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1. (Article ID: 2839)
Fischer W
'Lipoteichoic acid' of Bifidobacterium bifidum subspeciespennsylvanicum DSM 20239. A lipoglycan with monoglycerophosphate side chain
European Journal of Biochemistry 165 (1987)
639-646
The lipid macroamphiphile of Bifidobacterium bifidum subsp. pennsylvanicum DSM 20239 was extracted with phenol/water and purified by treatment with nucleases and hydrophobic interaction chromatography. From analytical data, the results of Smith degradation, hydrolysis with HF and methylation studies, the following structure is proposed: (formula; see text) where n and m are approximately 7-10 and 8-15, respectively. The monoglycerophosphate residues have the sn-glycero-1-phosphate configuration; 20-50% of them are substituted with L-alanine in ester linkage. The lipid anchor is most likely a galactosyldiacylglycerol, part of which carries a third fatty acid. This is the first example among gram-positive bacteria of a glycerophosphate-containing lipid macroamphiphile that carries the glycerophosphate residues as monomeric side chains on a lipoglycan. Further, it contains L-alanine in place of the D-alanine found in lipoteichoic acids.
NCBI PubMed ID: 3595606Publication DOI: 10.1111/j.1432-1033.1987.tb11488.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Institut für Physiologische Chemie, Universität Erlangen Nürnberg, Erlangen
The publication contains the following compound(s):
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2. (Article ID: 5832)
Pyclik M, Srutkova D, Schwarzer M, Gorska S
Bifidobacteria cell wall-derived exo-polysaccharides, lipoteichoic acids, peptidoglycans, polar lipids and proteins - their chemical structure and biological attributes
International Journal of Biological Macromolecules 147 (2020)
333-349
A variety of health benefits has been documented to be associated with the consumption of probiotic bacteria, namely bifidobacteria and lactobacilli. Thanks to the scientific advances in recent years we are beginning to understand the molecular mechanisms by which bacteria in general and probiotic bacteria in particular act as host physiology and immune system modulators. More recently, the focus has shifted from live bacteria towards bacteria-derived defined molecules, so called postbiotics. These molecules may represent safer alternative compared to the live bacteria while retaining the desired effects on the host. The excellent source of effector macromolecules is the bacterial envelope. It contains compounds that are pivotal in the adhesion phenomenon, provide direct bacteria-to-host signaling capacity and the associated physiological impact and immunomodulatory properties of bacteria. Here we comprehensively review the structure and biological role of Bifidobacterium surface and cell wall molecules: exopolysaccharides, cell wall polysaccharides, lipoteichoic acids, polar lipids, peptidoglycans and proteins. We discuss their involvement in direct signaling to the host cells and their described immunomodulatory effects.
exopolysaccharide, Bacterial antigens, Bifidobacterium, peptidoglycan, lipoteichoic acid, probiotics
NCBI PubMed ID: 31899242Publication DOI: 10.1016/j.ijbiomac.2019.12.227Journal NLM ID: 7909578Publisher: Butterworth-Heinemann
Correspondence: schwarzer

biomed.cas.cz; sabina.gorska

hirszfeld.pl
Institutions: Laboratory of Microbiome Immunobiology, Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Wroclaw, Poland, Laboratory of Gnotobiology, Institute of Microbiology of the Czech Academy of Sciences, Novy Hradek, Czech Republic
The publication contains the following compound(s):
- Compound ID: 14901
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L-Ala-(1-3)-Gro-(1--P--6)--+
|
L-Ala-(1-3)-Gro-(1--P--6)--+ | LIP-(1-1)-+
| | |
{{{-b-D-Galf-(1-5)-}}}/n=10-17/-b-D-Galf-(1-6)-{{{-b-D-Glcp-(1-6)-}}}/n=8-12/-b-D-Galp-(1-3)-Gro
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LIP-(1-2)-+ |
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Structure type: oligomer
Compound class: lipoteichoic acid
- Compound ID: 14895
|
LIP-(1-1)-+
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LIP-(1-?)-+ |
| |
{{{-b-D-Galf-(1-5)-}}}/n=31-34/-/Variants 0/-{{{-Gro-(1--P--2)--}}}/n=13/-Gro-(1--P--6)--b-D-Galf-(1-3)-Gro
|
LIP-(1-2)-+
/Variants 0/ is:
b-D-Galf-(1-3)-
OR (exclusively)
b-D-Galf-(1-2)- |
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Structure type: oligomer
Compound class: lipoteichoic acid
- Compound ID: 14896
|
LIP-(1-1)-+
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LIP-(1-?)-+ |
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{{{-b-D-Glcp-(1-6)-}}}/n=31-34/-/Variants 0/-{{{-Gro-(1--P--2)--}}}/n=13/-Gro-(1--P--6)--b-D-Galf-(1-3)-Gro
|
LIP-(1-2)-+
/Variants 0/ is:
b-D-Glcp-(1-3)-
OR (exclusively)
b-D-Glcp-(1-2)- |
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Structure type: oligomer
Compound class: lipoteichoic acid
- Compound ID: 14898
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a-D-Glcp-(1-2)-+ a-D-Glcp-(1-2)-+ a-D-Glcp-(1-2)-+ a-D-Glcp-(1-2)-+
| | | |
{{{-a-L-Rhap-(1-3)-a-L-Rhap-(1-2)-a-L-Rhap-(1-3)-a-L-Rhap-(1-2)-}}}a-L-Rhap-(1-3)-a-L-Rhap-(1-2)-a-L-Rhap-(1-3)-a-L-Rhap-(1--P--6)--{{{-Man-ol-(4--P--6)--}}}/n=2-5/-Man-ol-(4-P |
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Structure type: oligomer
Compound class: teichoic acid
Reference(s) to other database(s): GTC:G49510FO
- Compound ID: 14899
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a-D-Glcp-(1-3)-+ a-D-Glcp-(1-3)-+
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{{{-a-L-Rhap-(1-2)-a-L-Rhap-(1-2)-}}}a-L-Rhap-(1-2)-a-L-Rhap-(1--P--6)--{{{-Man-ol-(4--P--6)--}}}/n=2-5/-Man-ol-(4-P |
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Structure type: oligomer
Compound class: teichoic acid
Reference(s) to other database(s): GTC:G66126XZ
- Compound ID: 8783
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a-D-Glcp-(1-6)-+
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-6)-a-D-Glcp-(1-3)-b-D-Galf-(1-3)-a-D-Glcp-(1-2)-b-D-Galf-(1-3)-a-D-Galp-(1-3)-a-D-Glcp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: EPS, cell wall polysaccharide
Reference(s) to other database(s): GTC:G66404HH, GlycomeDB:
37313
- Compound ID: 9714
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a-D-Galf-(1-2)-a-L-Rhap-(1-2)-+
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-4)-b-D-Glcp-(1-3)-a-L-Rhap-(1-2)-a-L-Rhap-(1-4)-b-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: EPS
Reference(s) to other database(s): GTC:G17785CI
- Compound ID: 1565
Structure type: polymer chemical repeating unit
Trivial name: CWP, lipoteichoic acid
Compound class: EPS, cell wall polysaccharide, teichoic acid
Reference(s) to other database(s): GTC:G00933AQ
- Compound ID: 11459
Structure type: polymer chemical repeating unit
Compound class: teichoic acid
Reference(s) to other database(s): GTC:G15420JT
- Compound ID: 11463
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-3)-b-D-Galf-(1-3)-a-D-Glcp-(1-2)-b-D-Galf-(1-6)-/Variants 0/-b-D-Galp-(1-
/Variants 0/ is:
a-D-GlcpNAc-(1--P--4)--
OR (exclusively)
a-D-Glcp-(1--P--4)-- |
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Structure type: polymer chemical repeating unit
Compound class: cell wall polysaccharide
- Compound ID: 11603
|
a-D-Galp-(1-3)-+ a-D-Galp-(1-3)-+
| |
-4)-a-D-Glcp-(1-4)-a-D-Man-(1-4)-a-L-Rhap-(1-4)-a-D-Man-(1-4)-a-D-Gal-(1- |
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Structure type: polymer chemical repeating unit
Compound class: EPS
Reference(s) to other database(s): GTC:G41062KO
- Compound ID: 11607
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b-D-Glcp-(1-6)-+ b-D-Galp-(1-4)-+
| |
-4)-a-D-Galp-(1-4)-a-D-Galp-(1-4)-b-D-Glcp-(1-3)-a-D-Galp-(1-3)-b-L-Rhap-(1- |
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Structure type: polymer chemical repeating unit
Compound class: EPS
Reference(s) to other database(s): GTC:G01372QF
- Compound ID: 12506
|
a-D-Glcp-(1-2)-+
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-4)-b-D-Glcp-(1-4)-a-L-6dTalp-(1-4)-a-D-GalpA-(1-4)-a-D-Gal-(1-4)-a-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: EPS
Reference(s) to other database(s): GTC:G67873KO
- Compound ID: 14911
Structure type: polymer chemical repeating unit
Compound class: EPS
Reference(s) to other database(s): GTC:G86179TO
- Compound ID: 14912
Structure type: polymer chemical repeating unit
Compound class: EPS
Reference(s) to other database(s): GTC:G87531DV
- Compound ID: 14903
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a-D-Galf-(1-2)-a-L-Rhap-(1-2)-+
|
-3)-b-D-Glcp-(1-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1-4)-b-D-Galp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: EPS
Reference(s) to other database(s): GTC:G37224VR
- Compound ID: 14897
|
35%L-Ala-(1-3)-Gro-(1--P--6)--+
|
35%L-Ala-(1-3)-Gro-(1--P--6)--+ | LIP-(1-1)-+
| | |
{{{-b-D-Galf-(1-5)-}}}/n=6-9/-b-D-Galf-(1-6)-{{{-b-D-Glcp-(1-6)-}}}/n=8-15/-b-D-Galp-(1-3)-Gro
|
LIP-(1-2)-+ |
Show graphically |
Structure type: oligomer
Compound class: lipoteichoic acid
- Compound ID: 201
Structure type: polymer chemical repeating unit
Trivial name: glucan
Compound class: EPS, cell wall polysaccharide
Reference(s) to other database(s): GTC:G95758CQ, GlycomeDB:
25525
- Compound ID: 14900
Structure type: polymer chemical repeating unit
; n=25
Compound class: teichoic acid
Reference(s) to other database(s): GTC:G32248OD
- Compound ID: 14905
|
a-D-Glcp-(1-2)-+
|
-6)-b-D-Glcp-(1-6)-b-D-Glcp-(1-6)-b-D-Glcp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
; n=6-12
Compound class: cell wall polysaccharide
Reference(s) to other database(s): GTC:G56296IU
- Compound ID: 14906
Structure type: polymer chemical repeating unit
; n=6-12
Compound class: cell wall polysaccharide
Reference(s) to other database(s): GTC:G34207ES
- Compound ID: 14907
Structure type: homopolymer
; n=22
Compound class: cell wall polysaccharide
Reference(s) to other database(s): GTC:G69386QK
- Compound ID: 14908
Structure type: homopolymer
; n=22
Compound class: cell wall polysaccharide
Reference(s) to other database(s): GTC:G77076MY
- Compound ID: 11605
|
b-Glcp-(1-3)-+
|
b-Glcp-(1-3)-+ b-Glcp-(1-3)-+ |
| | |
-2)-a-6dTalp-(1-3)-b-6dTalp-(1-3)-b-6dTalp-(1-3)-b-6dTalp-(1-2)-a-6dTalp-(1-2)-a-6dTalp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: EPS
Reference(s) to other database(s): GTC:G33168ET
- Compound ID: 14909
|
a-D-Glcp-(1-6)-+
|
-3)-a-D-Glcp-(1-3)-a-D-Galp-(1-4)-a-D-Galp-(1-4)-a-D-Galp-(1-2)-a-D-Glcp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: EPS
Reference(s) to other database(s): GTC:G41823JH
- Compound ID: 2912
Structure type: polymer chemical repeating unit
Trivial name: galactan
Compound class: EPS, O-polysaccharide, O-antigen, cell wall polysaccharide
Reference(s) to other database(s): GTC:G51971WH, GlycomeDB:
3478
- Compound ID: 361
|
30%b-D-Glcp-(1-6)-+
|
90%b-D-Glcp-(1-6)-+ |
| |
-3)-b-D-Galf-(1-3)-a-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: EPS, cell wall polysaccharide
Reference(s) to other database(s): GTC:G91263LC, GlycomeDB:
34541
- Compound ID: 2911
|
a-D-Galp-(1-6)-+
|
-2)-a-L-Rhap-(1-3)-a-D-Galp-(1-2)-a-L-Rhap-(1-3)-a-D-Galp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: EPS, cell wall polysaccharide
Reference(s) to other database(s): GTC:G52109UQ, GlycomeDB:
26102
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