Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Synthesis of the pentasaccharide repeating unit of the O-antigen of E. coli O117:K98:H4.

ABSTRACT: The pentasaccharide repeating unit of the O-antigen of E. coli O117:K98:H4 strain has been synthesized using a combination of sequential glycosylations and [3 + 2] block synthetic strategy from the suitably protected monosaccharide intermediates. Thioglycosides and glycosyl trichloroacetimidate derivatives have been used as glycosyl donors in the glycosylations.

SUBMITTER: Mandal PK

PROVIDER: S-EPMC4273275 | biostudies-literature | 2014

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Synthesis of the pentasaccharide repeating unit of the O-antigen of E. coli O117:K98:H4.

Mandal Pintu Kumar PK

Beilstein journal of organic chemistry 20141120

The pentasaccharide repeating unit of the O-antigen of E. coli O117:K98:H4 strain has been synthesized using a combination of sequential glycosylations and [3 + 2] block synthetic strategy from the suitably protected monosaccharide intermediates. Thioglycosides and glycosyl trichloroacetimidate derivatives have been used as glycosyl donors in the glycosylations. ...[more]

PMID: 25550736

Similar Datasets

Expedient Synthesis of the Pentasaccharide Repeating Unit of the Polysaccharide O-Antigen of Escherichia coli O11.

Project description:A convergent [3+2] block synthetic strategy was developed for the synthesis of the pentasaccharide repeating unit of the cell wall O-antigen of Escherichia coli O11 strain in excellent yield in a minimum number of steps. Several suitably functionalized thioglycoside derivatives were used as glycosyl donors during the synthesis of the target compound. A thioglycoside was the glycosyl donor used to couple with another thioglycoside derivative in a highly stereoselective manner exploiting the difference of their reactivity profile. A combination of Niodosuccinimide (NIS) and perchloric acid supported over silica gel (HClO4-SiO2) was used as a thiophilic glycosylation activator system in all stereoselective glycosylation reactions. HClO4-SiO2 acted as a user-friendly solid acid catalyst. Yields were very good in all glycosylation steps with a high stereoselective outcome. The synthetic pentasaccharide could be coupled to an appropriate protein to furnish a glycoconjugate derivative for its use in immunochemical studies.

| S-EPMC4906483 | biostudies-other

Convenient synthesis of the pentasaccharide repeating unit corresponding to the cell wall O-antigen of Escherichia albertii O4.

Project description:A straightforward sequential synthetic strategy has been developed for the synthesis of a pentasaccharide repeating unit corresponding to the cell wall O-antigen of the Escherichia albertii O4 strain in very good yield with the desired configuration at the glycosidic linkages using thioglycosides and trichloroacetimidate derivatives as glycosyl donors and perchloric acid supported over silica (HClO4/SiO2) as a solid supported protic acid glycosyl activator. The expected configuration at the glycosidic linkages was achieved using a reasonable selection of protecting groups in the manosaccharide intermediates.

| S-EPMC7006483 | biostudies-literature

Convergent synthesis of the pentasaccharide repeating unit of the biofilms produced by <i>Klebsiella pneumoniae</i>.

Project description:A pentasaccharide repeating unit containing α-linked D-glucuronic acid, β-linked D-mannose, corresponding to the repeating unit of biofilms produced by Klebsiella pneumoniae, has been synthesized using a stereoselective [2 + 3] convergent glycosylation strategy. The β-D-mannosidic moiety has been synthesized using a D-mannose-derived thioglycoside by a two-step activation process. Late stage TEMPO-mediated oxidation of the pentasaccharide derivative using phase-transfer reaction conditions furnished the target compound in satisfactory yield.

| S-EPMC6404407 | biostudies-literature

Straightforward synthesis of a tetrasaccharide repeating unit corresponding to the O-antigen of Escherichia coli O16.

Project description:A straightforward synthesis of the tetrasaccharide repeating unit of the O-antigen of Escherichia coli O16 has been achieved following a sequential glycosylation strategy. A minimum number of steps was used for the synthesis of the target compound involving a one-pot glycosylation and a protecting group manipulation. All intermediate reactions afford their products in high yield, and the glycosylation steps are stereoselective.

| S-EPMC3778367 | biostudies-literature

Chemical synthesis of the pentasaccharide repeating unit of the O-specific polysaccharide from Escherichia coli O132 in the form of its 2-aminoethyl glycoside.

Project description:The total chemical synthesis of the pentasaccharide repeating unit of the O-polysaccharide from E. coli O132 is accomplished in the form of its 2-aminoethyl glycoside. The 2-aminoethyl glycoside is particularly important as it allows further glycoconjugate formation utilizing the terminal amine without affecting the stereochemistry of the reducing end. The target was achieved through a [3 + 2] strategy where the required monosaccharide building blocks are prepared from commercially available sugars through rational protecting group manipulation. The NIS-mediated activation of thioglycosides was used extensively for the glycosylation reactions throughout.

| S-EPMC6839562 | biostudies-literature

Convergent synthesis of the tetrasaccharide repeating unit of the O-antigen of Shigella boydii type 9.

Project description:A convenient synthesis of the tetrasaccharide repeating unit of the O-antigen of Shigella boydii type 9 has been achieved in excellent yield using a [2 + 2] block glycosylation strategy. TEMPO-mediated selective oxidation of the primary alcohol of the tetrasaccharide derivative 8 to the carboxylic group followed by deprotection of the functional groups furnished target tetrasaccharide 1 as its 4-methoxyphenyl glycoside in high yield.

| S-EPMC3182426 | biostudies-literature

Convergent synthesis of the tetrasaccharide repeating unit of the cell wall lipopolysaccharide of Escherichia coli O40.

Project description:A tetrasaccharide repeating unit corresponding to the cell-wall lipopolysaccharide of E. coli O40 was synthesized by using a convergent block glycosylation strategy. A disaccharide donor was coupled to a disaccharide acceptor by a stereoselective glycosylation. A 2-aminoethyl linker was chosen as the anomeric protecting group at the reducing end of the tetrasaccharide. All glycosylation steps are significantly high yielding and stereoselective.

| S-EPMC3511039 | biostudies-literature

Synthesis of the Heptasaccharide Repeating Unit of the Cell Wall O-Polysaccharide of Enterotoxigenic Escherichia coli O139.

Project description:Enterotoxigenic Escherichia coli (ETEC) like the O139 strain are mostly responsible for traveler's diarrhea and causes diseases in pigs, cattle, and poultry. A convenient synthetic strategy was developed for the synthesis of the heptasaccharide repeating unit of the cell wall lipopolysaccharide of the E. coli O139 strain. The p-methoxybenzyl (PMB) group was used as a temporary protecting group which was removed in situ under the glycosylation conditions by changing the reaction temperature during the synthesis of the target compound. All glycosylation steps gave high yields with good stereoselectivity. A (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO)-mediated selective oxidation of the primary hydroxyl group was carried out using a biphasic reaction condition at the late stage of the synthesis. Such synthetic oligosaccharides could later be effectively conjugated with proteins to prepare glycoconjugate derivatives as vaccine candidates.

| S-EPMC4906484 | biostudies-literature

Synthesis of the Aeromonas veronii strain Bs8 disaccharide repeating unit.

Project description:Presented herein is the synthesis of the Aeromonas veronii disaccharide repeating unit which has been achieved in 11 steps starting from d-fucose and d-galactosamine.

| S-EPMC8983578 | biostudies-literature

Synthesis of the Staphylococcus aureus Strain M Capsular Polysaccharide Repeating Unit.

Project description:The synthesis of the Staphylococcus aureus strain M capsular polysaccharide repeating unit is reported. A postglycosylation oxidation strategy was utilized for the construction of the α-galactosaminuronic acid linkages, relying on a stereoselective 2-azido-4,6-O-di-tert-butylsilylidene galactopyranoside donor, for which the selectivity was assessed by model glycosylations. The α-fucosamine linkage was installed stereoselectively, using a reactive 2-azidofucosyl donor. An unexpected glycosidic bond cleavage during the TEMPO/PhI(OAc)2-mediated oxidation of a disaccharide intermediate was circumvented by a TEMPO/PhI(OAc)2-Pinnick oxidation protocol.

| S-EPMC5442609 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data