Burkholderia cepacia is an opportunistic pathogen involved in pulmonary infections related to cystic fibrosis. A clinical strain, BTS13, was isolated and the production of exopolysaccharides was tested growing the bacteria on two different media, one of which was rich in mannitol as carbon source. The primary structure of the polysaccharides was determined using mostly mass spectrometry and NMR spectroscopy. On both media an exopolysaccharide having the following repeating unit was produced: →5)-β-Kdop-(2→3)-β-D-Galp2Ac-(1→4)-α-D-Galp-(1→3)-β-D-Galp-(1→. This polysaccharide has already been described as the biosynthetic product of another Burkholderia species, B. pseudomallei, the microbial agent causing melioidosis. In addition to this, when grown on the mannitol-rich medium, B. cepacia strain BTS13 produced another polysaccharide that was established to be levan: →6)-β-D-Fruf-(2→. The content of levan was about 20% (w/w) of the total amount of polymers. The ability of B. cepacia to produce these two exopolysaccharides opens new perspectives in the investigation of the role of polysaccharides in lung infections.
NCBI PubMed ID: 14670727Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: cescutti

bbcm.units.it
Institutions: Dipartimento di Biochimica Biofisica e Chimica delle Macromolecole, Universita` di Trieste, Trieste, Italy, Istituto di Chimica e Tecnologia dei Polimeri, CNR, Catania, Italy, Dipartimento di Scienze Biomediche, Universita` di Trieste, Trieste, Italy
Methods: methylation, NMR-2D, NMR, sugar analysis, MALDI-MS
Recent data on the natural occurrence, chemistry, and biochemistry of C8 and C9 aldulosonic acids (3-deoxy-d-manno-oct-2-ulosonic acid, sialic acids, N-acyl derivatives of 5,7-diamino-3,5,7,9-tetradeoxynon-2-ulosonic acids, and some others) as well as on the structures and biological significance of bacterial glycans containing these higher acidic monosaccharides are summarized.
Publication DOI: 10.1016/j.mencom.2011.07.001Journal NLM ID: 9425965Publisher: Moscow: Academy of Sciences of the USSR; Cambridge,UK : Royal Society of Chemistry
Correspondence: knirel

ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Compound ID: 9658
|
a-Neup5Ac-(2-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1--/core oligosaccharide/ |
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Structure type: oligomer
Aglycon: core oligosaccharide
Trivial name: O-unit
Reference(s) to other database(s): GTC:G69440RD
- Compound ID: 9659
Structure type: oligomer
Aglycon: core-lipid A
Trivial name: outer core oligosaccharide
Compound class: core oligosaccharide
Reference(s) to other database(s): GTC:G65627XI
- Compound ID: 9678
Structure type: fragment of a bigger structure
Aglycon: lipid A
Compound class: core oligosaccharide
Reference(s) to other database(s): GTC:G41560CU
- Compound ID: 9661
|
a-Neup5Ac-(2-3)-+
|
b-Galp-(1-3)-b-GalpNAc-(1-4)-b-Galp-(1--/core-lipid A/ |
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Structure type: oligomer
Aglycon: core-lipid A
Trivial name: outer core oligosaccharide
Compound class: core oligosaccharide
Reference(s) to other database(s): GTC:G40852FO
- Compound ID: 9662
|
a-Neup5Ac-(2-3)-+
|
a-Neup5Ac-(2-3)-b-Galp-(1-3)-b-GalpNAc-(1-4)-b-Galp-(1--/core-lipid A/ |
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Structure type: oligomer
Aglycon: core-lipid A
Trivial name: outer core oligosaccharide
Compound class: core oligosaccharide
Reference(s) to other database(s): GTC:G74363YD
- Compound ID: 9663
|
a-Neup5Ac-(2-8)-a-Neup5Ac-(2-3)-b-Galp-(1-3)-b-GalpNAc-(1-4)-b-Galp-(1--/core-lipid A/ |
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Structure type: oligomer
Aglycon: core-lipid A
Trivial name: outer core oligosaccharide
Compound class: core oligosaccharide
Reference(s) to other database(s): GTC:G72844OV
- Compound ID: 9664
|
a-Neup5Ac-(2-3)-+
|
a-Neup5Ac-(2-8)-a-Neup5Ac-(2-3)-b-Galp-(1-3)-b-GalpNAc-(1-4)-b-Galp-(1--/core-lipid A/ |
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Structure type: oligomer
Aglycon: core-lipid A
Trivial name: outer core oligosaccharide
Compound class: core oligosaccharide
Reference(s) to other database(s): GTC:G87999EY
- Compound ID: 9679
Structure type: fragment of a bigger structure
Aglycon: lipid A
Compound class: core oligosaccharide
Reference(s) to other database(s): GTC:G35106WM
- Compound ID: 4570
|
a-D-Glcp-(1-6)-+ a-D-Glcp-(1-4)-b-D-Galp-(1-6)-b-D-Glcp-(1-3)-+
| |
-3)-b-D-GalpNAc-(1-4)-a-Neup5Ac-(2-6)-a-D-Glcp-(1-6)-b-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Reference(s) to other database(s): GTC:G40762DG, GlycomeDB:
15598
- Compound ID: 9656
Structure type: polymer chemical repeating unit
Compound class: O-antigen
- Compound ID: 9660
|
a-L-Fucp-(1-3)-+
|
a-Neup5Ac-(2-3)-b-Galp-(1-4)-b-GlcpNAc-(1--/core-lipid A/ |
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Structure type: oligomer
Aglycon: core-lipid A
Trivial name: outer core oligosaccharide
Compound class: core oligosaccharide
Reference(s) to other database(s): GTC:G34384CX
- Compound ID: 9682
|
a-Kdop-(2-4)-+
|
SUG-(?-8)-a-Kdop-(2-5)-+ |
| |
-4)-a-Kdop-(2-5)-a-Kdop-(2- |
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Structure type: fragment of a bigger structure
Aglycon: lipid A
Compound class: core oligosaccharide
- Compound ID: 9676
|
a-D-GlcpA-(1-2)-L-gro-a-D-manHepp-(1-3)-+
|
b-Galp-(1-4)-+ |
| |
a-Legp5Ac7Ac-(2-6)-b-D-Glcp-(1-4)-D-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/(2->) lipid A/ |
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Structure type: oligomer
Aglycon: (2->) lipid A
Compound class: core oligosaccharide
Reference(s) to other database(s): GTC:G83765VY
- Compound ID: 423
|
b-Kdop-(2-3)-+
|
-3)-b-D-Glcp-(1-4)-b-D-Glcp-(1-4)-a-L-6dTalp2Ac-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS, EPS
Reference(s) to other database(s): GTC:G93694GD, GlycomeDB:
26572
- Compound ID: 711
|
S-3HOBut-(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, O-antigen
- Compound ID: 9680
Structure type: fragment of a bigger structure
Aglycon: lipid A
Compound class: core oligosaccharide
Reference(s) to other database(s): GTC:G42677TP
- Compound ID: 1182
Structure type: polymer chemical repeating unit
Compound class: CPS, O-polysaccharide
Reference(s) to other database(s): GTC:G72257WT, GlycomeDB:
25178
- Compound ID: 5597
Structure type: polymer chemical repeating unit
Trivial name: K-antigen
Compound class: CPS, EPS
Reference(s) to other database(s): GTC:G30034BK, GlycomeDB:
7846
- Compound ID: 4499
Structure type: polymer chemical repeating unit
Compound class: CPS
Reference(s) to other database(s): GTC:G04480ZC, GlycomeDB:
15656
- Compound ID: 9677
|
b-Galp-(1-4)-b-Glcp-(1-4)-+
|
a-D-GlcpA-(1-2)-+ |
| |
D-Ala-(1-7)-a-Legp5Ac-(2-3)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/(2->) lipid A/
|
b-GlcpA-(1-2)-+ |
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Structure type: oligomer
Aglycon: (2->) lipid A
Compound class: core oligosaccharide
- Compound ID: 9643
Structure type: polymer chemical repeating unit
Compound class: CPS
Reference(s) to other database(s): GTC:G66252LZ
- Compound ID: 4660
|
GroN-(2-6)-+ GroN-(2-6)-+
| |
-4)-a-D-GalpA-(1-4)-a-Neup5Ac-(2-3)-b-D-GalpA-(1-3)-b-D-QuipNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
- Compound ID: 9657
|
GroN-(2-6)-+ GroN-(2-6)-+
| |
-3)-a-D-GalpA-(1-4)-a-Neup5Ac-(2-3)-b-D-GalpA-(1-3)-b-D-GlcpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
- Compound ID: 1370
|
a-Neup5Ac-(2-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-+
|
-4)-b-D-Glcp-(1-4)-b-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Trivial name: PS-Ia
Compound class: CPS, EPS
Reference(s) to other database(s): GTC:G97670WK, GlycomeDB:
15760
- Compound ID: 4077
Structure type: suggested polymer biological repeating unit
Compound class: O-polysaccharide, O-antigen
Reference(s) to other database(s): GlycomeDB:
33683
- Compound ID: 9642
Structure type: polymer chemical repeating unit
Compound class: CPS
Reference(s) to other database(s): GTC:G29190YE
- Compound ID: 4901
|
a-Kdnp-(2-4)-+
|
-3)-b-D-Glcp-(1-2)-a-D-GlcpA3Ac-(1-3)-a-D-Manp-(1-3)-a-D-Glcp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS
Reference(s) to other database(s): GTC:G17686NX
- Compound ID: 7381
|
-8)-a-8eLegp5Ac7Ac-(2-4)-b-D-GlcpA-(1-4)-b-D-GlcpA-(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:G93675TK, GlycomeDB:
34660
- 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: 9645
Structure type: polymer chemical repeating unit
Compound class: O-antigen
Reference(s) to other database(s): GTC:G94419SF
- Compound ID: 9158
|
-4)-a-8eLegp5Ac7Ac-(2-6)-a-D-Galp-(1-3)-a-L-FucpNAc-(1-3)-a-D-GlcpNAc-(1- |
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Structure type: suggested polymer biological repeating unit
Compound class: O-polysaccharide, O-antigen
Reference(s) to other database(s): GTC:G69233GH, GlycomeDB:
37822
- Compound ID: 8580
|
b-D-GlcpNAc-(1-2)-+
|
-6)-b-D-Glcp-(1-6)-b-D-Galp-(1-3)-b-D-GalpNAc-(1-4)-b-Kdop-(2- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Reference(s) to other database(s): GTC:G82104LF, GlycomeDB:
37290
- Compound ID: 9666
Structure type: polymer chemical repeating unit
Compound class: O-antigen
Reference(s) to other database(s): GTC:G75634IE
- Compound ID: 9668
Structure type: polymer chemical repeating unit
Trivial name: teichulosonic acid
Compound class: cell wall polysaccharide, teichulosonic acid
- Compound ID: 9669
|
/Variants 0/-+
|
-4)-4HOBut-(1-7)-b-Psep5Ac-(2-
/Variants 0/ is:
a-D-Galp3Me-(1-4)-
OR (exclusively)
a-D-Galp2Me3Me-(1-4)- |
Show graphically |
Structure type: polymer chemical repeating unit
Trivial name: teichulosonic acid
Compound class: cell wall polysaccharide
- Compound ID: 4675
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Reference(s) to other database(s): GlycomeDB:
33721
- Compound ID: 9059
|
D-Ala-(1-7)-+
|
-8)-a-Legp5Ac-(2-4)-b-D-GlcpA-(1-3)-b-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): GlycomeDB:
37811
- Compound ID: 9644
|
b-Kdop-(2-3)-+
|
-4)-a-L-6dTalpNAc-(1-3)-a-D-GlcpNAc-(1-3)-a-L-FucpNAc-(1-3)-b-D-GlcpNAc-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: CPS
Reference(s) to other database(s): GTC:G99783JG
- Compound ID: 2900
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Reference(s) to other database(s): GTC:G04744LA, GlycomeDB:
26095
- Compound ID: 9646
|
-2)-b-D-Quip3NAc-(1-3)-a-L-Rhap-(1-5)-a-Kdop-(2-3)-b-L-Rhap2Ac-(1-4)-b-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:G11138KZ
- Compound ID: 9647
|
b-D-GlcpNAc-(1-2)-+
|
-4)-b-Kdop-(2-6)-b-D-Glcp-(1-6)-b-D-Galp3Ac4Ac-(1-3)-b-D-GalpNAc-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-antigen
Reference(s) to other database(s): GTC:G28821DP
- Compound ID: 9649
Structure type: polymer chemical repeating unit
; n=20
Trivial name: teichulosonic acid
Compound class: cell wall polysaccharide
Reference(s) to other database(s): GTC:G91121EF
- Compound ID: 9650
Structure type: polymer chemical repeating unit
; n=20
Trivial name: teichulosonic acid
Compound class: cell wall polysaccharide
Reference(s) to other database(s): GTC:G67638CH
- Compound ID: 9651
Structure type: polymer chemical repeating unit
; n=20
Trivial name: teichulosonic acid
Compound class: cell wall polysaccharide
Reference(s) to other database(s): GTC:G61706LV
- Compound ID: 9652
|
b-D-Galp3(%)Me-(1-9)-+
|
b-D-Galp3(%)Me-(1-9)-a-Kdnp-(2-4)-b-Kdnp |
Show graphically |
Structure type: oligomer
Trivial name: teichulosonic acid
Compound class: cell wall polysaccharide
Reference(s) to other database(s): GTC:G90106AF
- Compound ID: 9653
Structure type: polymer chemical repeating unit
; n=20
Trivial name: teichulosonic acid
Compound class: cell wall polysaccharide
Reference(s) to other database(s): GTC:G91010VS
- Compound ID: 811
|
a-Neup5Ac-(2-3)-b-D-Galp-(1-3)-b-D-GlcpNAc-(1-3)-+
|
-4)-b-D-Galp-(1-4)-b-D-Glcp-(1- |
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Structure type: polymer chemical repeating unit
Trivial name: PS-Ib
Compound class: CPS, O-antigen
Reference(s) to other database(s): GTC:G05217ZJ, GlycomeDB:
15761
- Compound ID: 3643
|
b-D-Galp-(1-6)-+ a-Neup5Ac-(2-3)-+
| |
-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-Glcp-(1-3)-b-D-Glcp-(1-2)-b-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS
Reference(s) to other database(s): GTC:G94542ED, GlycomeDB:
15633
- Compound ID: 934
|
a-Neup5Ac-(2-3)-b-D-Galp-(1-4)-+
|
-4)-b-D-Glcp-(1-6)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Trivial name: PS-III
Compound class: CPS, EPS, polysaccharide
Reference(s) to other database(s): GTC:G35073UM, GlycomeDB:
11408, CCSD:
43274, CBank-STR:17387
- Compound ID: 4067
|
a-Neup5Ac-(2-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-6)-+
|
-4)-a-D-Glcp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS
Reference(s) to other database(s): GTC:G45191WA, GlycomeDB:
4639
- Compound ID: 4068
|
b-D-Glcp-(1-3)-+
|
a-Neup5Ac-(2-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-6)-+ |
| |
-4)-a-D-Glcp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS
Reference(s) to other database(s): GTC:G14251NX, GlycomeDB:
27671
- Compound ID: 4069
|
a-Neup5Ac-(2-3)-b-D-Galp-(1-3)-+
|
-6)-b-D-Glcp-(1-3)-b-D-Galp-(1-4)-b-D-Glcp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS
Reference(s) to other database(s): GTC:G82977FE, GlycomeDB:
11178
- Compound ID: 2571
|
a-Neup5Ac-(2-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-6)-+
|
-4)-a-D-Glcp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS
Reference(s) to other database(s): GTC:G16684MV, GlycomeDB:
27673
- Compound ID: 221
|
a-Neup5Ac-(2-3)-+
|
-4)-b-D-Galp-(1-4)-b-L-Rhap-(1-4)-b-D-Glcp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS
Reference(s) to other database(s): GTC:G62462RE, GlycomeDB:
27674
- Compound ID: 9280
|
a-D-Galp-(1-3)-+
|
a-Neup5Ac-(2-6)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-+ |
| |
-4)-b-D-Galp-(1-4)-b-L-Rhap-(1-4)-b-D-Glcp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS, O-polysaccharide, O-antigen
Reference(s) to other database(s): GTC:G87088VU, GlycomeDB:
37829
- Compound ID: 9655
|
a-Neu5Ac-(2-6)-+
|
-6)-b-D-Galf-(1-3)-b-D-GalpNAc-(1-3)-b-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-antigen
Reference(s) to other database(s): GTC:G03960MM
- Compound ID: 9667
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Reference(s) to other database(s): GTC:G03214KE
- Compound ID: 7525
|
b-Psep5Ac7Ac-(2-6)-+
|
-3)-a-D-Galp-(1-6)-a-D-GlcpNAc-(1-4)-a-D-GalpA-(1-3)-b-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:G04039XF, GlycomeDB:
27639
- Compound ID: 9670
Structure type: polymer chemical repeating unit
Trivial name: teichulosonic acid
Compound class: cell wall polysaccharide, teichulosonic acid
- Compound ID: 9671
|
/Variants 0/-+
|
-3)-b-D-Galp-(1-4)-4HOBut-(1-7)-b-Psep5Ac-(2-
/Variants 0/ is:
a-D-Galp3Me-(1-4)-
OR (exclusively)
a-D-Galp2Me3Me-(1-4)- |
Show graphically |
Structure type: polymer chemical repeating unit
Trivial name: teichulosonic acid
Compound class: cell wall polysaccharide
- Compound ID: 9672
|
/Variants 0/-+
|
-3)-b-D-Galp-(1-4)-4HOBut-(1-7)-b-Psep5Ac-(2-
/Variants 0/ is:
b-L-Rhap-(1-4)-
OR (exclusively)
a-D-Galp3Me-(1-4)-
OR (exclusively)
a-D-Galp2Me3Me-(1-4)- |
Show graphically |
Structure type: polymer chemical repeating unit
Trivial name: teichulosonic acid
Compound class: cell wall polysaccharide
- Compound ID: 9673
Structure type: polymer chemical repeating unit
Trivial name: teichulosonic acid
Compound class: cell wall polysaccharide, teichulosonic acid
- Compound ID: 9674
|
a-D-Galp-(1-4)-+
|
-3)-b-D-Glcp-(1-4)-3,4HOBut-(1-7)-b-Psep5Ac-(2- |
Show graphically |
Structure type: polymer chemical repeating unit
Trivial name: teichulosonic acid
Compound class: cell wall polysaccharide
- Compound ID: 9675
Structure type: polymer chemical repeating unit
Trivial name: teichulosonic acid
Compound class: cell wall polysaccharide
- Compound ID: 9681
Structure type: fragment of a bigger structure
Aglycon: lipid A
Compound class: core oligosaccharide
Reference(s) to other database(s): GTC:G52410ZE