Found 3 structures.
Displayed structures from 1 to 3
Expand all compounds
Collapse all compounds
Show all as text (SweetDB notation)
Show all graphically (SNFG notation)
1. Compound ID: 13581
Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_130648,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_141807,IEDB_151528,IEDB_151531,IEDB_190606,SB_21,SB_7
The structure is contained in the following publication(s):
- Article ID: 5398
Arbatsky NP, Kenyon JJ, Shashkov AS, Shneider MM, Popova AV, Kalinchuk NA, Hall RM, Knirel YA "The K5 capsular polysaccharide of the bacterium Acinetobacter baumannii SDF with the same K unit containing Leg5Ac7Ac as the K7 capsular polysaccharide but a different linkage between the K units" -
Russian Chemical Bulletin = Izvestiia Akademii nauk. Seriia khimicheskaia 68(1) (2019) 163-167
The K5 capsular polysaccharide (CPS) was isolated from the bacterium Acinetobacter baumannii (A. baumannii) SDF and studied by 1D and 2D 1H and 13C NMR spectroscopy before and after O-deacetylation and partial acid hydrolysis. The CPS was found to be composed of branched tetrasaccharide repeats (K units) containing 5,7-diacetamido-3,5,7,9-tetradeoxy-d-glycero-d-galacto-non-2-ulosonic acid (Leg5Ac7Ac). The KL5 capsule biosynthesis gene cluster at the K locus is consistent with the composition and structure of the CPS. KL5 is almost identical to the KL7 gene ulosonic acid (Leg5Ac7Ac A. baumannii LUH5533 that has been characterized earlier, and differs only in the gene for Wzy polymerase that is responsible for the formation of the linkage between the K units. The K5 CPS from strain SDF and the K7 CPS from strain LUH5533 have the same K-unit structure but a different linkage between the K units, which is formed by distinct Wzy polymerases. As opposite to Leg5Ac7Ac in the K7 CPS, this monosaccharide is O-acetylated at position 4 in the K5 CPS. No acetyltransferase for this modification of the K5 CPS is present in the KL5 gene cluster, and hence it is encoded by a gene located elsewhere in the genome.
Acinetobacter baumannii, capsular polysaccharide, legionaminic acid, Wzy polymerase, gene polymorphism, KL gene locus
Publication DOI: 10.1007/s11172-019-2432-4Journal NLM ID: 100912060Publisher: New York: Consultants Bureau
Correspondence: YA Knirel
Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, School of Life and Environmental Sciences, The University of Sydney, Sydney, Australia, Institute of Health and Biomedical Innovation, School of Biomedical Sciences, Faculty of Health Queensland University of Technology, Brisbane, Australia, M. M. Shemyakin-Yu. A. Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow, Russia, Moscow Institute of Physics and Technology, 9 Institutskii per., Russian Federation, State Research Center for Applied Microbiology and Biotechnology, Obolensk, Russian Federation
Methods: 13C NMR, 1H NMR, NMR-2D, partial acid hydrolysis, sugar analysis, GLC, de-O-acetylation, bioinformatic analysis
- Article ID: 5459
Kenyon JJ, Arbatsky NP, Shneider MM, Popova AV, Dmitrenok AS, Kasimova AA, Shashkov AS, Hall RM, Knirel YA "The K46 and K5 capsular polysaccharides produced by Acinetobacter baumannii NIPH 329 and SDF have related structures and the side-chain non-ulosonic acids are acetylated by phage-encoded acetyltransferases" -
PLoS One 14(6) (2019) 0218461
Acinetobacter baumannii isolate NIPH 329 carries a novel capsular polysaccharide (CPS) gene cluster, designated KL46, that is closely related to the KL5 locus in A. baumannii isolate SDF but includes genes for synthesis of 5,7-diacetamido-3,5,7,9-tetradeoxy-l-glycero-l-manno-non-2-ulosonic (di-N-acetylpseudaminic) acid (Pse5Ac7Ac) instead of the corresponding D-glycero-D-galacto isomer (di-N-acetyllegionaminic acid) (Leg5Ac7Ac). In agreement with the genetic content of KL46, chemical studies of the K46 CPS produced by NIPH 329 revealed a branched tetrasaccharide repeat (K unit) with an overall structure the same as K5 from SDF but with β-Pse5Ac7Ac replacing α-Leg5Ac7Ac. As for K5, the K46 unit begins with d-GalpNAc and includes α-d-GlcpNAc-(1→3)-d-GalpNAc and α-d-Galp-(1→6)-d-GlcpNAc linkages, formed by Gtr14 and Gtr15 glycosyltransferases, respectively. The Gtr94K46 glycosyltransferase, which is related to Gtr13K5, links Pse5Ac7Ac to d-Galp in the growing K unit via a β-(2→6) linkage. Nearly identical Wzy enzymes connect the K46 and K5 units via a α-D-GalpNAc-(1→3)-α-D-Galp linkage to form closely related CPSs. Both Pse5Ac7Ac in K46 and Leg5Ac7Ac in K5 are acetylated at O4 but no acetyltransferase gene is present in KL46 or KL5. Related acetyltransferases were found encoded in the NIPH 329 and SDF genomes, but not in other strains carrying an unacetylated Pse or Leg derivative in the CPS. The genes encoding the acetyltransferases were in different putative phage genomes. However, related acetyltransferases were rare among the >3000 publically available genome sequences.
biosynthesis, locus, Acinetobacter baumannii, capsular polysaccharide, gene cluster, nonulosonic acid, glycosyltransferase
NCBI PubMed ID: 31220143Publication DOI: 10.1371/journal.pone.0218461Journal NLM ID: 101285081Publisher: San Francisco, CA: Public Library of Science
Correspondence: J.J. Kenyon
Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, State Research Center for Applied Microbiology and Biotechnology, Obolensk, Moscow Region, Russia, Institute of Health and Biomedical Innovation, School of Biomedical Sciences, Faculty of Health, Queensland University of Technology, Brisbane, Australia, School of Life and Environmental Sciences, The University of Sydney, Sydney, Australia, Higher Chemical College of the Russian Academy of Sciences, D. I. Mendeleev University of Chemical Technology of Russia, Moscow, Russia, M. M. Shemyakin & Y. A. Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow, Russia.4 Moscow Institute of Physics and Technology, Dolgoprudny, Moscow Region, Russia
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, GLC, mild acid hydrolysis, Smith degradation, GPC, bioinformatic analysis
- Article ID: 6254
Kasimova AA, Dudnik AG, Shashkov AS, Schneider MM, Christofferson A, Shelenkov AS, Mikhailova YV, Kenyon JJ "The K218 capsular polysaccharide produced by Acinetobacter baumannii isolate 52-249 includes 5,7-di-N-acetylpseudaminic acid linked by a KpsS3 glycosyltransferase" -
International Journal of Biological Macromolecules 218 (2022) 310-316
Two acylated forms of the higher sugar, 5,7-diamino-3,5,7,9-tetradeoxy-L-glycero-L-manno-non-2-ulosonic acid called pseudaminic acid, Pse5Ac7Ac and Pse5Ac7RHb where R indicates (R)-3-hydroxybutanoyl, have been found to occur in many capsular polysaccharide (CPS) types produced by isolates of an important human pathogen, Acinetobacter baumannii. The presence of either a psaABCEDF or psaABCGHF gene module at the K locus (KL) for CPS biosynthesis determines the type of the variant produced. Here, an A. baumannii clinical isolate 52-249, recovered in 2015 in Moscow, Russia, was found to include a novel psaABCIJF gene module in the KL218 sequence at the K locus. The CPS from 52-249 was extracted and studied by sugar analysis and partial acid hydrolysis along with one- and two-dimensional 1H and 13C NMR spectroscopy. A branched tetrasaccharide repeating unit was identified, which included a →3)-α-D-Galp-(1→6)-α-D-GlcpNAc-(1→3)-β-D-GalpNAc-(1→ main chain and Pse5Ac7Ac attached as a side branch, indicating that the psaABCIJF gene module is associated with synthesis of this variant. The K218 CPS was found to be structurally related to the K46 CPS of A. baumannii, and a comparison of the two structures enabled the assignment of glycosyltransferases. A KpsS3 protein for the α-(2→6) linkage of the Pse5Ac7Ac residue to D-Galp in K218 was identified.
Acinetobacter baumannii, capsular polysaccharide, pseudaminic acid, K locus, KpsS3
NCBI PubMed ID: 35872309Publication DOI: 10.1016/j.ijbiomac.2022.07.135Journal NLM ID: 7909578Publisher: Butterworth-Heinemann
Correspondence: J.J. Kenyon
Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, M. M. Shemyakin & Y. A. Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow, Russia, Central Scientific Research Institute of Epidemiology, Moscow, Russia, Centre for Immunology and Infection Control, School of Biomedical Sciences, Faculty of Health, Queensland University of Technology, Brisbane, Australia
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, GLC, mild acid hydrolysis, GPC, bioinformatic analysis, sequencing
Expand this compound
Collapse this compound
2. Compound ID: 13716
|
b-Psep4(75%)Ac5Ac7Ac-(2-6)-+
|
-3)-a-D-Galp-(1-6)-a-D-GlcpNAc-(1-3)-b-D-GalpNAc-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_130648,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_141807,IEDB_151528,IEDB_151531,IEDB_190606,SB_21,SB_7
The structure is contained in the following publication(s):
- Article ID: 5459
Kenyon JJ, Arbatsky NP, Shneider MM, Popova AV, Dmitrenok AS, Kasimova AA, Shashkov AS, Hall RM, Knirel YA "The K46 and K5 capsular polysaccharides produced by Acinetobacter baumannii NIPH 329 and SDF have related structures and the side-chain non-ulosonic acids are acetylated by phage-encoded acetyltransferases" -
PLoS One 14(6) (2019) 0218461
Acinetobacter baumannii isolate NIPH 329 carries a novel capsular polysaccharide (CPS) gene cluster, designated KL46, that is closely related to the KL5 locus in A. baumannii isolate SDF but includes genes for synthesis of 5,7-diacetamido-3,5,7,9-tetradeoxy-l-glycero-l-manno-non-2-ulosonic (di-N-acetylpseudaminic) acid (Pse5Ac7Ac) instead of the corresponding D-glycero-D-galacto isomer (di-N-acetyllegionaminic acid) (Leg5Ac7Ac). In agreement with the genetic content of KL46, chemical studies of the K46 CPS produced by NIPH 329 revealed a branched tetrasaccharide repeat (K unit) with an overall structure the same as K5 from SDF but with β-Pse5Ac7Ac replacing α-Leg5Ac7Ac. As for K5, the K46 unit begins with d-GalpNAc and includes α-d-GlcpNAc-(1→3)-d-GalpNAc and α-d-Galp-(1→6)-d-GlcpNAc linkages, formed by Gtr14 and Gtr15 glycosyltransferases, respectively. The Gtr94K46 glycosyltransferase, which is related to Gtr13K5, links Pse5Ac7Ac to d-Galp in the growing K unit via a β-(2→6) linkage. Nearly identical Wzy enzymes connect the K46 and K5 units via a α-D-GalpNAc-(1→3)-α-D-Galp linkage to form closely related CPSs. Both Pse5Ac7Ac in K46 and Leg5Ac7Ac in K5 are acetylated at O4 but no acetyltransferase gene is present in KL46 or KL5. Related acetyltransferases were found encoded in the NIPH 329 and SDF genomes, but not in other strains carrying an unacetylated Pse or Leg derivative in the CPS. The genes encoding the acetyltransferases were in different putative phage genomes. However, related acetyltransferases were rare among the >3000 publically available genome sequences.
biosynthesis, locus, Acinetobacter baumannii, capsular polysaccharide, gene cluster, nonulosonic acid, glycosyltransferase
NCBI PubMed ID: 31220143Publication DOI: 10.1371/journal.pone.0218461Journal NLM ID: 101285081Publisher: San Francisco, CA: Public Library of Science
Correspondence: J.J. Kenyon
Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, State Research Center for Applied Microbiology and Biotechnology, Obolensk, Moscow Region, Russia, Institute of Health and Biomedical Innovation, School of Biomedical Sciences, Faculty of Health, Queensland University of Technology, Brisbane, Australia, School of Life and Environmental Sciences, The University of Sydney, Sydney, Australia, Higher Chemical College of the Russian Academy of Sciences, D. I. Mendeleev University of Chemical Technology of Russia, Moscow, Russia, M. M. Shemyakin & Y. A. Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow, Russia.4 Moscow Institute of Physics and Technology, Dolgoprudny, Moscow Region, Russia
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, GLC, mild acid hydrolysis, Smith degradation, GPC, bioinformatic analysis
- Article ID: 6254
Kasimova AA, Dudnik AG, Shashkov AS, Schneider MM, Christofferson A, Shelenkov AS, Mikhailova YV, Kenyon JJ "The K218 capsular polysaccharide produced by Acinetobacter baumannii isolate 52-249 includes 5,7-di-N-acetylpseudaminic acid linked by a KpsS3 glycosyltransferase" -
International Journal of Biological Macromolecules 218 (2022) 310-316
Two acylated forms of the higher sugar, 5,7-diamino-3,5,7,9-tetradeoxy-L-glycero-L-manno-non-2-ulosonic acid called pseudaminic acid, Pse5Ac7Ac and Pse5Ac7RHb where R indicates (R)-3-hydroxybutanoyl, have been found to occur in many capsular polysaccharide (CPS) types produced by isolates of an important human pathogen, Acinetobacter baumannii. The presence of either a psaABCEDF or psaABCGHF gene module at the K locus (KL) for CPS biosynthesis determines the type of the variant produced. Here, an A. baumannii clinical isolate 52-249, recovered in 2015 in Moscow, Russia, was found to include a novel psaABCIJF gene module in the KL218 sequence at the K locus. The CPS from 52-249 was extracted and studied by sugar analysis and partial acid hydrolysis along with one- and two-dimensional 1H and 13C NMR spectroscopy. A branched tetrasaccharide repeating unit was identified, which included a →3)-α-D-Galp-(1→6)-α-D-GlcpNAc-(1→3)-β-D-GalpNAc-(1→ main chain and Pse5Ac7Ac attached as a side branch, indicating that the psaABCIJF gene module is associated with synthesis of this variant. The K218 CPS was found to be structurally related to the K46 CPS of A. baumannii, and a comparison of the two structures enabled the assignment of glycosyltransferases. A KpsS3 protein for the α-(2→6) linkage of the Pse5Ac7Ac residue to D-Galp in K218 was identified.
Acinetobacter baumannii, capsular polysaccharide, pseudaminic acid, K locus, KpsS3
NCBI PubMed ID: 35872309Publication DOI: 10.1016/j.ijbiomac.2022.07.135Journal NLM ID: 7909578Publisher: Butterworth-Heinemann
Correspondence: J.J. Kenyon
Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, M. M. Shemyakin & Y. A. Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow, Russia, Central Scientific Research Institute of Epidemiology, Moscow, Russia, Centre for Immunology and Infection Control, School of Biomedical Sciences, Faculty of Health, Queensland University of Technology, Brisbane, Australia
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, GLC, mild acid hydrolysis, GPC, bioinformatic analysis, sequencing
- Article ID: 6413
Knirel YA, Kasimova AA, Arbatsky NP, Shneider MM, Popova AV, Brovko FA, Shashkov AS, Senchenkova SN, Perepelov AV, Shpirt AM "5,7-Diamino-3,5,7,9-tetradeoxynon-2-ulosonic Acids in the Capsular Polysaccharides of Acinetobacter baumannii" -
Biochemistry (Moscow) 88(2) (2023) 202-210
The polysaccharide capsule surrounding bacterial cell plays an important role in pathogenesis of infections caused by the opportunistic pathogen Acinetobacter baumannii by providing protection from external factors. The structures of the capsular polysaccharide (CPS) produced by A. baumannii isolates and the corresponding CPS biosynthesis gene clusters are highly diverse, although many of them are related. Many types of A. baumannii CPSs contain isomers of 5,7-diamino-3,5,7,9-tetradeoxynon-2-ulosonic acid (DTNA). Three of these isomers, namely acinetaminic acid (l-glycero-l-altro isomer), 8-epiacinetaminic acid (d-glycero-l-altro isomer), and 8-epipseudaminic acid (d-glycero-l-manno isomer), have not been found so far in naturally occurring carbohydrates from other species. In A. baumannii CPSs, DTNAs carry N-acyl substituents at positions 5 and 7; in some CPSs, both N-acetyl and N-(3-hydroxybutanoyl) groups are present. Remarkably, pseudaminic acid carries the (R)-isomer and legionaminic acid carries the (S)-isomer of the 3-hydroxybutanoyl group. The review addresses the structure and genetics of biosynthesis of A. baumannii CPSs containing di-N-acyl derivatives of DTNA.
Acinetobacter baumannii, capsular polysaccharide, nonulosonic acid, Bacterial polysaccharide, capsule, higher monosaccharide, acyl group
NCBI PubMed ID: 37072328Publication DOI: 10.1134/S0006297923020049Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: Y.A. Knirel
Institutions: State Research Center for Applied Microbiology and Biotechnology, Obolensk, Moscow Region, 142279, Russia, Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, 117913, Russia, Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow, 117997, Russia, Branch of the Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry in Pushchino, Russian Academy of Sciences, Pushchino, Moscow Region, 142290, Russia
Expand this compound
Collapse this compound
3. Compound ID: 14645
|
b-Psep5Ac7Ac-(2-6)-+
|
-3)-a-D-Galp-(1-6)-a-D-GlcpNAc-(1-3)-b-D-GalpNAc-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_130648,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_141807,IEDB_151528,IEDB_151531,IEDB_190606,SB_21,SB_7
The structure is contained in the following publication(s):
- Article ID: 5791
Knirel YA, Van Calsteren M "Bacterial exopolysaccharides" -
Book: Comprehensive Glycoscience: From Chemistry to Systems Biology. Reference Module in Chemistry, Molecular Sciences and Chemical Engineering (2021) 1-75
Bacterial extracellular polysaccharides are known as a cell-bound capsule, a sheath, or a slime, which is excreted into the environment. They play an important role in virulence of medical bacteria and plant-to-symbiont interaction and are used for serotyping of bacteria and production of vaccines. Some exopolysaccharides have commercial applications in industry, and claims of health benefits have been documented for an increasing number of them. Exopolysaccharides have diverse composition and structure, and some contain sugar and non-sugar components that are found in bacterial carbohydrates only. The present article provides an updated collection of the data on exopolysaccharides of various classes of gram-negative and gram-positive bacteria reported until the end of 2019. When known, biosynthesis pathways of exopolysaccharides are treated in a summary manner. References are made to structure and biosynthesis relatedness between exopolysaccharides of different bacterial taxa as well as between bacterial polysaccharides and mammalian glycosaminoglycans.
polysaccharide structure, Gram-negative bacteria, capsule, Biofilm, polysaccharide biosynthesis, gram-positive bacteria, Monosaccharide composition, Bacterial exopolysaccharide, non-sugar component
Publication DOI: 10.1016/B978-0-12-819475-1.00005-5Publisher: Elsevier
Correspondence: marie-rose.vancalsteren@canada.ca; yknirel@gmail.com
Editors: Barchi J, Kamerling H
Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Saint-Hyacinthe Research and Development Centre, Agriculture and Agri-Food Canada, Saint-Hyacinthe, QC, Canada
Expand this compound
Collapse this compound
Total list of structure IDs on all result pages of the current query:
Total list of corresponding CSDB IDs (permanent record IDs):
Execution: <1 sec