The particulate enzyme from Bacillus subtilis AHU 1031 catalyzed the synthesis of a polysaccharide and glycolipids from UDP-N-acetylmannosaminuronic acid (UDP-ManNAcUA), UDP-N-acetylglucosamine (UDP-GlcNAc), and UDP-glucose (UDP-Glc). The polysaccharide synthesis required UDP-ManNAcUA and UDP-GlcNAc, proceeded optimally at pH 8.5 and in the presence of 5 mM MgCl2 and 2.5 mM dithiothreitol, and was stimulated by the addition of UDP-Glc. The molar ratio of ManNAcUA, GlcNAc, and Glc incorporated into polysaccharide was calculated to be 1:1:1.8 from chemical analysis involving reduction with water soluble carbodiimide; its relative molecular mass was estimated to be 12000. The analysis of Smith degradation products revealed that the polysaccharide backbone is composed of repeating trisaccharide units comprising ManNAcUA, GlcNAc, and Glc. Based on the data regarding the time course of the incorporation of glucose into the polysaccharide, extra glucose seems to be attached to the polysaccharide backbone as lateral branches. The saccharide moieties of the glycolipids were identified as GlcNAc, ManNAcUA-GlcNAc, and Glc-ManNAcUA-GlcNAc from several analytical criteria. The addition of antibiotic 24010, a tunicamycin-like antibiotic, at 10 micrograms/ml resulted in almost complete inhibition of the synthesis of glycolipids and polysaccharide. It is therefore concluded that the glycolipids function as intermediates in polysaccharide formation. Incubation of the ManNAcUA-GlcNAc-linked lipid. (labeled in the ManNAcUA moiety) with the particulate enzyme and UDP-Glc resulted incorporation of radioactivity into a trisaccharide-linked lipid and a polysaccharide. These results suggest that the particulate enzyme utilizes the trisaccharide moiety of the Glc-ManNAcUA-GlcNAc-linked lipid for the elongation of the main polysaccharide chain presumed to be cell wall acidic polysaccharide of this strain.
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