Synthesis of multivalent Streptococcus suis adhesion inhibitors by enzymatic cleavage of polygalacturonic acid and 'click' conjugation

Hilbert M. Branderhorst; Raymond Kooij; Annika Salminen; Lieneke H. Jongeneel; Christopher J. Arnusch; Rob M.J. Liskamp; Jukka Finne; Roland J. Pieters

doi:10.1039/b800283e

Synthesis of multivalent Streptococcus suis adhesion inhibitors by enzymatic cleavage of polygalacturonic acid and 'click' conjugation

Hilbert M. Branderhorst, Raymond Kooij, Annika Salminen, Lieneke H. Jongeneel, Christopher J. Arnusch, Rob M.J. Liskamp, Jukka Finne, Roland J. Pieters

Research output: Contribution to journal › Article › peer-review

35 Scopus citations

Abstract

A galabiose disaccharide building block was synthesized by an efficient pectinase cleavage of polygalacturonic acid and subsequent chemical functional group transformations. Besides the disaccharide, the corresponding trisaccharide was also obtained and modified. The compounds were subsequently conjugated to dendrimers with up to eight end groups using 'click' chemistry. The compounds were evaluated as inhibitors of adhesion of the pathogen Streptococcus suis in a hemagglutination assay and strong inhibition was observed for the tetra- and octavalent galabiose compound with MIC values in the low nanomolar range. The corresponding octavalent trisaccharide was a ca. 20-fold weaker inhibitor.

Original language	English
Pages (from-to)	1425-1434
Number of pages	10
Journal	Organic and Biomolecular Chemistry
Volume	6
Issue number	8
DOIs	https://doi.org/10.1039/b800283e
State	Published - 8 Apr 2008
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1039/b800283e

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@article{f97827246fab44fe971becc1586b1a78,

title = "Synthesis of multivalent Streptococcus suis adhesion inhibitors by enzymatic cleavage of polygalacturonic acid and 'click' conjugation",

abstract = "A galabiose disaccharide building block was synthesized by an efficient pectinase cleavage of polygalacturonic acid and subsequent chemical functional group transformations. Besides the disaccharide, the corresponding trisaccharide was also obtained and modified. The compounds were subsequently conjugated to dendrimers with up to eight end groups using 'click' chemistry. The compounds were evaluated as inhibitors of adhesion of the pathogen Streptococcus suis in a hemagglutination assay and strong inhibition was observed for the tetra- and octavalent galabiose compound with MIC values in the low nanomolar range. The corresponding octavalent trisaccharide was a ca. 20-fold weaker inhibitor.",

author = "Branderhorst, {Hilbert M.} and Raymond Kooij and Annika Salminen and Jongeneel, {Lieneke H.} and Arnusch, {Christopher J.} and Liskamp, {Rob M.J.} and Jukka Finne and Pieters, {Roland J.}",

year = "2008",

month = apr,

day = "8",

doi = "10.1039/b800283e",

language = "English",

volume = "6",

pages = "1425--1434",

journal = "Organic and Biomolecular Chemistry",

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publisher = "Royal Society of Chemistry",

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TY - JOUR

T1 - Synthesis of multivalent Streptococcus suis adhesion inhibitors by enzymatic cleavage of polygalacturonic acid and 'click' conjugation

AU - Branderhorst, Hilbert M.

AU - Kooij, Raymond

AU - Salminen, Annika

AU - Jongeneel, Lieneke H.

AU - Arnusch, Christopher J.

AU - Liskamp, Rob M.J.

AU - Finne, Jukka

AU - Pieters, Roland J.

PY - 2008/4/8

Y1 - 2008/4/8

N2 - A galabiose disaccharide building block was synthesized by an efficient pectinase cleavage of polygalacturonic acid and subsequent chemical functional group transformations. Besides the disaccharide, the corresponding trisaccharide was also obtained and modified. The compounds were subsequently conjugated to dendrimers with up to eight end groups using 'click' chemistry. The compounds were evaluated as inhibitors of adhesion of the pathogen Streptococcus suis in a hemagglutination assay and strong inhibition was observed for the tetra- and octavalent galabiose compound with MIC values in the low nanomolar range. The corresponding octavalent trisaccharide was a ca. 20-fold weaker inhibitor.

AB - A galabiose disaccharide building block was synthesized by an efficient pectinase cleavage of polygalacturonic acid and subsequent chemical functional group transformations. Besides the disaccharide, the corresponding trisaccharide was also obtained and modified. The compounds were subsequently conjugated to dendrimers with up to eight end groups using 'click' chemistry. The compounds were evaluated as inhibitors of adhesion of the pathogen Streptococcus suis in a hemagglutination assay and strong inhibition was observed for the tetra- and octavalent galabiose compound with MIC values in the low nanomolar range. The corresponding octavalent trisaccharide was a ca. 20-fold weaker inhibitor.

UR - http://www.scopus.com/inward/record.url?scp=41549128450&partnerID=8YFLogxK

U2 - 10.1039/b800283e

DO - 10.1039/b800283e

M3 - Article

C2 - 18385849

AN - SCOPUS:41549128450

SN - 1477-0520

VL - 6

SP - 1425

EP - 1434

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 8

ER -

Synthesis of multivalent Streptococcus suis adhesion inhibitors by enzymatic cleavage of polygalacturonic acid and 'click' conjugation

Abstract

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