Block synthesis of Streptococcus pneumoniae type 14 capsular polysaccharide structures

被引：21

作者：

Sundgren, A

Lahmann, M

Oscarson, S ^{[1
]}

机构：

[1] Univ Stockholm, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden

[2] Univ Gothenburg, Dept Chem, Gothenburg, Sweden

来源：

JOURNAL OF CARBOHYDRATE CHEMISTRY | 2005年 / 24卷 / 4-6期

关键词：

oligosaccharide synthesis; block synthesis; glycoconjugate vaccines;

D O I：

10.1081/CAR-200066935

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Synthesis of a thioglycoside tetrasaccharide block, beta-D-Galp-(1 -> 4)-beta-DGlcp-(1 -> 6)-[beta-D-Galp-(1 -> 4)]-beta-D-GlcNPhthp-(1 -> SEt, corresponding to the repeating unit of Streptococcus pneumoniae serotype 14 CPS is described. Coupling of this block with a spacer followed by removal of an isopropylidene acetal yielded an acceptor, which was elongated with the donor block to give a protected dimer of the repeating unit. Iteration of this methodology yielded the trimer. Deprotection then produced an octa and a dode-casaccharide derivative ready for conjugation to proteins to afford immunoactive glycoconjugates.

引用

页码：379 / 391

页数：13

共 23 条

[11]

Kolb HC, 2001, ANGEW CHEM INT EDIT, V40, P2004, DOI 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.3.CO

[12]

2-X

[13] The synthesis of Streptococcus pneumoniae polysaccharide-tetanus toxoid conjugates and the effect of chain length on immunogenicity [J].