Lipoteichoic acids were isolated from four tyoe strains belonging to the genus Agromyces. The structure of lipoteichoic acids, which was established chemically and by 13C-NMR spectroscopy, was similar in all four strains. The hydrophilic part of these acids was represented by 1.3-poly(glycerolphosphate) carrying a-galactopyranosyl and O-acetyl substituents at the C-2 position of glycerol. O-acetyl substituents in lipoteichoic acids were discovered for the first time. The quantity of substituents in the four lipoteichoic acids was different. In the hydrophobic part, predominating fatty acids were anteiso-pentadecanoic, iso-hexadecanoic, and anteiso-hexadecanoic, and also n-octadecanoic in the case of A. fucosus ssp. fucosus and A. fucosus ssp. hippuratus.
Journal NLM ID: 0376652Publisher: Moskva: Izdatelstvo Nauka
Institutions: M.V. Lomonosov State University, Moscow, Russia, Institute of Biochemistry and Physiology of Microorganisms, Pushchino, Russia
Methods: 13C NMR, gel filtration, sugar analysis, acid hydrolysis, paper chromatography, electrophoresis, alkaline hydrolysis
Information on the prevalence, compositions, and structures of anionic carbohydrate-containing polymers of cell walls of Gram-positive bacteria is summarized. The data suggest that these polymers are important for normal functioning of bacterial cells and require further studies. Structural data on teichoic acids found in the literature published over the last few years are discussed. This is a very diverse class of polymers whose structure-specific pathways of degradation were studied and NMR spectra were examined. Unique comprehensive tables of 13C-NMR spectroscopic data (mainly obtained by the authors) on these polymers are given in the Appendix. Other tables summarize data on teichuronic acids, sugar-phosphate polymers, acid polysaccharides, and structural variants of bonds between acid polysaccharides and peptidoglycans known from the literature. Functions of anionic polymers and their possible chemotaxonomic applications are discussed
- Compound ID: 1034
|
a-L-Rhap-(1-2)-+
|
-6)-a-D-GalpNAc-(1-3)-b-L-Rhap-(1-4)-b-D-Glcp-(1-6)-b-D-Galf-(1-6)-b-D-Galp-(1-3)-a-D-GalpNAc-(1-P- |
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Structure type: polymer chemical repeating unit
Trivial name: poly(glycosyl phosphate)
Compound class: CPS, cell wall polysaccharide
Reference(s) to other database(s): GTC:G54118ZE, GlycomeDB:
16673
- Compound ID: 8345
|
Cho-(1--P--6)--+ Cho-(1--P--6)--+
| |
-6)-b-D-Glcp-(1-3)-a-D-FucpNAc4N-(1-4)-a-D-GalpNAc-(1-3)-b-D-GalpNAc-(1-1)-Rib-ol-(5-P- |
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Structure type: polymer chemical repeating unit
Trivial name: C polysaccharide, zwitterionic polysaccharide (ZPSs)
Compound class: cell wall polysaccharide, teichoic acid
- Compound ID: 11016
Structure type: polymer chemical repeating unit
Trivial name: poly(glycosyl phosphate)
Compound class: cell wall polysaccharide
Reference(s) to other database(s): GTC:G02591RD
- Compound ID: 7476
|
-6)-a-D-GalpNAc-(1-3)-b-L-Rhap-(1-4)-b-D-Glcp-(1-6)-b-D-Galf-(1-6)-b-D-GalpNAc-(1-3)-a-D-Galp-(1-P- |
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Structure type: polymer chemical repeating unit
Trivial name: poly(glycosyl phosphate)
Compound class: cell wall polysaccharide
Reference(s) to other database(s): GTC:G54207VN, GlycomeDB:
34752
- Compound ID: 11011
|
a-Rhap-(1-2)-+
|
-6)-a-D-GalpNAc-(1-3)-b-L-Rhap-(1-4)-b-D-Glcp-(1-6)-b-D-Galf-(1-6)-b-D-GalpNAc-(1-3)-a-D-Galp-(1-P- |
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Structure type: polymer chemical repeating unit
Trivial name: poly(glycosyl phosphate)
Compound class: cell wall polysaccharide
Reference(s) to other database(s): GTC:G95962IT
- Compound ID: 2295
|
-6)-b-D-Galf-(1-3)-b-D-Galp-(1-6)-b-D-Galf-(1-6)-b-D-GalpNAc-(1-3)-a-D-Galp-(1-1)-D-Rib-ol-(5-P- |
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Structure type: polymer chemical repeating unit
Trivial name: coaggregation receptor polysaccharide (RPS)
Compound class: cell wall polysaccharide, teichoic acid
Reference(s) to other database(s): GTC:G42952EF, GlycomeDB:
38085
- Compound ID: 4520
|
-4)-b-D-GlcpA-(1-4)-b-D-GlcpA-(1-3)-b-D-GalpNAc-(1-6)-a-D-GalpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: teichuronic acid
Reference(s) to other database(s): GTC:G24167ZQ, GlycomeDB:
2566
- Compound ID: 4521
|
-4)-b-D-Glcp-(1-4)-b-D-Glcp-(1-3)-b-D-GalpNAc-(1-6)-a-D-GalpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: teichuronic acid, reduced teichuronic acid
Reference(s) to other database(s): GTC:G50246UY, GlycomeDB:
2566
- Compound ID: 9792
Structure type: polymer chemical repeating unit
Trivial name: teichoic acid
Compound class: CPS, cell wall polysaccharide, teichoic acid
Reference(s) to other database(s): GTC:G75800OJ
- Compound ID: 9793
Structure type: polymer chemical repeating unit
Trivial name: teichoic acid
Compound class: cell wall polysaccharide, teichoic acid
Reference(s) to other database(s): GTC:G66422PP
- Compound ID: 10971
Structure type: homopolymer
Trivial name: teichoic acid
Compound class: cell wall polysaccharide, teichoic acid
Reference(s) to other database(s): GTC:G09659CF
- Compound ID: 10981
Structure type: fragment of a bigger structure
Compound class: teichoic acid
Reference(s) to other database(s): GTC:G09999PO
- Compound ID: 10982
Structure type: fragment of a bigger structure
Compound class: teichoic acid
Reference(s) to other database(s): GTC:G03310MH
- Compound ID: 10983
Structure type: polymer chemical repeating unit
Compound class: teichoic acid
Reference(s) to other database(s): GTC:G27289XG
- Compound ID: 11013
|
a-L-Rhap-(1-3)-+
|
-6)-b-D-Galp-(1-6)-a-D-Galp-(1-3)-b-L-Rhap-(1-4)-b-D-Glcp-(1-4)-a-D-GlcpNAc-(1-2)-a-D-Glcp-(1-P-
|
b-D-Glc-(1-6)-+ |
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Structure type: polymer chemical repeating unit
Trivial name: poly(glycosyl phosphate)
Compound class: cell wall polysaccharide
Reference(s) to other database(s): GTC:G73652RG
- Compound ID: 11012
|
-6)-a-D-Galp-(1-3)-b-L-Rhap-(1-4)-b-D-Glcp-(1-6)-b-D-Galf2(33%)Ac-(1-6)-b-D-Galp-(1-3)-a-D-GalpNAc6(33%)Ac-(1-P- |
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Structure type: polymer chemical repeating unit
Trivial name: poly(glycosyl phosphate)
Compound class: cell wall polysaccharide
Reference(s) to other database(s): GTC:G09089VL
- Compound ID: 10985
|
a-L-Rhap-(1-3)-a-L-Rhap-(1-3)-b-L-GlcpNAc-(1-2)-a-L-Rhap-(1-4)-+
|
-1)-Rib-ol-(5-P- |
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Structure type: polymer chemical repeating unit
; n=12-13
Compound class: teichoic acid
Reference(s) to other database(s): GTC:G93104UW
- Compound ID: 10988
Structure type: polymer chemical repeating unit
Compound class: teichoic acid
Reference(s) to other database(s): GTC:G11566TK
- Compound ID: 11004
|
Gro-(1--50%P--6)--b-D-Glcp-(1-3)-+
|
-6)-/Variants 0/-b-D-ManpNAcA-(1-4)-b-D-GlcpNAc-(1-
/Variants 0/ is:
a-D-Glcp-(1-4)-
OR (exclusively)
a-D-Glcp-(1-3)- |
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Structure type: polymer chemical repeating unit
; n=12-15
Compound class: teichuronic acid
- Compound ID: 11015
Structure type: polymer chemical repeating unit
Trivial name: poly(glycosyl phosphate), secondary cell wall polymer (SCWP)
Compound class: cell wall polysaccharide
- Compound ID: 7258
Structure type: polymer chemical repeating unit
; n=12
Trivial name: repeating unit, poly(glycosyl phosphate)
Compound class: cell wall polysaccharide
Reference(s) to other database(s): GTC:G68056ED, GlycomeDB:
34744
- Compound ID: 7302
|
-6)-a-D-Glcp-(1-4)-b-D-GlcpNAc3NAcA-(1-4)-a-D-GlcpNAc3NAc-(1-4)-b-D-ManpNAc3NAcA-(1- |
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Structure type: polymer chemical repeating unit
; n=6
Compound class: teichuronic acid
Reference(s) to other database(s): GTC:G66271HF, GlycomeDB:
3793, CCSD:
33408, CBank-STR:8759
- Compound ID: 7460
Structure type: polymer chemical repeating unit
Trivial name: poly(glycosyl phosphate)
Compound class: cell wall polysaccharide
Reference(s) to other database(s): GTC:G65288VY, GlycomeDB:
34739
- Compound ID: 11010
Structure type: homopolymer
Trivial name: poly(glycosyl phosphate)
Compound class: cell wall polysaccharide
Reference(s) to other database(s): GTC:G16695BT
- Compound ID: 10828
Structure type: polymer chemical repeating unit
Trivial name: poly(glycosyl phosphate), glycosyl 1-phosphate polymer (GPP)
Compound class: cell wall polysaccharide
Reference(s) to other database(s): GTC:G04691MX
- Compound ID: 10990
Structure type: polymer chemical repeating unit
; n=23
Compound class: teichoic acid
Reference(s) to other database(s): GTC:G54098RG
- Compound ID: 10995
Structure type: polymer chemical repeating unit
Compound class: teichoic acid
Reference(s) to other database(s): GTC:G37685YG
- Compound ID: 9787
Structure type: polymer chemical repeating unit
Trivial name: teichoic acid
Compound class: cell wall polysaccharide, teichoic acid
Reference(s) to other database(s): GTC:G86229HG
- Compound ID: 11017
|
-6)-b-D-Glcp-(1-6)-b-D-Galp-(1-6)-/Variants 0/-Gro-(2-P-
/Variants 0/ is:
a-D-Glcp-(1-3)-
OR (exclusively)
a-D-Glcp-(1-1)- |
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Structure type: polymer chemical repeating unit
Compound class: cell wall polysaccharide
- Compound ID: 10055
Structure type: polymer chemical repeating unit
Compound class: teichoic acid
Reference(s) to other database(s): GTC:G12307DR, CCSD:
3676, CBank-STR:11241
- Compound ID: 10973
Structure type: polymer chemical repeating unit
Compound class: teichoic acid
Reference(s) to other database(s): GTC:G34526NV
- Compound ID: 10974
Structure type: polymer chemical repeating unit
Compound class: teichoic acid
Reference(s) to other database(s): GTC:G07162BP
- Compound ID: 10993
|
Gro-(3--P--3)--+
|
-6)-b-D-Galp-(1-3)-Gro-(1--P--6)--b-D-Galp-(1-1)-Gro-(3-P- |
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Structure type: polymer chemical repeating unit
Compound class: teichoic acid
Reference(s) to other database(s): GTC:G12307DR
- Compound ID: 10991
Structure type: oligomer
Compound class: teichoic acid
Reference(s) to other database(s): GTC:G99812DJ
- Compound ID: 10992
Structure type: oligomer
Compound class: teichoic acid
Reference(s) to other database(s): GTC:G12307DR
- Compound ID: 10972
Structure type: homopolymer
Trivial name: teichoic acid, teichoic acid (TA)
Compound class: cell wall polysaccharide, teichoic acid
Reference(s) to other database(s): GTC:G71097MN
- Compound ID: 10975
|
a-D-GlcpN-(1-2)-+
|
L-Lys-(1-2)-+ | a-D-GlcpNAc-(1-2)-+
| | |
---P--1)-Gro-(3--P--1)--Gro-(3--P--1)--Gro-(3--P--1)--Gro-(3--P--1)--Gro-(3- |
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Structure type: polymer chemical repeating unit
Compound class: teichoic acid
- Compound ID: 10976
Structure type: fragment of a bigger structure
Compound class: teichoic acid
Reference(s) to other database(s): GTC:G52500FR
- Compound ID: 10977
Structure type: fragment of a bigger structure
Compound class: teichoic acid
- Compound ID: 9778
Structure type: polymer chemical repeating unit
Trivial name: poly(glycosyl 1-phosphate)
Compound class: cell wall polysaccharide, teichoic acid
Reference(s) to other database(s): GTC:G00933AQ
- Compound ID: 10978
Structure type: polymer chemical repeating unit
Compound class: teichoic acid
Reference(s) to other database(s): GTC:G91899DF
- Compound ID: 10979
Structure type: polymer chemical repeating unit
; n=50
Compound class: teichoic acid
Reference(s) to other database(s): GTC:G11065PF
- Compound ID: 10980
Structure type: polymer chemical repeating unit
Compound class: teichoic acid
- Compound ID: 10984
|
?%a-L-Rhap-(1--P--4)--+ ?%a-L-Rhap3Me-(1--P--4)--+
| |
-1)-Rib-ol-(5--P--1)--Rib-ol-(5--P--1)--Rib-ol-(5-P- |
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Structure type: polymer chemical repeating unit
; n=20
Compound class: teichoic acid
- Compound ID: 10986
Structure type: homopolymer
Compound class: teichoic acid
Reference(s) to other database(s): GTC:G08338HQ
- Compound ID: 10987
Structure type: polymer chemical repeating unit
Compound class: teichoic acid
- Compound ID: 10989
Structure type: polymer chemical repeating unit
Compound class: teichoic acid
- Compound ID: 10994
Structure type: polymer chemical repeating unit
Compound class: teichoic acid
Reference(s) to other database(s): GTC:G12307DR
- Compound ID: 7412
Structure type: polymer chemical repeating unit
Compound class: teichoic acid
Reference(s) to other database(s): GTC:G97835JZ
- Compound ID: 7413
Structure type: polymer chemical repeating unit
Compound class: teichoic acid
Reference(s) to other database(s): GTC:G89186NG
- Compound ID: 10996
Structure type: polymer chemical repeating unit
Compound class: teichoic acid
Reference(s) to other database(s): GTC:G06597UI
- Compound ID: 10997
|
Suc-(1-3)-+
|
-1)-Gro-(3--P--4)--b-D-GalpNAc-(1-4)-b-D-GalpNAc-(1-2)-Gro-(3-P- |
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Structure type: polymer chemical repeating unit
Compound class: teichoic acid
Reference(s) to other database(s): GTC:G74788VB
- Compound ID: 10999
Structure type: polymer chemical repeating unit
Compound class: teichuronic acid
Reference(s) to other database(s): GTC:G48945EP
- Compound ID: 11001
|
Gro-(1--50%P--6)--b-D-Glcp-(1-6)-+
|
-6)-a-D-Glcp-(1-3)-b-D-ManpNAcA-(1-4)-b-D-GlcpNAc-(1-
|
a-D-Galp-(1-3)-+ |
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Structure type: polymer chemical repeating unit
; n=24-28
Compound class: teichuronic acid
Reference(s) to other database(s): GTC:G79695EM
- Compound ID: 11002
|
a-D-Glcp-(1-3)-+
|
-4)-a-D-GlcpA-(1-3)-a-D-GlcpA-(1-3)-a-D-Glcp-(1-3)-a-D-Fucp-(1- |
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Structure type: polymer chemical repeating unit
; n=85-95
Compound class: teichuronic acid
Reference(s) to other database(s): GTC:G27952LQ
- Compound ID: 11003
|
b-D-GlcpA-(1-3)-+
|
-4)-b-D-Glcp-(1-3)-a-L-Rhap-(1-4)-a-L-Rhap-(1- |
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Structure type: polymer chemical repeating unit
; 500000
Compound class: teichuronic acid
Reference(s) to other database(s): GTC:G32621AR
- Compound ID: 11005
Structure type: polymer chemical repeating unit
Compound class: teichuronic acid
Reference(s) to other database(s): GTC:G51107WG
- Compound ID: 11006
Structure type: polymer chemical repeating unit
; n=25-40
Compound class: teichuronic acid
Reference(s) to other database(s): GTC:G61226GA
- Compound ID: 11007
|
ManpNAcA-(1-4)-ManpNAcA-(1-3)-a-D-GlcpNAc-(1---P---P----/->1)undecaprenol (C55)/ |
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Structure type: oligomer
Aglycon: ->1)undecaprenol (C55)
Trivial name: teichuronic acid
- Compound ID: 11008
|
-6)-a-D-Galp-(1-4)-b-D-ManpNAc3NAcA-(1-6)-a-D-Glcp-(1-4)-b-D-ManpNAc3NAcA-(1-3)-b-D-GalpNAc-(1- |
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Structure type: polymer chemical repeating unit
; n=11
Compound class: teichuronic acid
Reference(s) to other database(s): GTC:G25612XX
- Compound ID: 11009
|
D-GlcpA-(1-4)-+
|
-3)-L-6dTalp-(1-3)-D-Galp-(1-3)-L-Rhap-(1-2)-L-Rhap-(1- |
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Structure type: polymer chemical repeating unit
Compound class: teichuronic acid
Reference(s) to other database(s): GTC:G46356OS
- Compound ID: 10784
Structure type: polymer chemical repeating unit
Trivial name: repeating unit, poly(glycosyl phosphate)
Compound class: cell wall polysaccharide, lipoteichoic acid
- Compound ID: 11014
|
Gro-(1--P--2)--+
|
-4)-a-D-GlcpNAc-(1-3)-a-L-Rhap-(1-3)-a-D-Galp-(1-4)-a-L-Rhap-(1- |
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Structure type: polymer chemical repeating unit
Trivial name: poly(glycosyl phosphate)
Compound class: cell wall polysaccharide
Reference(s) to other database(s): GTC:G31036RN