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1. (Article ID: 5216)
Shit P, Misra AK
Synthesis of a hexasaccharide repeating unit of the cell wall polysaccharide of Bifidobacterium animalis subsp. lactis LKM512
Carbohydrate Research 473 (2019)
12-17
A convergent synthesis of the hexasaccharide as its 2-aminoethyl glycoside corresponding to the repeating unit of the cell wall polysaccharide of Bifidobacterium animalis subsp. lactis LKM512 has been achieved applying a [4 + 2] glycosylation strategy. The disaccharide thioglycoside donor was prepared by combining a d-galactofuranosyl thioglycoside with another l-rhamnosyl thioglycoside acceptor. The yields of the individual glycosylation steps were highly satisfactory with excellent stereo outcome. An ?-glycosidic linkage of the d-galactofuranosyl moiety in the hexasaccharide was achieved in very good yield.
Oligosaccharides, cell wall, glycosylation, Bifidobacterium animalis, HClO(4)-SiO(2), probiotics
NCBI PubMed ID: 30599388Publication DOI: 10.1016/j.carres.2018.12.014Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: akmisra69
gmail.com
Institutions: Bose Institute, Division of Molecular Medicine, P-1/12, C.I.T. Scheme VII-M, Kolkata, 700054, India
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, MALDI-MS, chemical synthesis, chemical methods, glycosylation, optical rotation measurement
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
|
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)-+
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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)-+
| |
{{{-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
|
-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
|
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- |
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)-+ |
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- |
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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