIDES AND THEIR TRANSFORMATIONS INTO GLYCOPROBES [J].
CAO, SD ;
TROPPER, FD ;
ROY, R .
TETRAHEDRON, 1995, 51 (24) :6679-6686
[4]  
CARRAWAY K L, 1991, Glycobiology, V1, P131, DOI 10.1093/glycob/1.2.131
[5]  
Danishefsky SJ, 2000, ANGEW CHEM INT EDIT, V39, P836, DOI 10.1002/(SICI)1521-3773(20000303)39:5<836::AID-ANIE836>3.0.CO
[6]  
2-I
[7]   Synthesis of native proteins by chemical ligation [J].
Dawson, PE ;
Kent, SBH .
ANNUAL REVIEW OF BIOCHEMISTRY, 2000, 69 :923-960
[8]   Preparation of Tn and sialyl Tn building blocks used in Fmoc solid-phase synthesis of glycopeptide fragments from HIV gp120 [J].
Elofsson, M ;
Salvador, LA ;
Kihlberg, J .
TETRAHEDRON, 1997, 53 (01) :369-390
[9]   Chemoenzymatic synthesis of derivatives of a T-cell-stimulating peptide which carry tumor-associated carbohydrate antigens [J].
George, SK ;
Holm, B ;
Reis, CA ;
Schwientek, T ;
Clausen, H ;
Kihlberg, J .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (08) :880-885
[10]   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