Rapid synthesis of a glycosylphosphatidylinositol-based malaria vaccine using automated solid-phase oligosaccharide synthesis

被引：96

作者：

Hewitt, MC ^{[1
]}

Snyder, DA ^{[1
]}

Seeberger, PH ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 45期

关键词：

D O I：

10.1021/ja027538k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Described is an automated synthesis of hexasaccharicle malarial toxin 1, currently under development as a malaria vaccine candidate. Using a combination of automated solid-phase methods and solution-phase fragment coupling, the target glycosylphosphaticlylincisitol was assembled in a matter of days, compared with several weeks for a comparable solution-phase synthesis.

引用

收藏

页码：13434 / 13436

页数：3

相关论文

共 25 条

[1] Solid-phase oligosaccharide synthesis: Preparation of complex structures using a novel linker and different glycosylating agents [J].

Andrade, RB ;

Plante, OJ ;

Melean, LG ;

Seeberger, PH .

ORGANIC LETTERS, 1999, 1 (11) :1811-1814

[2]

Baeschlin DK, 2000, CHEM-EUR J, V6, P172, DOI 10.1002/(SICI)1521-3765(20000103)6:1<172::AID-CHEM172>3.3.CO

[3]

2-X

[4] Rapid assembly of oligosaccharides: 1,2-diacetal-mediated reactivity tuning in the coupling of glycosyl fluorides [J].

Baeschlin, DK ;

Green, LG ;

Hahn, MG ;

Hinzen, B ;

Ince, SJ ;

Ley, SV .

TETRAHEDRON-ASYMMETRY, 2000, 11 (01) :173-197

[5] MASS-SPECTROMETRIC ANALYSIS OF A GPI-ANCHORED PROTEIN - THE SCRAPIE PRION PROTEIN [J].

BALDWIN, MA ;

BURLINGAME, AL ;

PRUSINER, SB .

TRAC-TRENDS IN ANALYTICAL CHEMISTRY, 1993, 12 (06) :239-248

[6] FIRST SYNTHESIS OF A FULLY PHOSPHORYLATED GPI MEMBRANE ANCHOR - RAT-BRAIN THY-1 [J].

CAMPBELL, AS ;

FRASERREID, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (41) :10387-10388

[7]

FRASERREID B, 1992, SYNLETT, P927

[8] Structure-activity relationship of synthetic phosphoinositolglycans mimicking metabolic insulin action [J].

Frick, W ;

Bauer, A ;

Bauer, J ;

Wied, S ;

Müller, G .

BIOCHEMISTRY, 1998, 37 (38) :13421-13436

[9] RING-CLOSING METATHESIS AND RELATED PROCESSES IN ORGANIC-SYNTHESIS [J].

GRUBBS, RH ;

MILLER, SJ ;

FU, GC .

ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (11) :446-452

[10] Automated solid-phase synthesis of a branched Leishmania cap tetrasaccharide [J].

Hewitt, MC ;

Seeberger, PH .

ORGANIC LETTERS, 2001, 3 (23) :3699-3702