With the continuing advancement of carbohydrate chemical synthesis, bacterial glycomes have become increasingly attractive and accessible synthetic targets. Although bacteria also produce carbohydrate-containing secondary metabolites, our review here will cover recent chemical synthetic efforts on bacterial surface glycans. The obtained compounds are excellent candidates for the development of improved structurally defined glycoconjugate vaccines to combat bacterial infections. They are also important probes for investigating glycan–protein interactions. Glycosylation strategies applied for the formation of some challenging glycosidic bonds of various uncommon sugars in a number of recently synthesized bacterial surface glycans are highlighted.
- Compound ID: 14821
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a-Neup5Ac-(2-3)-+ a-D-Glcp-(1-4)-+
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b-D-Galp-(1-3)-b-D-GalpNAc-(1-4)-b-D-Galp-(1-3)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/(->1)6-N-(2-tetradecylhexadecanoyl)aminohexanol SMILES CCCCCCCCCCCCCCC(CCCCCCCCCCCCCC)C(NCCCCCC{1}O)=O/ |
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Structure type: oligomer
Aglycon: (->1)6-N-(2-tetradecylhexadecanoyl)aminohexanol SMILES CCCCCCCCCCCCCCC(CCCCCCCCCCCCCC)C(NCCCCCC{1}O)=O
Compound class: core oligosaccharide
Reference(s) to other database(s): GTC:G99874JB
- Compound ID: 14801
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L-gro-a-D-manHepp-(1-4)-+
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a-D-GlcpNAc-(1-4)-b-D-ManpNAc3NAcA-(1-3)-b-L-FucpNAc4NMe-(1-6)-b-D-GlcpNAc-(1--/(->1)(CH2)3NH2 (3-aminopropyl)/ |
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Structure type: oligomer
Aglycon: (->1)(CH2)3NH2 (3-aminopropyl)
Compound class: LPS
Reference(s) to other database(s): GTC:G20309XZ
- Compound ID: 12758
Structure type: oligomer
Trivial name: pilin glycan trisaccharide (7-N-Formylamino-5-N-[(R)-3-hydroxybutyryl]-α-pseudaminosyl-(2→4)-β-D-xylopyranosyl-(1→3)-2-acetamido-2-deoxy-α/β-D-fucopyranose), pilin trisaccharide
- Compound ID: 14777
Structure type: polymer chemical repeating unit
; n=3,4
Aglycon: (->1)(CH2)3NH2
Compound class: CPS
Reference(s) to other database(s): GTC:G48944PP
- Compound ID: 14778
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b-D-Glcp-(1-3)-{{{-b-D-GlcpA-(1-4)-b-D-Glcp-(1-3)-}}}/n=1-2/-b-D-GlcpA-(1-4)-b-D-Glcp-(1--/(->1)(CH2)3NH2/ |
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Structure type: oligomer
Aglycon: (->1)(CH2)3NH2
Compound class: CPS
Reference(s) to other database(s): GTC:G97495OL
- Compound ID: 14795
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b-D-Galf-(1-3)-+
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Pyr-(2-6:2-4)-b-D-Galp-(1-3)-a-D-FucpNAc4N-(1-4)-b-D-GalpNAc-(1--/(->1)p-methoxyphenol/ |
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Structure type: oligomer
Aglycon: (->1)p-methoxyphenol
Compound class: CPS
- Compound ID: 14775
Structure type: polymer chemical repeating unit
; n=1-4
Aglycon: (->1)CH2-CH2-CH=CH2
Compound class: CPS
Reference(s) to other database(s): GTC:G61451FW
- Compound ID: 14807
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{{{-b-D-Galf-(1-3)-a-D-Galp-(1-3)-}}}/n=4/-a-D-GlcpNAc-(1---P---P----/(->1)farnesol/ |
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Structure type: oligomer
Aglycon: (->1)farnesol
Compound class: O-polysaccharide
- Compound ID: 14829
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b-D-Manp-(1-4)-a-D-GlcpA-(1-3)-a-D-Manp-(1-2)-a-D-Manp-(1-3)-b-D-Glcp-(1-1)-EtN |
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Structure type: oligomer
Trivial name: biofilm
Compound class: EPS
- Compound ID: 14800
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Ac-4)-{{{-a-D-GalpNAcA3Ac-(1-4)-}}}/n=4-7/-a-D-GalpNAcA3Ac-(1-1)-Me |
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Structure type: oligomer
Compound class: CPS
- Compound ID: 14779
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Gro-(1--P--4)--a-D-Glcp-(1-4)-a-D-Galp-(1-3)-b-D-Galp-(1-4)-b-D-Glcp-(1-1)-EtN |
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Structure type: oligomer
Compound class: CPS
- Compound ID: 14824
Structure type: polymer chemical repeating unit
; n=1-3
Aglycon: (->1)(CH2)2N3 (2-azidoethyl)
Trivial name: GAS-PS
Compound class: cell wall polysaccharide
Reference(s) to other database(s): GTC:G59445KA
- Compound ID: 14774
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{{{-b-D-Ribf-(1-1)-D-Rib-ol-(5--P--3)--}}}/n=3-9/-b-D-Ribf-(1-1)-D-Rib-ol-(5---P---/(->1)(CH2)5NH2/ |
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Structure type: oligomer
; n=3,5,7,9
Aglycon: (->1)(CH2)5NH2
Compound class: CPS
Reference(s) to other database(s): GTC:G36326JQ
- Compound ID: 14790
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b-D-ManpNAcA-(1-4)-a-L-FucpNAc3Ac-(1-3)-b-D-FucpNAc-(1--/(1->1)(CH2)3NH2, or (CH2)4NH2, or (CH2)5NH2/ |
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Structure type: oligomer
Aglycon: (1->1)(CH2)3NH2, or (CH2)4NH2, or (CH2)5NH2
Compound class: CPS
Reference(s) to other database(s): GTC:G73653TH
- Compound ID: 14781
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b-D-GlcpA-(1-4)-b-D-Glcp-(1-4)-a-D-Glcp-(1-4)-a-D-Galp-(1--/(->1)(CH2)5NH2/ |
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Structure type: oligomer
Aglycon: (->1)(CH2)5NH2
Compound class: CPS
Reference(s) to other database(s): GTC:G05921XW
- Compound ID: 14782
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b-D-Glcp-(1-4)-a-D-Glcp-(1-4)-a-D-Galp-(1-4)-b-D-GlcpA-(1--/(->1)(CH2)5NH2/ |
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Structure type: oligomer
Aglycon: (->1)(CH2)5NH2
Compound class: CPS
Reference(s) to other database(s): GTC:G49679DC
- Compound ID: 14783
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a-D-Galp-(1-4)-b-D-GlcpA-(1-4)-b-D-Glcp-(1-4)-a-D-Glcp-(1--/(->1)(CH2)5NH2/ |
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Structure type: oligomer
Aglycon: (->1)(CH2)5NH2
Compound class: CPS
Reference(s) to other database(s): GTC:G80078KL
- Compound ID: 14784
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a-D-Glcp-(1-4)-a-D-Galp-(1-4)-b-D-GlcpA-(1-4)-b-D-Glcp-(1--/(->1)(CH2)5NH2/ |
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Structure type: oligomer
Aglycon: (->1)(CH2)5NH2
Compound class: CPS
Reference(s) to other database(s): GTC:G10586WE
- Compound ID: 14802
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b-D-Glcp-(1-3)-a-L-FucpNAc-(1-3)-b-D-FucpNAc-(1--/(->1)(CH2)3NH2 (3-aminopropyl)/ |
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Structure type: oligomer
Aglycon: (->1)(CH2)3NH2 (3-aminopropyl)
Compound class: O-polysaccharide
Reference(s) to other database(s): GTC:G66933BT
- Compound ID: 14810
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a-Parp-(1-3)-a-D-Manp-(1-4)-a-L-Rhap-(1-3)-a-D-Galp-(1--/(->1)(CH2)3NH2 (3-aminopropyl)/ |
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Structure type: oligomer
Aglycon: (->1)(CH2)3NH2 (3-aminopropyl)
Compound class: O-polysaccharide
Reference(s) to other database(s): GTC:G89695AF
- Compound ID: 14776
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b-L-Rhap-(1-4)-b-D-Glcp-(1-3)-+
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a-D-GlcpA-(1-6)-a-D-Glcp-(1-2)-a-L-Rhap-(1-3)-a-L-Rhap-(1--/(->1)(CH2)5NH2/ |
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Structure type: oligomer
Aglycon: (->1)(CH2)5NH2
Compound class: CPS
Reference(s) to other database(s): GTC:G28337FJ
- Compound ID: 14780
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a-D-Glcp-(1-2)-a-D-Glcp-(1-3)-+
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a-D-Galp-(1-3)-a-L-FucpNAc-(1-3)-b-D-GalpNAc-(1-4)-b-D-ManpNAcA-(1--/(->1)(CH2)5NH2/ |
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Structure type: oligomer
Aglycon: (->1)(CH2)5NH2
Compound class: CPS
Reference(s) to other database(s): GTC:G64307BB
- Compound ID: 14806
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{{{-a-D-Glcp-(1-2)-a-D-Glcp-(1-3)-}}}/n=0-2/-a-D-Glcp-(1-2)-a-D-Glcp-(1--/(->1)(CH2)5NH2 (5-aminopentyl)/ |
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Structure type: oligomer
Aglycon: (->1)(CH2)5NH2 (5-aminopentyl)
Compound class: O-polysaccharide
- Compound ID: 14785
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a-Neup5Ac-(2-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-+
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b-D-Glcp-(1-4)-+ |
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a-Neup5Ac-(2-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-b-D-Galp-(1-1)-EtN |
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Structure type: oligomer
Compound class: CPS
- Compound ID: 14786
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b-D-Galp-(1-6)-+
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a-Neup5Ac-(2-3)-b-D-Galp-(1-4)-b-D-Glcp2Ac-(1-3)-b-D-Galp-(1-4)-b-D-Glcp-(1-3)-b-D-Glcp-(1-1)-EtN |
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Structure type: oligomer
Compound class: CPS
- Compound ID: 14787
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a-Neup5Ac-(2-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-6)-a-D-Glcp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-1)-EtN |
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Structure type: oligomer
Compound class: CPS
- Compound ID: 14808
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b-L-Rhap-(1-4)-a-L-Rhap-(1-2)-a-L-Rhap-(1-2)-a-D-GalpA-(1-3)-a-D-GalpNAc-(1--/(->1)p-methoxyphenyl/ |
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Structure type: oligomer
Aglycon: (->1)p-methoxyphenyl
Compound class: O-polysaccharide
Reference(s) to other database(s): GTC:G56321UL
- Compound ID: 14794
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?%Subst-(1-2)-+
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b-D-GlcpNAc-(1-3)-a-D-Galp-(1-2)-a-D-6daltHepp3(%)Me-(1--/(->1)(CH2)8NH2/
Subst = O-methyl phosphamide (OHPO(NH2)OMe) = SMILES {1}OP(OC)(N)=O |
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Structure type: oligomer
Aglycon: (->1)(CH2)8NH2
Compound class: CPS
- Compound ID: 14825
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S-Pyr-(2-6:2-4)-b-D-ManpNAc3(%)Ac-(1-4)-b-D-GlcpNAc3(%)Ac-(1-6)-b-D-GlcpN(%)Ac-(1--/(->1)(CH2)5NH(CO)(CH2)2SH/ |
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Structure type: oligomer
Aglycon: (->1)(CH2)5NH(CO)(CH2)2SH
Compound class: cell wall polysaccharide
- Compound ID: 14815
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b-D-Manp-(1-4)-+
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a-L-Rhap-(1-3)-b-D-GlcpNAc-(1-3)-a-D-Galp-(1-1)-Oc |
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Structure type: oligomer
Compound class: O-polysaccharide
- Compound ID: 14828
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D-GroA-(2-1)-+
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{{{-a-D-GlcpNAc-(1-3)-a-D-GlcpNAc-(6--P--6)--}}}/n=1-2/-b-D-Glcp-(1-6)-b-D-Glcp-(1-6)-b-D-Glcp-(1--/(->1)(CH2)3NH2 (3-aminopropyl)/ |
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Structure type: oligomer
Aglycon: (->1)(CH2)3NH2 (3-aminopropyl)
Compound class: lipoteichoic acid
- Compound ID: 14793
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a-D-6dmanHepp-(1--P--3)--b-D-6dmanHepp-(1-3)-a-D-6dmanHepp-(1--/(1->1)(CH2)5NH2/ |
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Structure type: oligomer
Aglycon: (1->1)(CH2)5NH2
Compound class: CPS
Reference(s) to other database(s): GTC:G02238KL
- Compound ID: 14820
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a-Kdop-(2-4)-+
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a-D-Manp-(1-5)-a-Kdop-(2-6)-b-D-GlcpNAc-(1-6)-a-D-GlcpNAc-(1--/(->1)(CH2)3NH2 (3-aminopropyl)/ |
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Structure type: oligomer
Aglycon: (->1)(CH2)3NH2 (3-aminopropyl)
Compound class: core oligosaccharide
Reference(s) to other database(s): GTC:G84063DG
- Compound ID: 14827
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a-D-Manp-(1-2)-a-D-Manp-(1-2)-a-D-Rhap3Me-(1-3)-a-D-Rhap-(1--/(->1)(CH2)3NH2 (3-aminopropyl)/ |
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Structure type: oligomer
Aglycon: (->1)(CH2)3NH2 (3-aminopropyl)
Compound class: EPS
Reference(s) to other database(s): GTC:G57126BF
- Compound ID: 14826
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a-D-Fucf-(1-2)-a-D-Fucf-(1-4)-D-gro-b-D-galHepp-(1-3)-D-gro-b-D-galHepp-(1-6)-D-gro-b-D-galHepp-(1-3)-D-gro-b-D-galHepp-(1--/(->1)(CH2)3NH2 (3-aminopropyl)/ |
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Structure type: oligomer
Aglycon: (->1)(CH2)3NH2 (3-aminopropyl)
Compound class: cell wall polysaccharide
Reference(s) to other database(s): GTC:G83502GY
- Compound ID: 14803
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/Variants 0/-+
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R-3HOBut-(1-3)-b-D-GlcpNAc3NA-(1-4)-a-L-FucpN3Ac-(1-3)-a-D-QuipNAc-(1--/(->1)(CH2)3NH2 (3-aminopropyl)/
/Variants 0/ is:
Am-2)-
OR (exclusively)
Ac-2)- |
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Structure type: oligomer
Aglycon: (->1)(CH2)3NH2 (3-aminopropyl)
Compound class: O-polysaccharide
- Compound ID: 14813
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a-D-Fucp3NAc-(1-3)-b-D-Manp-(1-3)-b-D-Glcp-(1-3)-b-D-GlcpNAc-(1--/(->1)p-methoxyphenyl/ |
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Structure type: oligomer
Aglycon: (->1)p-methoxyphenyl
Compound class: O-polysaccharide
Reference(s) to other database(s): GTC:G54966ER
- Compound ID: 14811
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b-D-Manp-(1-4)-a-D-Glcp-(1-3)-a-L-QuipNAc-(1-3)-a-D-GlcpNAc-(1--/(->1)p-methoxyphenyl/ |
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Structure type: oligomer
Aglycon: (->1)p-methoxyphenyl
Compound class: O-polysaccharide
Reference(s) to other database(s): GTC:G42174LP
- Compound ID: 14804
Structure type: polymer chemical repeating unit
; n=1,2
Aglycon: (->1)(CH2)3N3 (3-Azidopropyl)
Compound class: O-polysaccharide
Reference(s) to other database(s): GTC:G06700QW
- Compound ID: 14812
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b-D-GlcpNAc-(1-3)-b-D-Galp-(1-3)-a-D-GalpNAc-(1-3)-b-D-GlcpNAc-(1-6)-a-D-Glcp-(1-1)-EtN |
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Structure type: oligomer
Compound class: O-polysaccharide
- Compound ID: 14792
Structure type: polymer chemical repeating unit
; n=1-4
Aglycon: (->1)(CH2)3NH2
Compound class: CPS, O-polysaccharide
Reference(s) to other database(s): GTC:G09650IH
- Compound ID: 14822
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{{{-a-Bradyrhizosep-(1-7)-}}}/n=2-5/-a-Bradyrhizosep-(1-1)-Pr
Bradyrhizose = 4,9-cyclo-6-deoxy-8-C-methyl-D-xylo-D-galacto-nonose = SMILES O{1}[C@@H]1[C@@H]([C@H]([C@]2([C@@H](C{7}[C@H]([C@]([C@H]2O)(C)O)O)O1)O)O)O |
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Structure type: oligomer
Compound class: O-antigen
- Compound ID: 14805
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a-D-4dxylHexp-(1-2)-b-L-Rhap-(1-4)-b-D-GlcpNAc-(1--/(->1)(CH2)3NH2 (3-aminopropyl)/ |
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Structure type: oligomer
Aglycon: (->1)(CH2)3NH2 (3-aminopropyl)
Compound class: O-polysaccharide
Reference(s) to other database(s): GTC:G77209DZ
- Compound ID: 14796
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a-D-GalpN-(1-3)-+
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Cho-(1--P--2)--b-D-Galp-(1-3)-b-D-GalpNAc-(1-3)-Gro-(1-P |
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Structure type: oligomer
Trivial name: zwitterionic polysaccharide (ZPS)
- Compound ID: 14816
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b-L-Rhap-(1-4)-b-D-GlcpNAc-(1-4)-a-D-GalpA-(1-3)-a-D-Manp-(1-3)-b-D-GlcpNAc-(1-1)-EtN |
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Structure type: oligomer
Compound class: O-polysaccharide
- Compound ID: 14819
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D-GroA1NH2-(2--P--3)--b-D-GalpNAc-(1-4)-b-D-Galp-(1-3)-b-D-FucpNAc4N-(1-1)-iPr |
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Structure type: oligomer
Compound class: O-polysaccharide
- Compound ID: 14823
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b-D-QuipNAc4NAc-(1-3)-+
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b-L-ArapNAc3NAc4NAc-(1-4)-b-D-GlcpNAc3NAcA6NH2-(1-3)-a-L-Rhap-(1-2)-a-L-Rhap-(1-4)-a-D-Galp-(1-1)-Me
AraN3N4N = 2,3,4-triamino-2,3,4-trideoxy-L-arabinose |
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Structure type: oligomer
Compound class: O-polysaccharide
- Compound ID: 14799
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b-D-GlcpA-(1-3)-b-D-GlcpNAc-(1-2)-a-D-GalpA-(1-3)-b-D-GalpNAc-(1-1)-Pr |
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Structure type: oligomer
Compound class: CPS
- Compound ID: 14814
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a-L-Fucp-(1-3)-b-D-Manp-(1-3)-a-D-Manp-(1-3)-a-L-Fucp-(1-3)-b-D-GalpNAc-(1--/(->1)p-methoxyphenyl/ |
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Structure type: oligomer
Aglycon: (->1)p-methoxyphenyl
Compound class: O-polysaccharide
Reference(s) to other database(s): GTC:G44040OX
- Compound ID: 14817
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R-Pyr-(2-6:2-4)-a-D-Galp-(1-3)-a-L-Fucp-(1-6)-a-D-Galp-(1-3)-a-L-Fucp-(1-3)-b-D-GlcpNAc-(1--/(->1)(CH2)3NH2 (3-aminopropyl)/ |
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Structure type: oligomer
Aglycon: (->1)(CH2)3NH2 (3-aminopropyl)
Compound class: O-polysaccharide
- Compound ID: 14797
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a-D-Manp-(1-4)-{{{-b-D-Rhap-(1-3)-a-D-Manp-(1-4)-}}}/n=0-8/-b-D-Rhap-(1--/(->1)(CH2)5NH2 (5-aminopentyl)/ |
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Structure type: oligomer
Aglycon: (->1)(CH2)5NH2 (5-aminopentyl)
Compound class: CPS
- Compound ID: 14788
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a-L-Rhap-(1-4)-+
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b-D-Galp-(1-3)-a-D-GalpA-(1-2)-a-L-Rhap-(1-2)-a-L-Rhap-(1-2)-a-L-Rhap-(1--/(->1)(CH2)5NH2/ |
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Structure type: oligomer
Aglycon: (->1)(CH2)5NH2
Compound class: CPS
Reference(s) to other database(s): GTC:G19988YH
- Compound ID: 14789
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b-D-Glcp-(1-3)-a-D-GlcpNAc-(1-4)-a-D-GalpNAc-(1-3)-a-D-GlcpNAc-(1-6)-a-D-GlcpNAc-(1--/(->1)(CH2)3NH2/ |
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Structure type: oligomer
Aglycon: (->1)(CH2)3NH2
Compound class: CPS
Reference(s) to other database(s): GTC:G53765LG
- Compound ID: 14791
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a-D-FucNAc-(1-4)-a-D-GalpNAcA-(1-4)-a-D-GalpNAcA-(1--/(->1)(CH2)5NH2/ |
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Structure type: oligomer
Aglycon: (->1)(CH2)5NH2
Compound class: CPS
Reference(s) to other database(s): GTC:G09439SZ
- Compound ID: 14798
Structure type: oligomer
Aglycon: (->1)(CH2)5NH2 (5-aminopentyl)
Compound class: CPS
Reference(s) to other database(s): GTC:G60729LN
- Compound ID: 14809
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a-Tyvp-(1-3)-a-D-Manp-(1-4)-a-L-Rhap-(1-3)-a-D-Galp-(1--/(->1)(CH2)3NH2 (3-aminopropyl)/ |
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Structure type: oligomer
Aglycon: (->1)(CH2)3NH2 (3-aminopropyl)
Compound class: O-polysaccharide
Reference(s) to other database(s): GTC:G46528GO
- Compound ID: 14818
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a-L-Rhap2Ac-(1-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1-3)-b-D-GlcpNAc6Ac-(1--/(->1)p-methoxyphenyl/ |
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Structure type: oligomer
Aglycon: (->1)p-methoxyphenyl
Compound class: O-polysaccharide
Reference(s) to other database(s): GTC:G87129CO