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1. (Article ID: 6312)
Shashkov AS, Arbatsky NP, Senchenkova SN, Perepelov AV, Chizhov AO, Dmitrenok AS, Shneider MM, Knirel YA
NoteIdentification of 5,7-diacetamido-3,5,7,9-tetradeoxy-d-glycero-l-manno-non-2-ulosonic acid (di-N-acetyl-8-epipseudaminic acid) in the capsular polysaccharide of Acinetobacter baumannii Res546
Carbohydrate Research 513 (2022)
108531
A structurally diverse capsular polysaccharide that surrounds the bacterial cell plays an important role in virulence of Acinetobacter baumannii, a cause of nosocomial infections worldwide. Various isomers of 5,7-diacylamido-3,5,7,9-tetradeoxynon-2-ulosonic acid have been identified as components of bacterial polysaccharides. In this work, we report on the identification of a new isomer having the d-glycero-l-manno configuration (8-epipseudaminic acid) in the capsular polysaccharide of A. baumannii Res546. The higher sugar was isolated by Smith degradation of the polysaccharide followed by mild acid hydrolysis and identified by a comparison with all isomers using NMR spectroscopy and optical rotation.
Acinetobacter baumannii, capsular polysaccharide, 5, 7, 9-tetradeoxynon-2-ulosonic acid, 7-diacetamido-3, higher monosaccharide
NCBI PubMed ID: 35245711Publication DOI: 10.1016/j.carres.2022.108531Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: A.S. Shashkov
mail.ru>
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
Methods: 13C NMR, 1H NMR, NMR-2D, mild acid hydrolysis, Smith degradation, GPC, optical rotation measurement, NaBH4 reduction, HR-ESI-MS, cultivation
The publication contains the following compound(s):
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2. (Article ID: 6313)
Shashkov AS, Kasimova AA, Arbatsky NP, Senchenkova SN, Perepelov AV, Dmitrenok AS, Chizhov AO, Knirel YA, Kenyon JJ
Complete chemical structure of the K135 capsular polysaccharide produced by Acinetobacter baumannii RES-546 that contains 5,7-di-N-acetyl-8-epipseudaminic acid
Carbohydrate Research 523 (2023)
108726
A structurally diverse capsular polysaccharide (CPS) in the outer cell envelope plays an important role in the virulence of the important bacterial pathogen, Acinetobacter baumannii. More than 75 different CPS structures have been determined for the species to date, and many CPSs include isomers of a higher sugar, namely 5,7-diamino-3,5,7,9-tetradeoxynon-2-ulosonic acid. Recently, a novel isomer having the D-glycero-L-manno configuration (5,7-di-N-acetyl-8-epipseudaminic acid; 8ePse5Ac7Ac) has been identified in the CPS from A. baumannii clinical isolate RES-546 [Carbohydr. Res. 513 (2022) 108,531]. Here, the complete chemical structure of this CPS, designated K135, was elucidated. The CPS was found to have a branched tetrasaccharide K unit and to include the higher sugar as part of a 8ePse5Ac7Ac-(2→6)-α-Gal disaccharide branching from a →3)-α-D-GlcpNAc-(1→3)-β-D-GlcpNAc-(1→ main chain. Assignment of glycosyltransferases encoded by the CPS biosynthesis gene cluster in the RES-546 genome enabled the first sugar of the K unit, and hence the topology of the K135 CPS, to be determined.
Acinetobacter baumannii, capsular polysaccharide, 5, 7, 9-tetradeoxynon-2-ulosonic acid, 7-diacetamido-3, K135
NCBI PubMed ID: 36446189Publication DOI: 10.1016/j.carres.2022.108726Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: J.J. Kenyon
qut.edu.au>
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Centre for Immunology and Infection Control, School of Biomedical Sciences, Faculty of Health, Queensland University of Technology, Brisbane, Australia, State Research Center for Applied Microbiology and Biotechnology, Obolensk, Moscow, Region, Russia, M.M. Shemyakin & Y. A Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow, Russia
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, acid hydrolysis, GLC, Smith degradation, GPC, bioinformatic analysis
The publication contains the following compound(s):
- Compound ID: 16288
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b-8ePsep5Ac7Ac-(2-6)-a-D-Galp-(1-6)-+
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-3)-a-D-GlcpNAc-(1-3)-b-D-GlcpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS
- Compound ID: 16289
Structure type: polymer chemical repeating unit
Compound class: CPS
- Compound ID: 16290
Structure type: oligomer
Compound class: CPS
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3. (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
gmail.com>
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
The publication contains the following compound(s):
- Compound ID: 11621
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a-Psep5Ac7Ac-(2-6)-b-D-Glcp-(1-6)-+
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-3)-b-D-Galp-(1-3)-b-D-GalpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS, polysaccharide
Reference(s) to other database(s): GTC:G97931NE, GenDB:JX976549.1
- Compound ID: 14642
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a-D-GlcpNAc-(1-3)-+
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/Variants 0/-a-Legp5Ac-(2-6)-+ |
| |
-4)-b-D-Galp-(1-6)-b-D-Galp-(1-3)-b-D-GalpNAc-(1-
/Variants 0/ is:
71%S-3HOBut-(1-7)-
OR (exclusively)
29%Ac-7)- |
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Structure type: polymer chemical repeating unit
Compound class: CPS
- Compound ID: 12021
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a-Legp5Ac7Ac-(2-6)-a-D-Galp-(1-6)-+
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-3)-a-D-GlcpNAc-(1-3)-b-D-GalpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS
Reference(s) to other database(s): GTC:G59392AM
- Compound ID: 13579
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a-Legp4Ac5Ac7Ac-(2-6)-+
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-3)-a-D-Galp-(1-6)-a-D-GlcpNAc-(1-3)-b-D-GalpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS
Reference(s) to other database(s): GTC:G78472HA
- Compound ID: 13716
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b-Psep4(75%)Ac5Ac7Ac-(2-6)-+
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-3)-a-D-Galp-(1-6)-a-D-GlcpNAc-(1-3)-b-D-GalpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS
Reference(s) to other database(s): GTC:G90220UD
- Compound ID: 13914
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b-Psep5Ac7Ac-(2-3)-a-D-Galp-(1-6)-+
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-3)-a-D-GlcpNAc-(1-3)-b-D-GlcpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS
Reference(s) to other database(s): GTC:G72625RM
- Compound ID: 12581
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a-Acip5Ac7Ac-(2-6)-+
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-4)-a-D-Galp-(1-3)-a-L-FucpNAc-(1-3)-a-D-FucpNAc-(1- |
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Structure type: polymer chemical repeating unit
Trivial name: K13 CPS
Compound class: CPS
Reference(s) to other database(s): GTC:G01535IF
- Compound ID: 12571
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R-3HOBut-(1-7)-b-Psep5Ac-(2-6)-a-D-Galp-(1-6)-+
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-3)-b-D-Galp-(1-3)-b-D-GalpNAc-(1- |
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Structure type: polymer chemical repeating unit
-
Trivial name: K93 CPS
Compound class: CPS
- Compound ID: 12014
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R-3HOBut-(1-7)-a-Psep5Ac-(2-4)-+
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-3)-b-D-Ribp-(1-3)-b-D-GalpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS
- Compound ID: 12255
Structure type: polymer chemical repeating unit
Compound class: CPS
Reference(s) to other database(s): GTC:G41500KK
- Compound ID: 11852
Structure type: polymer chemical repeating unit
Compound class: CPS, cell wall polysaccharide
Reference(s) to other database(s): GTC:G73006WP
- Compound ID: 13576
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a-Legp5Ac7Ac-(2-6)-+
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-4)-a-D-GalpNAc-(1-3)-a-L-FucpNAc-(1-3)-b-D-GlcpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS
Reference(s) to other database(s): GTC:G60315IO
- Compound ID: 16529
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/Variants 0/-a-Legp5Ac-(2-6)-+
|
-3)-a-D-GalpNAc-(1-3)-a-L-FucpNAc-(1-3)-b-D-GlcpNAc-(1-
/Variants 0/ is:
71%S-3HOBut-(1-7)-
OR (exclusively)
29%Ac-7)- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: CPS
- Compound ID: 12583
|
a-Acip5Ac7Ac-(2-6)-+
|
-3)-a-D-GalpNAc-(1-3)-a-L-FucpNAc-(1-3)-a-D-FucpNAc-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Trivial name: K12 CPS
Compound class: CPS
Reference(s) to other database(s): GTC:G90675WE
- Compound ID: 12582
|
a-8eAcip5Ac7Ac-(2-6)-+
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-4)-a-D-Galp-(1-3)-a-L-FucpNAc-(1-3)-a-D-FucpNAc-(1- |
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Structure type: polymer chemical repeating unit
Trivial name: K73 CPS
Compound class: CPS
Reference(s) to other database(s): GTC:G69727CP
- Compound ID: 11927
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-4)-b-Psep5Ac7Ac-(2-6)-b-D-Galp-(1-6)-b-D-Galp-(1-3)-a-D-GalpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS
Reference(s) to other database(s): GTC:G18298UG
- Compound ID: 16156
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a-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
- Compound ID: 16288
|
b-8ePsep5Ac7Ac-(2-6)-a-D-Galp-(1-6)-+
|
-3)-a-D-GlcpNAc-(1-3)-b-D-GlcpNAc-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: CPS
- Compound ID: 13712
Structure type: polymer chemical repeating unit
Compound class: CPS
Reference(s) to other database(s): GTC:G68901CU
- Compound ID: 16530
|
/Variants 0/-+ a-D-GlcpNAc-(1-3)-+
| |
-4)-a-Legp5Ac-(2-6)-b-D-Galp-(1-6)-b-D-Galp-(1-3)-b-D-GalpNAc-(1-
/Variants 0/ is:
71%S-3HOBut-(1-7)-
OR (exclusively)
29%Ac-7)- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: CPS
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