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- |
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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)- |
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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- |
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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- |
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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 |
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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- |
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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
Found