Prevotella denticola Lipopolysaccharide from a Cystic Fibrosis Isolate Possesses a Unique Chemical Structure

Flaviana Di Lorenzo; Alba Silipo; Thomas Matier; Anna Hanuszkiewicz; J. Stuart Elborn; Rosa Lanzetta; Luisa Sturiale; Andrea Scamporrino; Domenico Garozzo; Miguel A. Valvano; Michael M. Tunney; Antonio Molinaro

doi:10.1002/ejoc.201600037

Prevotella denticola Lipopolysaccharide from a Cystic Fibrosis Isolate Possesses a Unique Chemical Structure

Flaviana Di Lorenzo^*, Alba Silipo, Thomas Matier, Anna Hanuszkiewicz, J. Stuart Elborn, Rosa Lanzetta, Luisa Sturiale, Andrea Scamporrino, Domenico Garozzo, Miguel A. Valvano, Michael M. Tunney, Antonio Molinaro

^*Corresponding author for this work

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

11 Citations (Scopus)

Abstract

We report the first complete structural characterization of the lipopolysaccharide (LPS) from a cystic fibrosis (CF) clinical isolate of Prevotella denticola (B003V1S1X). Chemical, spectroscopic, and spectrometric analyses revealed a unique rough-type LPS (LOS) structure. The structure has a highly negatively charged heptasaccharide core region containing hexoses, with the first two sugars, 3-deoxy-D-manno-oct-2-ulosonic acid (Kdo) and mannose, highly phosphorylated. Furthermore, the lipid A moiety has the typical structure for the genus Prevotella, and was also highly phosphorylated.

Original language	English
Pages (from-to)	1732-1738
Number of pages	7
Journal	European Journal of Organic Chemistry
Volume	2016
Issue number	9
Early online date	29 Feb 2016
DOIs	https://doi.org/10.1002/ejoc.201600037
Publication status	Published - 23 Mar 2016

Keywords

Bacteria
Carbohydrates
NMR spectroscopy
Oligosaccharides
Structure elucidation

ASJC Scopus subject areas

Organic Chemistry
Physical and Theoretical Chemistry

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10.1002/ejoc.201600037

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Di Lorenzo, F., Silipo, A., Matier, T., Hanuszkiewicz, A., Elborn, J. S., Lanzetta, R., Sturiale, L., Scamporrino, A., Garozzo, D., Valvano, M. A., Tunney, M. M., & Molinaro, A. (2016). Prevotella denticola Lipopolysaccharide from a Cystic Fibrosis Isolate Possesses a Unique Chemical Structure. European Journal of Organic Chemistry, 2016(9), 1732-1738. https://doi.org/10.1002/ejoc.201600037

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title = "Prevotella denticola Lipopolysaccharide from a Cystic Fibrosis Isolate Possesses a Unique Chemical Structure",

abstract = "We report the first complete structural characterization of the lipopolysaccharide (LPS) from a cystic fibrosis (CF) clinical isolate of Prevotella denticola (B003V1S1X). Chemical, spectroscopic, and spectrometric analyses revealed a unique rough-type LPS (LOS) structure. The structure has a highly negatively charged heptasaccharide core region containing hexoses, with the first two sugars, 3-deoxy-D-manno-oct-2-ulosonic acid (Kdo) and mannose, highly phosphorylated. Furthermore, the lipid A moiety has the typical structure for the genus Prevotella, and was also highly phosphorylated.",

keywords = "Bacteria, Carbohydrates, NMR spectroscopy, Oligosaccharides, Structure elucidation",

author = "{Di Lorenzo}, Flaviana and Alba Silipo and Thomas Matier and Anna Hanuszkiewicz and Elborn, {J. Stuart} and Rosa Lanzetta and Luisa Sturiale and Andrea Scamporrino and Domenico Garozzo and Valvano, {Miguel A.} and Tunney, {Michael M.} and Antonio Molinaro",

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doi = "10.1002/ejoc.201600037",

language = "English",

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Di Lorenzo, F, Silipo, A, Matier, T, Hanuszkiewicz, A, Elborn, JS, Lanzetta, R, Sturiale, L, Scamporrino, A, Garozzo, D, Valvano, MA , Tunney, MM & Molinaro, A 2016, 'Prevotella denticola Lipopolysaccharide from a Cystic Fibrosis Isolate Possesses a Unique Chemical Structure', European Journal of Organic Chemistry, vol. 2016, no. 9, pp. 1732-1738. https://doi.org/10.1002/ejoc.201600037

TY - JOUR

T1 - Prevotella denticola Lipopolysaccharide from a Cystic Fibrosis Isolate Possesses a Unique Chemical Structure

AU - Di Lorenzo, Flaviana

AU - Silipo, Alba

AU - Matier, Thomas

AU - Hanuszkiewicz, Anna

AU - Elborn, J. Stuart

AU - Lanzetta, Rosa

AU - Sturiale, Luisa

AU - Scamporrino, Andrea

AU - Garozzo, Domenico

AU - Valvano, Miguel A.

AU - Tunney, Michael M.

AU - Molinaro, Antonio

PY - 2016/3/23

Y1 - 2016/3/23

N2 - We report the first complete structural characterization of the lipopolysaccharide (LPS) from a cystic fibrosis (CF) clinical isolate of Prevotella denticola (B003V1S1X). Chemical, spectroscopic, and spectrometric analyses revealed a unique rough-type LPS (LOS) structure. The structure has a highly negatively charged heptasaccharide core region containing hexoses, with the first two sugars, 3-deoxy-D-manno-oct-2-ulosonic acid (Kdo) and mannose, highly phosphorylated. Furthermore, the lipid A moiety has the typical structure for the genus Prevotella, and was also highly phosphorylated.

AB - We report the first complete structural characterization of the lipopolysaccharide (LPS) from a cystic fibrosis (CF) clinical isolate of Prevotella denticola (B003V1S1X). Chemical, spectroscopic, and spectrometric analyses revealed a unique rough-type LPS (LOS) structure. The structure has a highly negatively charged heptasaccharide core region containing hexoses, with the first two sugars, 3-deoxy-D-manno-oct-2-ulosonic acid (Kdo) and mannose, highly phosphorylated. Furthermore, the lipid A moiety has the typical structure for the genus Prevotella, and was also highly phosphorylated.

KW - Bacteria

KW - Carbohydrates

KW - NMR spectroscopy

KW - Oligosaccharides

KW - Structure elucidation

UR - http://www.scopus.com/inward/record.url?scp=84959257307&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201600037

DO - 10.1002/ejoc.201600037

M3 - Article

AN - SCOPUS:84959257307

SN - 1434-193X

VL - 2016

SP - 1732

EP - 1738

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 9

ER -

Prevotella denticola Lipopolysaccharide from a Cystic Fibrosis Isolate Possesses a Unique Chemical Structure

Abstract

Keywords

ASJC Scopus subject areas

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