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1. (Article ID: 4359)
Nazarenko EL, Crawford RJ, Ivanova EP
The structural diversity of carbohydrate antigens of selected Gram-negative marine bacteria
Marine Drugs 9(10) (2011)
1914-1954
Marine microorganisms have evolved for millions of years to survive in the environments characterized by one or more extreme physical or chemical parameters, e.g., high pressure, low temperature or high salinity. Marine bacteria have the ability to produce a range of biologically active molecules, such as antibiotics, toxins and antitoxins, antitumor and antimicrobial agents, and as a result, they have been a topic of research interest for many years. Among these biologically active molecules, the carbohydrate antigens, lipopolysaccharides (LPSs, O-antigens) found in cell walls of gram-negative marine bacteria, show great potential as candidates in the development of drugs to prevent septic shock due to their low virulence. The structural diversity of LPSs is thought to be a reflection of the ability for these bacteria to adapt to an array of habitats, protecting the cell from being compromised by exposure to harsh environmental stress factors. Over the last few years, the variety of structures of core oligosaccharides and O-specific polysaccharides from LPSs of marine microrganisms has been discovered. In this review, we discuss the most recently encountered structures that have been identified from bacteria belonging to the genera Aeromonas, Alteromonas, Idiomarina, Microbulbifer, Pseudoalteromonas, Plesiomonas and Shewanella of the Gammaproteobacteria phylum; Sulfitobacter and Loktanella of the Alphaproteobacteria phylum and to the genera Arenibacter, Cellulophaga, Chryseobacterium, Flavobacterium, Flexibacter of the Cytophaga-Flavobacterium-Bacteroides phylum. Particular attention is paid to the particular chemical features of the LPSs, such as the monosaccharide type, non-sugar substituents and phosphate groups, together with some of the typifying traits of LPSs obtained from marine bacteria. A possible correlation is then made between such features and the environmental adaptations undertaken by marine bacteria.
O-specific polysaccharides, carbohydrate antigens, marine microorganisms
NCBI PubMed ID: 22073003Publication DOI: 10.3390/md9101914Journal NLM ID: 101213729Publisher: Basel, Switzerland: Molecular Diversity Preservation International
Correspondence: elnaz

piboc.dvo.ru
Institutions: Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Vladivostok 690022, Russia, Faculty of Life and Social Sciences, Swinburne University of Technology, PO Box 218, Hawthorn, Victoria 3122, Australia
Methods: 13C NMR, 1H NMR, methylation, periodate oxidation, NMR-2D, FAB-MS, partial acid hydrolysis, NMR, HF solvolysis, sugar analysis, 31P NMR, ESI-MS, acid hydrolysis, mild acid hydrolysis, HPAEC, ESI-ICR-MS, Smith degradation, chemical methods, MALDI-TOF MS, MS, de-O-acetylation, NMR-1D, GPC, alkaline hydrolysis, CE-ESI-MS, CE-MS, hydrazinolysis
The publication contains the following compound(s):
- Compound ID: 267
|
-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1-2)-a-D-Galp-(1-3)-a-D-GlcpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Reference(s) to other database(s): GTC:G76746EO, GlycomeDB:
6223
- Compound ID: 10602
|
S-2HOBut-(1-7)-+
|
-4)-b-Sugp5Ac-(2-2)-S-2HOGlt-(5-4)-b-D-QuipNAc4N3Ac-(1-
Sug = 5,7,8-triamino-3,5,7,8,9-pentadeoxy-?-glycero-L-manno-non-2-ulosonic acid = SMILES CC({7}[C@@H]([C@@H]1O{2}[C@@](C(O)=O)(C{4}[C@@H]({5}[C@@H]1N)O)O)N)N |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
- Compound ID: 10601
|
-4)-b-D-GlcpNAcA3Ac-(1-4)-a-L-FucpNAm3Ac-(1-3)-a-D-6dxylHexpNAc-4-ulo-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
- Compound ID: 791
|
-2)-a-L-Rhap-(1-2)-a-L-Rhap-(1-3)-a-L-Rhap-(1-3)-b-D-GlcpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen, Shigella serogroup Y antigen, rhamnoglucan
Reference(s) to other database(s): GTC:G98477AV, GlycomeDB:
3543, CCSD:
2501, CBank-STR:8288, GenDB:AFl28887
- Compound ID: 10691
|
P-6:4)-+
|
a-Colp-(1-2)-b-D-Galp-(1-3)-+
|
-6)-b-D-GlcpNAc-(1-4)-a-D-GalpA-(1-3)-b-D-QuipNAc-(1-
|
a-Colp-(1-4)-+ |
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Structure type: polymer biological repeating unit
Compound class: CPS
Reference(s) to other database(s): GTC:G04818MQ
- Compound ID: 10696
|
a-Colp-(1-4)-+
|
P-6:4)-+ |
| |
a-Colp-(1-2)-b-D-Galp-(1-3)-b-D-GlcpNAc |
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Structure type: fragment of a bigger structure
Reference(s) to other database(s): GTC:G76596AH
- Compound ID: 10679
|
Subst-(1-3)-+
|
L-gro-a-D-manHepp-(1-7)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdo
Subst = outer core |
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Structure type: oligomer
Compound class: core oligosaccharide
- Compound ID: 1411
|
L-Ala2Ac-(1-3)-+
|
-3)-a-D-GalpNAcA-(1-3)-b-D-QuipNAc-(1-4)-b-D-Quip3N-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS
- Compound ID: 1653
|
b-D-Glcp-(1-4)-+ a-D-Manp-(1-4)-+
| |
-3)-a-D-Manp6(70%)Ac-(1-3)-b-D-Xylp-(1-3)-a-D-GlcpA-(1- |
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Structure type: polymer chemical repeating unit
Trivial name: aeromonas gum
Compound class: EPS
Reference(s) to other database(s): GTC:G75814UB
- Compound ID: 1654
Structure type: polymer chemical repeating unit
Trivial name: aeromonas gum
Compound class: EPS
Reference(s) to other database(s): GTC:G55533YN, GlycomeDB:
27479
- Compound ID: 10688
|
a-D-GlcpN-(1-7)-L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-+
|
50%b-D-Galp-(1-4)-+ | P-4)-+
| | |
D-gro-a-D-manHepp-(1-6)-D-gro-a-D-manHepp-(1-6)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/
|
L-gro-a-D-manHepp-(1-6)-+ |
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Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
Reference(s) to other database(s): GTC:G10509UC
- 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: 10700
|
a-D-Quip4N-(1-4)-a-D-GlcpA-(1-6)-a-D-GlcpNAc-(1-4)-a-L-GulpNA-(1-3)-a-D-FucpNAc |
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Structure type: oligomer
Compound class: O-polysaccharide
Reference(s) to other database(s): GTC:G37239IR
- Compound ID: 10674
|
-2)-a-L-Rhap-(1-2)-a-L-Rhap-(1-4)-b-D-GalpA-(1-3)-b-D-GalpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Reference(s) to other database(s): GTC:G45855SV
- Compound ID: 2492
|
-3)-b-D-Galp-(1-3)-b-D-GlcpNAc-(1-4)-a-L-Rhap-(1-3)-a-D-GalpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS, O-polysaccharide
Reference(s) to other database(s): GTC:G61592HT, GlycomeDB:
25811
- Compound ID: 10693
|
a-Colp-(1-4)-+
|
a-Colp-(1-2)-+ |
| |
-3)-b-D-Galp-(1-3)-b-D-GlcpNAc-(1-4)-a-L-Rhap-(1-3)-a-D-GalpNAc-(1- |
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Structure type: polymer biological repeating unit
Compound class: CPS
Reference(s) to other database(s): GTC:G93056DK
- Compound ID: 10698
Structure type: fragment of a bigger structure
Reference(s) to other database(s): GTC:G00050ID
- Compound ID: 2539
|
a-L-6dTalp?(%)Ac-(1-3)-+
|
-3)-b-D-GalpNAc-(1-4)-a-D-Manp-(1-3)-a-L-6dTalp2Ac-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Reference(s) to other database(s): GTC:G92642PY, GlycomeDB:
25754
- Compound ID: 2713
|
-4)-a-D-GalpA-(1-3)-a-D-GlcpNAc-(1-3)-a-L-Rhap-(1-2)-a-L-Rhap-(1-2)-a-L-Rhap-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Reference(s) to other database(s): GTC:G79901CF, GlycomeDB:
25907
- Compound ID: 2715
|
a-L-Rhap-(1-3)-+
|
-6)-b-D-ManpNAc-(1-4)-b-D-GlcpA-(1-3)-b-D-GalpNAc-(1-
|
b-D-Galp-(1-4)-+ |
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Structure type: polymer chemical repeating unit
Trivial name: side-chain polysaccharide
Compound class: O-polysaccharide
Reference(s) to other database(s): GTC:G10019QJ, GlycomeDB:
26518
- 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: 10683
|
90%3HOBut-(1-4)-a-D-Quip4N-(1-4)-a-D-GlcpA-(1-3)-+
|
-4)-b-D-Manp-(1-4)-b-D-Glcp-(1-3)-b-D-GlcpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS
- Compound ID: 7524
|
2HOSuc2(70%)Ac-(4-3)-+
|
-4)-a-L-GalpNAmA3Ac-(1-3)-a-D-6dxylHexpNAc-4-ulo-(1-4)-b-D-GlcpNAc3NA-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
- Compound ID: 5049
|
a-D-Glcp-(1-4)-+
|
b-L-Quip3NAc-(1-3)-a-D-Galp-(1-3)-L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp
|
a-D-Glcp-(1-6)-+ |
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Structure type: oligomer
Compound class: core oligosaccharide, LPS
Reference(s) to other database(s): GTC:G39606MO, GlycomeDB:
28344
- Compound ID: 10689
|
a-D-GlcpN-(1-7)-L-gro-b-D-manHepp-(1-4)-+
|
a-D-Glcp-(1-4)-a-D-GalpNAc-(1-6)-a-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-6)-Kdof
|
L-gro-a-D-manHepp-(1-6)-+ |
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Structure type: oligomer
Compound class: core oligosaccharide
Reference(s) to other database(s): GTC:G26637SV
- Compound ID: 10690
|
a-D-GalpNAc-(1-7)-L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-?)-+ P-4)-+
| |
/Variants 0/-L-gro-a-D-manHepp-(1-6)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/
|
L-gro-a-D-manHepp-(1-6)-+
/Variants 0/ is:
a-D-Galp-(1-4)-b-D-GalpNAc-(1-4)-
OR (exclusively)
a-D-Galp-(1-4)- |
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Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
- Compound ID: 10667
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Reference(s) to other database(s): GTC:G12363UF
- Compound ID: 7528
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Reference(s) to other database(s): GTC:G11688BP, GlycomeDB:
34668
- Compound ID: 10680
|
a-D-GalpN-(1-4)-a-D-GalpA-(1-7)-L-gro-a-D-manHepp-(1-7)-+ b-D-Galp-(1-4)-+
| |
a-L-AltpNAcA-(1-3)-b-D-FucpNAc4N-(1-4)-b-D-GlcpNAc-(1-6)-a-D-GlcpN-(1-4)-a-D-GalpA-(1-3)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdo
|
b-D-Glcp-(1-2)-+ |
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Structure type: oligomer
Compound class: core oligosaccharide
Reference(s) to other database(s): GTC:G48631IA
- Compound ID: 10684
|
a-D-GalpA-(1--P--4)--+
|
b-D-Fruf-(2-6)-a-D-Galp-(1-6)-a-D-Galp-(1-3)-a-D-Galp-(1--P--3)--D-gro-a-D-manHepp-(1-5)-a-Kdop8N-(2--/lipid A/ |
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Structure type: oligomer
Aglycon: lipid A
Compound class: CPS
Reference(s) to other database(s): GTC:G58292UI
- Compound ID: 10685
|
?%P0NH2-(0-3)-+ a-D-GalpA-(1--P--4)--+
| |
EtN-(1--P--0)--?%P-2)-D-gro-a-D-manHepp-(1-5)-a-Kdop8N-(2--/lipid A/ |
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Structure type: oligomer
Aglycon: lipid A
Compound class: CPS
- Compound ID: 8153
|
D-Gro-(1--P--3)--+
|
-3)-b-D-GalpNAc-(1-4)-b-D-GalpNAc-(1-4)-b-D-GlcpNAc-(1-4)-a-L-Rhap-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Reference(s) to other database(s): GTC:G06480TM
- Compound ID: 10671
|
2HOSuc-(4-2)-+
|
-4)-a-L-Galp?Ac-(1-3)-a-D-6dxylHexpNAc-4-ulo-(1-4)-b-L-GlcpNA-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
- Compound ID: 10672
|
R-2HOSuc2(70%)Ac-(4-3)-+
|
-4)-b-D-GlcpNAc3NA6NH2-(1-4)-a-L-GalpNAmA-(1-3)-a-D-QuipNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
- Compound ID: 10675
|
b-D-Galf-(1-4)-a-L-Rhap-(1-3)-+
|
-4)-D-gro-b-D-manHepp-(1-3)-b-D-6dmanHepp?Ac-(1-4)-a-L-Rhap-(1-3)-b-D-GlcpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Reference(s) to other database(s): GTC:G82300BS
- Compound ID: 10678
|
b-D-Glcp-(1-6)-+ L-gro-a-D-manHepp-(1-7)-+ b-D-Galp-(1-4)-+
| | |
b-D-Galp-(1-4)-a-D-GlcpN-(1-4)-a-D-GalpA-(1-3)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdo
|
b-D-Glcp-(1-2)-+ |
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Structure type: oligomer
Compound class: core oligosaccharide
Reference(s) to other database(s): GTC:G07673LH
- Compound ID: 8957
|
a-Neup-(2-8)-+
|
a-Kdop-(2-4)-a-Kdop-(2-6)-b-D-GlcpN-(1-6)-b-D-GlcpN-(1-1)-a-D-GalpA |
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Structure type: oligomer
Trivial name: core region of the LOS
Compound class: core oligosaccharide, LOS
Reference(s) to other database(s): GTC:G41201OQ, GlycomeDB:
37804
- Compound ID: 10670
|
b-D-ManpNAcA-(1-?)-+
|
L-Thr2Ac-(1-2)-+ |
| |
-3)-a-D-FucpN-(1-3)-a-D-GalpNAc-(1-3)-a-L-Rhap-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
- Compound ID: 3001
|
b-D-GlcpNAc-(1-2)-+
|
-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1-2)-a-L-Rhap-(1-2)-a-L-Rhap-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Reference(s) to other database(s): GTC:G84110KK, GlycomeDB:
34700
- Compound ID: 9474
Structure type: homopolymer
Compound class: CPS
- Compound ID: 9475
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Reference(s) to other database(s): GTC:G01875SI
- Compound ID: 10686
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Reference(s) to other database(s): GTC:G85513YQ
- Compound ID: 10702
|
-3)-a-D-GlcpNAc-(1-2)-b-D-Manp-(1-3)-b-D-Manp2(70%)Ac-(1-4)-b-D-GlcpA-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Reference(s) to other database(s): GTC:G39157QE
- Compound ID: 10668
|
a-D-GlcpA-(1-3)-+
|
a-D-GlcpA-(1-2)-+ |
| |
b-D-Glcp-(1-6)-a-D-Galp-(1-4)-b-D-GlcpA-(1-4)-b-D-GlcpA-(1-3)-+
|
-4)-b-D-Glcp-(1-4)-a-D-GalpA-(1-4)-a-D-Galp-(1-
|
S-2)-+ |
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Structure type: polymer chemical repeating unit
Compound class: EPS
Reference(s) to other database(s): GTC:G07069AE
- Compound ID: 7153
|
3HO2,3MePro-5-oxo-(1-3)-+
|
-2)-b-D-Quip3N-(1-3)-a-L-Rhap2Ac-(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): GlycomeDB:
33702
- Compound ID: 8192
|
S-3HOBut-(1-4)-+
|
-3)-a-L-6dTalpNAc4(75%)Ac-(1-4)-a-L-FucpNAc-(1-4)-a-L-FucpNAc-(1-4)-a-L-FucpNAc-(1-3)-b-D-QuipNAc4N-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
- Compound ID: 10681
|
a-D-GlcpN-(1-4)-a-D-GalpA-(1-7)-L-gro-a-D-manHepp-(1-7)-+ b-D-Galp-(1-4)-+ /Variants 0/-+
| | |
Subst-(1-5)-a-Kdop-(2-6)-a-D-GlcpN-(1-4)-a-D-GalpA-(1-3)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/
|
b-D-Glcp-(1-2)-+
/Variants 0/ is:
a-Kop-(2-4)-
OR (exclusively)
a-Kdop-(2-4)-
Subst = O-antigen |
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Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
- Compound ID: 8565
|
R-3HOBut-(1-3)-+
|
-4)-b-D-GlcpNAc3NA-(1-4)-a-L-FucpNAm3Ac-(1-3)-a-D-QuipNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
- Compound ID: 10703
Structure type: polymer chemical repeating unit
Compound class: teichoic acid
Reference(s) to other database(s): GTC:G50382WC
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