Synthesis of double C-glycoside analogue of sTn

被引:16
作者
Ress, DK
Baytas, SN
Wang, Q
Muñoz, EM
Tokuzoki, K
Tomiyama, H
Linhardt, RJ [1 ]
机构
[1] Univ Iowa, Div Med & Nat Prod Chem, Iowa City, IA 52242 USA
[2] Kotobuki Pharmaceut Co Ltd, Nagano, Japan
[3] Rensselaer Polytech Inst, Dept Biol, Troy, NY 12180 USA
[4] Rensselaer Polytech Inst, Dept Biol & Chem Engn, Troy, NY 12180 USA
关键词
D O I
10.1021/jo050691n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A sTn double C-glycoside, sTn analogue 2, was synthesized using samarium chemistry developed in our laboratory. Complications in the oxidation reaction affording aldehyde acceptor were overcome by double protection of amide and the use of a room-temperature ionic liquid as solvent. Studies are underway to conjugate the sTn double C-glycoside hapten 2 to KLH carrier protein for biological evaluation as a vaccine.
引用
收藏
页码:8197 / 8200
页数:4
相关论文
共 32 条
[21]  
Miyajima K, 1998, CHEM PHARM BULL, V46, P1676
[22]   ATTACHMENT OF OLIGOSACCHARIDES TO PEPTIDE ANTIGEN PROFOUNDLY AFFECTS BINDING TO MAJOR HISTOCOMPATIBILITY COMPLEX CLASS-II MOLECULES AND PEPTIDE IMMUNOGENICITY [J].
MOURITSEN, S ;
MELDAL, M ;
CHRISTIANSENBRAMS, I ;
ELSNER, H ;
WERDELIN, O .
EUROPEAN JOURNAL OF IMMUNOLOGY, 1994, 24 (05) :1066-1072
[23]  
Murugesan S, 2003, SYNLETT, P1283
[25]   Capsule switching of Neisseria meningitidis [J].
Swartley, JS ;
Marfin, AA ;
Edupuganti, S ;
Liu, LJ ;
Cieslak, P ;
Perkins, B ;
Wenger, JD ;
Stephens, DS .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1997, 94 (01) :271-276
[26]  
TOYOKUNI T, 1995, CHEM SOC REV, P231
[27]   DIVERSITY IN THE SIALIC ACIDS [J].
VARKI, A .
GLYCOBIOLOGY, 1992, 2 (01) :25-40
[28]   Diastereocontrolled synthesis of carbon glycosides of N-acetylneuraminic acid via glycosyl samarium(III) intermediates [J].
Vlahov, IR ;
Vlahova, PI ;
Linhardt, RJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (06) :1480-1481
[29]   Recyclable 2nd generation ionic liquids as green solvents for the oxidation of alcohols with hypervalent iodine reagents [J].
Yadav, JS ;
Reddy, BVS ;
Basak, AK ;
Narsaiah, AV .
TETRAHEDRON, 2004, 60 (09) :2131-2135
[30]  
Yu CS, 2001, ANGEW CHEM INT EDIT, V40, P2900, DOI 10.1002/1521-3773(20010803)40:15<2900::AID-ANIE2900>3.0.CO