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Gintner M, Yoneda Y, Schmölzer C, Denner C, Kahlig H, Schmid W
A versatile de novo synthesis of legionaminic acid and 4-epi-legionaminic acid starting from D-serine
Carbohydrate Research 474(1) (2019)
34-42
Legionella pneumophila
(NCBI TaxID 446,
species name lookup)
Shewanella japonica
(NCBI TaxID 93973,
species name lookup)
Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Legionella pneumophila [ICD11:
XN9YS 
]
The structure was elucidated in this paperNCBI PubMed ID: 30711766Publication DOI: 10.1016/j.carres.2019.01.009Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: M. Gintner <manuel.gintner
univie.ac.at>
Institutions: AG Schmid, Institute of Organic Chemistry, University of Vienna, Vienna, Austria, Faculty of Agriculture, Shizuoka University, Shizuoka, Japan
Legionaminic acid and 4-epi-legionaminic acid are 5,7-diacetamido nonulosonic acids and are assumed to play a crucial role in the virulence of Legionella pneumophila, the causative agent of Legionnaires' disease. Moreover, they are ideal target motifs for the development of vaccines and pathogen detection. Herein, we present a versatile de novo synthesis of legionaminic acid and 4-epi-legionaminic acid. Starting from simple d-serine, the C9-backbone is built up by two CC-bond formation reactions. First, the protected d-serine motif is elongated utilizing a highly stereoselective nitroaldol reaction to give a C6-precursor of desired d-rhamno configuration. Second, an indium-mediated allylation is employed to further elongate the carbon backbone and introduce a masked alpha-keto acid function.
nonulosonic acid, legionaminic acid, 4-epi-Legionaminic acid, Indium-mediated allylation, Nitroaldol reaction
Structure type: monomer ; 333.1303 [M-H]-
C
13H
21N
2O
8Location inside paper: p.35, fig.1, structure 3
Trivial name: 4-epi-legionaminic acid
Compound class: nonulosonic acid
Methods: 13C NMR, 1H NMR, TLC, chemical synthesis, chemical methods, glycosylation, HR-ESI-MS
Synthetic data: chemical
Related record ID(s): 733, 734, 1016
NCBI Taxonomy refs (TaxIDs): 446,
93973Reference(s) to other database(s): GTC:G56205OY
Show glycosyltransferases
1H NMR data: present in publication
|
13C NMR data: present in publication
|
There is only one chemically distinct structure:
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Gintner M, Yoneda Y, Schmölzer C, Denner C, Kahlig H, Schmid W
A versatile de novo synthesis of legionaminic acid and 4-epi-legionaminic acid starting from D-serine
Carbohydrate Research 474(1) (2019)
34-42
Escherichia coli O108
(Ancestor NCBI TaxID 562,
species name lookup)
Morganella morganii KF1676
(Ancestor NCBI TaxID 582,
species name lookup)
Morganella morganii RK4222
(Ancestor NCBI TaxID 582,
species name lookup)
Providencia stuartii O20
(Ancestor NCBI TaxID 588,
species name lookup)
Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
NCBI PubMed ID: 30711766Publication DOI: 10.1016/j.carres.2019.01.009Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: M. Gintner <manuel.gintner
univie.ac.at>
Institutions: AG Schmid, Institute of Organic Chemistry, University of Vienna, Vienna, Austria, Faculty of Agriculture, Shizuoka University, Shizuoka, Japan
Legionaminic acid and 4-epi-legionaminic acid are 5,7-diacetamido nonulosonic acids and are assumed to play a crucial role in the virulence of Legionella pneumophila, the causative agent of Legionnaires' disease. Moreover, they are ideal target motifs for the development of vaccines and pathogen detection. Herein, we present a versatile de novo synthesis of legionaminic acid and 4-epi-legionaminic acid. Starting from simple d-serine, the C9-backbone is built up by two CC-bond formation reactions. First, the protected d-serine motif is elongated utilizing a highly stereoselective nitroaldol reaction to give a C6-precursor of desired d-rhamno configuration. Second, an indium-mediated allylation is employed to further elongate the carbon backbone and introduce a masked alpha-keto acid function.
nonulosonic acid, legionaminic acid, 4-epi-Legionaminic acid, Indium-mediated allylation, Nitroaldol reaction
Structure type: monomer
Location inside paper: p.35, fig.1, structure 4
Trivial name: 8-epi-legionaminic acid
Compound class: nonulosonic acid
Methods: 13C NMR, 1H NMR, TLC, chemical synthesis, chemical methods, glycosylation, HR-ESI-MS
Comments, role: SO from ref. 12a-12e.
Related record ID(s): 732, 734, 1016
NCBI Taxonomy refs (TaxIDs): 562,
582,
588Reference(s) to other database(s): GTC:G51313UX
Show glycosyltransferases
There is only one chemically distinct structure:
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