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1. (Article ID: 4629)
Valueva OA, Shashkov AS, Zdorovenko EL, Chizhov AO, Kiseleva E, Novik G, Knirel YA
Structures of cell-wall phosphate-containing glycopolymers of Bifidobacterium longum BIM B-476-D
Carbohydrate Research 373 (2013)
22-27
Glycopolymers with oligosaccharyl phosphate repeats of two types and ribitol and glycerol teichoic acids were isolated from cell wall of Bifidobacterium longum BIM B-476-D by stepwise extraction with 10% CCl3CO2H. The following structures of the glycopolymers were established by sugar analysis, selective cleavage with aq 2% HOAc, dephosphorylation with 48% HF, 2D NMR spectroscopy, and high-resolution ESI MS: [structure: see text]. The ribitol teichoic acid also contains minor D-alanine, whose position was not determined.
structure, teichoic acid, Bifidobacterium longum, glycopolymers
NCBI PubMed ID: 23571164Publication DOI: 10.1016/j.carres.2013.03.006Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: E.L. Zdorovenko
mail.ru>
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, 220141 Minsk, Belarus, Institute of Microbiology, National Academy of Sciences of Belarus, 220141 Minsk, Belarus
Methods: 13C NMR, 1H NMR, NMR-2D, HF solvolysis, sugar analysis, ESI-MS, GLC, mild acid hydrolysis, NMR-1D
The publication contains the following compound(s):
- 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: 11460
Structure type: oligomer
; 476.1741
Compound class: teichoic acid
Reference(s) to other database(s): GTC:G14520FU
- Compound ID: 11461
|
a-D-Glcp-(1-3)-+ a-D-Glcp-(1-2)-+
| |
a-D-Glcp-(1-2)-D-Rib-ol-(5--P--1)--Rib-ol
|
a-D-Glcp-(1-3)-+ |
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Structure type: oligomer
; 1014.3040
Compound class: teichoic acid
- Compound ID: 11462
Structure type: oligomer
; 254.1002
Compound class: teichoic acid
Reference(s) to other database(s): GTC:G38409FH
- Compound ID: 11463
|
-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: 11464
|
P-4)-b-D-Galp-(1-3)-b-D-Galf-(1-3)-a-D-Glcp-(1-2)-b-D-Galf-(1-6)-a-D-GlcpNAc |
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Structure type: oligomer
; 949.2676
Compound class: cell wall polysaccharide
Reference(s) to other database(s): GTC:G06997QC
- Compound ID: 11465
|
P-4)-b-D-Galp-(1-3)-b-D-Galf-(1-3)-a-D-Glcp-(1-2)-b-D-Galf-(1-6)-b-D-GlcpNAc |
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Structure type: oligomer
; 949.2676
Compound class: cell wall polysaccharide
Reference(s) to other database(s): GTC:G45903UC
- Compound ID: 11466
|
P-4)-b-D-Galp-(1-3)-b-D-Galf-(1-3)-a-D-Glcp-(1-2)-b-D-Galf-(1-6)-D-Glcp |
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Structure type: oligomer
; 908.2410
Compound class: cell wall polysaccharide
Reference(s) to other database(s): GTC:G57683SH
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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
|
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
|
LIP-(1-2)-+ |
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Structure type: oligomer
Compound class: lipoteichoic acid
- Compound ID: 14895
|
LIP-(1-1)-+
|
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)-+
|
LIP-(1-?)-+ |
| |
{{{-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
|
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
|
a-D-Glcp-(1-3)-+ a-D-Glcp-(1-3)-+
| |
{{{-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
|
a-D-Glcp-(1-6)-+
|
-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
|
a-D-Galf-(1-2)-a-L-Rhap-(1-2)-+
|
-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
|
-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)-- |
Show graphically |
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- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: EPS
Reference(s) to other database(s): GTC:G41062KO
- Compound ID: 11607
|
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- |
Show graphically |
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)-+
|
-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- |
Show graphically |
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
|
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)-+ |
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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- |
Show graphically |
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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