N-trifluoroacetyl sialyl phosphite donors for the synthesis of α(2 → 9) oligosialic acids

被引:57
作者
Lin, CC [1 ]
Huang, KT
Lin, CC [1 ]
机构
[1] Acad Sinica, Inst Chem, Taipei 115, Taiwan
[2] Acad Sinica, Genom Res Ctr, Taipei 115, Taiwan
[3] Natl Tsing Hua Univ, Dept Chem, Hsinchu, Taiwan
关键词
D O I
10.1021/ol0515210
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new method for the synthesis of alpha(2 -> 9) oligosialic acids is developed using phosphite sialyl donors that are protected with a C-5 N-trifluoroacetyl (NHTFA) substituent. Compared with conventional donors, these donors gave a higher degree of alpha-anomeric selectivity during glycosidic bond formation and better yields during iterative sialylation in the synthesis of oligosialic acids.
引用
收藏
页码:4169 / 4172
页数:4
相关论文
共 44 条
[31]   Polysialic acid:: three-dimensional structure, biosynthesis and function [J].
Mühlenhoff, M ;
Eckhardt, M ;
Gerardy-Schahn, R .
CURRENT OPINION IN STRUCTURAL BIOLOGY, 1998, 8 (05) :558-564
[32]  
Nicolaou K.C., 1997, PREPARATIVE CARBOHYD, P313
[33]   SYNTHETIC STUDIES ON GANGLIOSIDES .3. GLYCOSYLATION OF 4,7,8,9-TETRA-O-ACETYL-2-DEOXY-2-BETA,3-BETA-EPOXY-N-ACETYLNEURAMINIC ACID METHYL-ESTER [J].
OKAMOTO, K ;
KONDO, T ;
GOTO, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1987, 60 (02) :637-643
[34]   Synthesis and immunological properties of N-modified GM3 antigens as therapeutic cancer vaccines [J].
Pan, YB ;
Chefalo, P ;
Nagy, N ;
Harding, C ;
Guo, ZW .
JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (03) :875-883
[35]   Sialic acid donors: Chemical synthesis and glycosylation [J].
Ress, DK ;
Linhardt, RJ .
CURRENT ORGANIC SYNTHESIS, 2004, 1 (01) :31-46
[36]  
Rosenberg A., 1995, BIOL SIALIC ACIDS
[37]  
Schneider R, 2001, EUR J ORG CHEM, V2001, P1655
[38]   A new method for the formation of the alpha-glycoside bond of sialyl conjugates based on long-range participation [J].
Takahashi, T ;
Tsukamoto, H ;
Yamada, H .
TETRAHEDRON LETTERS, 1997, 38 (47) :8223-8226
[39]   One-pot synthesis of sialo-containing glycosyl amino acids by use of an N-trichloroethoxycarbonyl-β-thiophenyl sialoside [J].
Tanaka, H ;
Adachi, M ;
Takahashi, T .
CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (03) :849-862
[40]   A FACILE PREPARATION OF ALKYL ALPHA-GLYCOSIDES OF THE METHYL-ESTER OF N-ACETYL-D-NEURAMINIC ACID [J].
VANDERVLEUGEL, DJM ;
VANHEESWIJK, WAR ;
VLIEGENTHART, JFG .
CARBOHYDRATE RESEARCH, 1982, 102 (APR) :121-130