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1. (Article ID: 3817)
Arbatsky NP, Kondakova AN, Shashkov AS, Drutskaya MS, Belousov PV, Nedospasov SA, Petrova MA, Knirel YA
Structure of the O-antigen of Acinetobacter lwoffii EK30A; identification of D-homoserine, a novel non-sugar component of bacterial polysaccharides
Organic and Biomolecular Chemistry 8(15) (2010)
3571-3577
We established a peculiar structure of the O-specific polysaccharide (O-antigen) of a psychrotrophic strain of Acinetobacter lwoffii, EK30A, isolated from a 1.6-1.8 million-year-old Siberian permafrost subsoil sediment sample. The polysaccharide was released by mild acid degradation of the lipopolysaccharide and studied using chemical analyses, Smith degradation, (1)H and (13)C NMR spectroscopy and mass spectrometry. It was found to contain d-homoserine, which is N-linked to 4-amino-4,6-dideoxy-d-glucose (Qui4N) and is N-acylated itself with acetyl in about half of the repeating units or (S)-3-hydroxybutanoyl group in the other half. The following is the structure of the tetrasaccharide repeating unit of the polysaccharide: →3)-β-D-Quip4NAcyl-(1→6)-α-D-Galp-(1→4)-α-D-GalpNAc-(1→3)-α-D-FucpNAc-(1→ where Acyl stands for either N-acetyl- or N-[(S)-3-hydroxybutanoyl]-d-homoseryl.
structure, O-antigen, identification, Acinetobacter lwoffii, D-homoserine
NCBI PubMed ID: 20539880Publication DOI: 10.1039/c004090hJournal NLM ID: 101154995Publisher: The Royal Society of Chemistry
Correspondence: annakond

gmail.com
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Russian Federation, Belozersky Institute of Physico-Chemical Biology, Lomonosov Moscow State University, Moscow, Russia, Institute of Molecular Genetics, Russian Academy of Sciences, Russian Federation
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, ESI-MS, Smith degradation, mild acid degradation
The publication contains the following compound(s):
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2. (Article ID: 5411)
Casillo A, Parrilli E, Tutino ML, Corsaro MM
The outer membrane glycolipids of bacteria from cold environments: isolation, characterization, and biological activity
FEMS Microbiology Ecology 95(7) (2019)
fiz094
Lipopolysaccharides (LPSs) are the main components of the external leaflet of the outer membrane of Gram-negative bacteria. Microorganisms that colonize permanently or transiently cold habitats have evolved an array of structural adaptations, some of which involve components of bacterial membranes. These adaptations assure the perfect functionality of the membrane even at freezing or sub-freezing growth temperatures. This review summarizes the state-of-the-art information concerning the structural features of the LPSs produced by cold-adapted bacteria. The LPS structure has recently been elucidated from species mainly belonging to Gammaproteobacteria and Flavobacteriaceae. Although the reported structural heterogeneity may arise from the phylogenetic diversity of the analyzed source strains, some generalized trends can be deduced. For instance, it is clear that only a small portion of LPSs displays the O-chain. In addition, the biological activity of the lipid A portion from several cold-adapted strains is reported.
structure, lipid A, outer membrane, Cold adaptation, isolation and characterization, Rough-LPS, smooth-LPS
NCBI PubMed ID: 31210256Publication DOI: 10.1093/femsec/fiz094Journal NLM ID: 8901229Publisher: Oxford University Press
Correspondence: corsaro

unina.it
Institutions: Department of Chemical Sciences, Universitá degli Studi di Napoli Federico II, Complesso Universitario Monte S. Angelo, via Cintia, 80126 Naples, Italy
The publication contains the following compound(s):
- Compound ID: 10699
|
-3)-a-D-Quip4N-(1-4)-a-D-GlcpA-(1-6)-a-D-GlcpNAc-(1-4)-a-L-GulpNA-(1-3)-a-D-FucpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Reference(s) to other database(s): GTC:G81692NV
- Compound ID: 13605
|
?%P-8)-+ P-4)-+
| |
a-D-Manp2Ac-(1-3)-b-D-Galp-(1-4)-D-gro-a-D-manHepp-(1-5)-a-Kdop-(2-6)-b-D-GlcpN-(1-6)-b-D-GlcpN-(1-P
|
P-4)-+ |
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Structure type: oligomer
Compound class: core oligosaccharide
- Compound ID: 13615
|
R-3HOLau-(1-3)-+
|
R-3HOLau-(1-2)-+ |
| |
Lau-(1-3)-R-3HOLau-(1-3)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
| |
P-4)-+ 3HOLau-(1-2)-+ |
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Structure type: oligomer
Compound class: lipid A
- Compound ID: 2743
|
S,S-3,5HOHex-(1-4)-+
|
-4)-a-L-FucpNAc-(1-3)-a-D-QuipNAc4N-(1-2)-a-L-Rhap-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, core oligosaccharide, O-antigen
Reference(s) to other database(s): GlycomeDB:
33625
- Compound ID: 7735
|
?%a-D-GalpA-(1--P--3)--+ P-4)-+ P-4)-+
| | |
?%b-D-Fruf-(2-4)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2-6)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
|
P-3)-a-D-GalpA-(1-2)-+ |
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Structure type: oligomer
Compound class: core oligosaccharide
Reference(s) to other database(s): GlycomeDB:
36923
- Compound ID: 13602
|
/Variants 0/-D-HSer-(1-4)-+
|
-3)-b-D-Quip4N-(1-6)-a-D-Galp-(1-4)-a-D-GalpNAc-(1-3)-a-D-FucpNAc-(1-
/Variants 0/ is:
?%S-3HOBut-(1-2)-
OR (exclusively)
?%Ac-2)- |
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Structure type: polymer chemical repeating unit
Compound class: O-antigen
- Compound ID: 8824
|
b-D-GlcpNAc-(1-3)-+
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-2)-a-L-Rhap-(1-6)-a-D-Galp-(1-4)-a-D-GalpNAc-(1-3)-a-D-QuipNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Reference(s) to other database(s): GTC:G97225ZC, GlycomeDB:
37792
- Compound ID: 13606
|
?%P-3)-+ P-4)-+ P-4)-+
| | |
a-D-Galp-(1-6)-?%b-D-Galp-(1-4)-D-gro-a-D-manHepp-(1-5)-a-Kdop-(2-6)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
|
P-6)-+ |
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Structure type: oligomer
Compound class: core oligosaccharide
- Compound ID: 13616
|
R-3HOLau-(1-3)-+
|
R-3HOLau-(1-3)-+ |
| |
Lau-(1-3)-R-3HOLau-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
| |
P-4)-+ 3HOLau-(1-2)-+ |
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Structure type: oligomer
Compound class: lipid A
- Compound ID: 9514
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Reference(s) to other database(s): GTC:G30597NU
- Compound ID: 10617
|
S-3HOBut-(1-4)-+ S-3HOBut-(1-4)-+
| |
-2)-a-L-Rhap-(1-4)-a-D-GalpNAcA-(1-3)-a-D-QuipNAc4N-(1-3)-b-D-QuipNAc4N-(1- |
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Structure type: polymer chemical repeating unit
Compound class: EPS, O-polysaccharide
- Compound ID: 13604
|
D-Gro-(1--P--3)--+ P-4)-+ P-4)-+
| | |
a-Colp-(1-2)-a-D-GalpA-(1-2)-a-D-Manp-(1-5)-a-Kdop-(2-6)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P |
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Structure type: oligomer
Compound class: core oligosaccharide, LOS
- Compound ID: 13610
|
Dco-(1-2)-+
|
Pam-(1-1)-Gro-(3--P--3)--R-3HOLau-(1-3)-+
|
R-3HOLau-(1-3)-+ |
| |
Lau-(1-3)-R-3HOC14={c4}-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
| |
P-4)-+ |
|
R-3HOLau-(1-2)-+ |
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Structure type: oligomer
Compound class: lipid A
- Compound ID: 13607
|
a-Kdop-(2-?)-+
|
b-D-Glcp-(1-3)-+ | P-4)-+
| | |
a-Murp2Ac-(1-3)-a-L-Rhap-(1-3)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-a-D-Glcp-(1-5)-a-Kdop-(2-6)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
| |
b-D-Glcp-(1-6)-+ P-4)-+ |
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Structure type: oligomer
Compound class: core oligosaccharide
- Compound ID: 13617
|
Dco-(1-3)-3HOLau-(1-3)-+ 3HOLau-(1-2)-+
| |
Dco-(1-3)-/Variants 0/-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
| |
P-4)-+ 3HOLau-(1-3)-+
/Variants 0/ is:
3HOMyr-(1-2)-
OR (exclusively)
3HOLau-(1-2)- |
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Structure type: oligomer
Compound class: lipid A
- Compound ID: 8441
|
2HOLau-(1-3)-3HOLau-(1-2)-+
|
3HODco-(1-3)-+ |
| |
Lau-(1-3)-3HOLau-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
| |
P-4)-+ 3HODco-(1-3)-+ |
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Structure type: oligomer
Compound class: lipid A
- Compound ID: 10622
|
b-L-ArapNAc3NAc4NAc-(1-4)-b-D-GlcpNAc3NAcA6NH2-(1-3)-a-L-Rhap-(1-2)-a-L-Rhap-(1-4)-+
|
-3)-b-D-QuipNAc4NAc-(1-3)-a-D-Galp-(1-
AraN3N4N = 2,3,4-triamino-2,3,4-trideoxy-L-arabinose |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
- Compound ID: 10620
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
- Compound ID: 13609
|
a-D-Glcp-(1-2)-b-D-Glcp-(1-6)-+ EtN-(1---P---P---4)-+ P-4)-+
| | |
a-D-Glcp-(1-2)-L-gro-a-D-manHepp-(1-7)-D-gro-a-D-manHepp-(1-5)-a-Kdop8N-(2-6)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
|
L-gro-a-D-manHepp-(1-2)-+ |
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Structure type: oligomer
Compound class: core oligosaccharide
- Compound ID: 13611
|
R-3HOMyr-(1-3)-+
|
R-3HOMyr-(1-3)-+ |
| |
Dco-(1-3)-Subst-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
| |
P-4)-+ Subst-(1-2)-+
Subst = (R)-3-hydroxy-undecanoic acid = SMILES CCCCCCCC{3}[C@@H](O)C{1}C(O)=O |
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Structure type: oligomer
Compound class: lipid A
- Compound ID: 13612
|
R-3HOMyr-(1-3)-+
|
R-3HOMyr-(1-3)-+ |
| |
Lau-(1-3)-Subst-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
| |
P-4)-+ Subst-(1-2)-+
Subst = (R)-3-hydroxy-undecanoic acid = SMILES CCCCCCCC{3}[C@@H](O)C{1}C(O)=O |
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Structure type: oligomer
Compound class: lipid A
- Compound ID: 13613
|
C12={5}-(1-3)-R-3HODco-(1-2)-+
|
P-4)-+ |
| |
3HODco-(1-3)-R-3HODco-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
|
3HODco-(1-3)-+ |
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Structure type: oligomer
Compound class: lipid A
- Compound ID: 13614
|
Lau-(1-3)-R-3HODco-(1-2)-+
|
P-4)-+ |
| |
3HODco-(1-3)-R-3HODco-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
|
R-3HODco-(1-3)-+ |
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Structure type: oligomer
Compound class: lipid A
- Compound ID: 13618
|
Lau-(1-3)-3HOMyr-(1-3)-+ 3HOMyr-(1-2)-+
| |
Subst-(1-3)-3HOMyr-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
| |
P-4)-+ 3HOMyr-(1-3)-+
Subst = 5,8-tetradecadienoic acid = SMILES CCCCCC=CCC=CCCCC{1}(O)=O |
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Structure type: oligomer
Compound class: lipid A
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