Synergistic Glycosylation as Key to the Chemical Synthesis of an Outer Core Octasaccharide of Helicobacter pylori.
Chemistry
; 24(12): 2868-2872, 2018 Feb 26.
Article
in En
| MEDLINE
| ID: mdl-29319212
ABSTRACT
Helicobacter pylori, a widespread gastric bacterial pathogen that infects 90 % of the population in developing countries, causes chronic gastritis, peptic ulcers and gastric cancer. Battling H.â
pylori infection is a serious challenge due to the increased resistance to antibiotics and the lack of vaccines. The lipopolysaccharide covering the H.â
pylori cell-surface outer membrane is an attractive target for the development of a glycoconjugate vaccine. Here, we report a [3+5] convergent synthesis of an outer core octasaccharide of H.â
pylori employing just three orthogonally protected building blocks. A synergistic glycosylation strategy enables the creation of five pivotal 1,2-cis-α-glucosidic bonds consist of four types of linkages using just three monomers. This strategy can be expanded to many 1,2-cis-α-gluoside-containing oligosaccharides both in solution and solid phase.
Key words
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Oligosaccharides
/
Helicobacter pylori
/
Anti-Bacterial Agents
Type of study:
Etiology_studies
Limits:
Humans
Language:
En
Journal:
Chemistry
Journal subject:
QUIMICA
Year:
2018
Document type:
Article