Molecular transporter between polymer platforms: Highly efficient chemoenzymatic glycopeptide synthesis by the combined use of solid-phase and water-soluble polymer supports

被引:32
作者
Fumoto, M
Hinou, H
Matsushita, T
Kurogochi, M
Ohta, T
Ito, T
Yamada, K
Takimoto, A
Kondo, H
Inazu, T
Nishimura, SI [1 ]
机构
[1] Natl Inst Adv Ind Sci & Technol, Res Ctr Glycosci, Glycochemosynth Team, Sapporo, Hokkaido 0628517, Japan
[2] Hokkaido Univ, Grad Sch Sci, Div Biol Sci, Sapporo, Hokkaido 0010021, Japan
[3] Res Assoc Biotechnol, Minato Ku, Tokyo 1050003, Japan
[4] Shionogi & Co Ltd, Chuo Ku, Osaka 5410045, Japan
[5] Hitachi High Technol Co, Minato Ku, Tokyo 1058717, Japan
[6] Sch Engn, Dept Appl Chem, Kanagawa 2591292, Japan
[7] Inst Glychotechnol, Kanagawa 2591292, Japan
关键词
enzymes; glycopeptides; polymers; solid-phase synthesis; synthetic methods;
D O I
10.1002/anie.200463065
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Figure Presented) The molecule standing at platform one ...: Rapid glycopeptide synthesis is achieved with a heterobifunctional "molecular transporter" (see scheme), which interfaces two types of polymer platforms for combined chemical and enzymatic synthesis. This linker allows both chemoselective blotting and photoselective cleavage of the glycopeptides. Red: sugar residues; green: amino acid residues. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:2534 / 2537
页数:4
相关论文
共 28 条
[21]   Automated solid-phase synthesis of oligosaccharides [J].
Plante, OJ ;
Palmacci, ER ;
Seeberger, PH .
SCIENCE, 2001, 291 (5508) :1523-1527
[22]   Chemoenzymatic solution- and solid-phase synthesis of O-glycopeptides of the mucin domain of MAdCAM-1. A general route to O-LacNAc, O-sialyl-LacNAc, and O-sialyl-Lewis-X peptides [J].
Seitz, O ;
Wong, CH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (38) :8766-8776
[23]   POLYMER SUPPORT OLIGONUCLEOTIDE SYNTHESIS .18. USE OF BETA-CYANOETHYL-N,N-DIALKYLAMINO-/N-MORPHOLINO PHOSPHORAMIDITE OF DEOXYNUCLEOSIDES FOR THE SYNTHESIS OF DNA FRAGMENTS SIMPLIFYING DEPROTECTION AND ISOLATION OF THE FINAL PRODUCT [J].
SINHA, ND ;
BIERNAT, J ;
MCMANUS, J ;
KOSTER, H .
NUCLEIC ACIDS RESEARCH, 1984, 12 (11) :4539-4557
[24]  
St Hilaire PM, 2000, ANGEW CHEM INT EDIT, V39, P1162, DOI 10.1002/(SICI)1521-3773(20000403)39:7<1162::AID-ANIE1162>3.0.CO
[25]  
2-6
[26]  
Toda A, 2002, ADV SYNTH CATAL, V344, P61
[27]   High performance polymer supports for enzyme-assisted synthesis of glycoconjugates [J].
Yamada, K ;
Fujita, E ;
Nishimura, SI .
CARBOHYDRATE RESEARCH, 1997, 305 (3-4) :443-461
[28]   ENZYMIC-SYNTHESIS OF OLIGOSACCHARIDES ON A POLYMER SUPPORT - LIGHT-SENSITIVE, SUBSTITUTED POLYACRYLAMIDE BEADS [J].
ZEHAVI, U ;
SADEH, S ;
HERCHMAN, M .
CARBOHYDRATE RESEARCH, 1983, 124 (01) :23-34