Automated solid-phase synthesis of a branched Leishmania cap tetrasaccharide

被引：42

作者：

Hewitt, MC ^{[1
]}

Seeberger, PH ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 23期

关键词：

D O I：

10.1021/ol016631v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Described is the first automated solid-phase synthesis of a branched oligosaccharide by stepwise assembly from monosaccharides. Cap tetrasaccharide 1, found as part of the cell surface lipophosphoglycan (LPG) of the protozoan parasite Leishmania, was readily prepared using glycosyl phosphate and glycosyl trichloroacetimidate building blocks.

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页码：3699 / 3702

页数：4

相关论文

共 21 条

[1]

AHTERTON A, 1989, SOLID PHASE PEPTIDE

[2] Leishmania and human immunodeficiency virus coinfection: The first 10 years [J].

Alvar, J ;

Canavate, C ;

GutierrezSolar, B ;

Jimenez, M ;

Laguna, F ;

LopezVelez, R ;

Molina, R ;

Moreno, J .

CLINICAL MICROBIOLOGY REVIEWS, 1997, 10 (02) :298-+

[3] 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

[4] N-pentenyl glycoside methodology in the stereoselective construction of the tetrasaccharyl cap portion of Leishmania lipophosphoglycan [J].

Arasappan, A ;

FraserReid, B .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (07) :2401-2406

[5] GENE SYNTHESIS MACHINES - DNA CHEMISTRY AND ITS USES [J].

CARUTHERS, MH .

SCIENCE, 1985, 230 (4723) :281-285

[6]

FRASERREID B, 1992, SYNLETT, P927

[7] 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

[8] Leishmaniasis [J].

Herwaldt, BL .

LANCET, 1999, 354 (9185) :1191-1199

[9] Solution and solid-support synthesis of a potential leishmaniasis carbohydrate vaccine [J].

Hewitt, MC ;

Seeberger, PH .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (12) :4233-4243

[10] Synthesis of thio-linked disaccharides by 1→2 intramolecular thioglycosyl migration:: Oxacarbenium versus episulfonium ion intermediates [J].

Johnston, BD ;

Pinto, BM .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (15) :4607-4617