The subject of the present review is the structural diversity and abundance of cell wall teichuronic and teichulosonic acids of representatives of the order Actinomycetales. Recently found teichulosonic acids are a new class of natural glycopolymers with ald-2-ulosonic acid residues: Kdn (3-deoxy-D-glycero-D-galacto-non-2-ulosonic acid) or di-N-acyl derivatives of Pse (5,7-diamino-3,5,7,9-tetradeoxy-L-glycero-L-manno-non-2-ulosonic or pseudaminic acid) as the obligatory component. The structures of teichuronic and teichulosonic acids are presented. Data are summarized on the occurrence of the glycopolymers of different nature in the cell wall of the studied actinomycetes. The biological role of the glycopolymers and their possible taxonomic implication are discussed. The comprehensive tables given in the Supplement show (13)C NMR spectroscopic data of teichuronic and teichulosonic acids obtained by the authors.
NCBI PubMed ID: 21999534Publication DOI: 10.1134/S0006297911070030Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: em_tulskaya

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Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, All-Russian Collection of Microorganisms (VKM), Skryabin Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, Pushchino, Russia, Lomonosov Moscow State University, Russia, Biological Faculty, Lomonosov Moscow State University, Moscow, Russia
Methods: NMR, ESI-MS, MALDI-TOF MS
- Compound ID: 9882
|
-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
Compound class: teichuronic acid
Reference(s) to other database(s): GTC:G66271HF, CCSD:
45265, CBank-STR:9965
- Compound ID: 9883
|
30%b-D-GlcpNAc-(1-3)-+ S-Pyr-(2-6:2-4)-a-D-ManpNAc-(1-4)-+
| |
-4)-b-D-ManpNAcA-(1-3)-b-D-GlcpN(30%)Ac-(1-6)-a-D-GlcpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: teichuronic acid
- Compound ID: 8706
Structure type: polymer chemical repeating unit
Trivial name: mannan, neutral mannan, BCG-PSN (Bacillus Calmette-Guérin polysaccharide and nucleic acid), α-mannan
Compound class: cell wall polysaccharide
Reference(s) to other database(s): GTC:G75213RY, GlycomeDB:
16270, CCSD:
4940, CBank-STR:4613
- Compound ID: 9890
|
55%a-D-Galp2(33%)Me3Me-(1-4)-+
|
-4)-4HOBut-(1-7)-b-Psep5Ac-(2- |
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Structure type: polymer chemical repeating unit
; n=20-40
Compound class: teichulosonic acid
- Compound ID: 9886
|
b-D-Galp3(33%)Me-(1-9)-+
|
b-D-Galp3(33%)Me-(1-9)-a-Kdnp-(2-4)-b-Kdnp |
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Structure type: oligomer
Compound class: teichulosonic acid
Reference(s) to other database(s): GTC:G90106AF
- Compound ID: 9891
|
?%a-D-Galp2(%)Me3Me-(1-4)-+
|
-3)-b-D-Galp-(1-4)-4HOBut-(1-7)-b-Psep5Ac-(2- |
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Structure type: structural motif or average structure
; n=20-40
Compound class: teichulosonic acid
- Compound ID: 9892
Structure type: structural motif or average structure
; n=20-40
Compound class: teichulosonic acid
- Compound ID: 9893
|
/Variants 0/-+
|
-3)-b-D-Galp-(1-4)-4HOBut-(1-7)-b-Psep5Ac-(2-
/Variants 0/ is:
?%b-L-Rhap-(1-4)-
OR (exclusively)
?%a-D-Galp2(%)Me3Me-(1-4)- |
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Structure type: structural motif or average structure
; n=20-40
Compound class: teichulosonic acid
- Compound ID: 9874
Structure type: polymer chemical repeating unit
; n=8-15
Compound class: teichuronic acid
Reference(s) to other database(s): GTC:G50447ND
- Compound ID: 9887
Structure type: polymer chemical repeating unit
; n>20
Compound class: teichulosonic acid
Reference(s) to other database(s): GTC:G67638CH
- Compound ID: 9875
Structure type: polymer chemical repeating unit
; n=8-15
Compound class: teichuronic acid
Reference(s) to other database(s): GTC:G02048AA
- Compound ID: 9876
|
/Variants 0/-+
|
-4)-b-D-ManpNAc3NA-(1-3)-a-D-GalpNAc-(1-
/Variants 0/ is:
L-Glu-(1-3)-
OR (exclusively)
Ac-3)- |
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Structure type: polymer chemical repeating unit
; n=8-15
Compound class: teichuronic acid
- Compound ID: 9877
Structure type: polymer chemical repeating unit
; n=8-15
Compound class: teichuronic acid
Reference(s) to other database(s): GTC:G27479ZR
- Compound ID: 9878
Structure type: polymer chemical repeating unit
; n=8-15
Compound class: teichuronic acid
Reference(s) to other database(s): GTC:G25067AZ
- Compound ID: 9879
Structure type: polymer chemical repeating unit
; n=8-15
Compound class: teichuronic acid
Reference(s) to other database(s): GTC:G36082FK
- Compound ID: 9880
Structure type: polymer chemical repeating unit
; n=8-15
Compound class: teichuronic acid
Reference(s) to other database(s): GTC:G46629FZ
- Compound ID: 9881
Structure type: polymer chemical repeating unit
; n=8-15
Compound class: teichuronic acid
Reference(s) to other database(s): GTC:G89371DD
- Compound ID: 9884
Structure type: polymer chemical repeating unit
; n>20
Compound class: teichulosonic acid
Reference(s) to other database(s): GTC:G17874CB
- Compound ID: 9885
Structure type: polymer chemical repeating unit
; n>20
Compound class: teichulosonic acid
Reference(s) to other database(s): GTC:G91121EF
- Compound ID: 9896
Structure type: polymer chemical repeating unit
Trivial name: poly(glycosyl 1-phosphate)
Compound class: cell wall polysaccharide
Reference(s) to other database(s): GTC:G18688YV
- Compound ID: 8657
Structure type: polymer chemical repeating unit
Trivial name: teichoic acid
Compound class: cell wall polysaccharide, teichoic acid
Reference(s) to other database(s): GTC:G59594KF
- Compound ID: 9888
Structure type: polymer chemical repeating unit
; n>20
Compound class: teichulosonic acid
Reference(s) to other database(s): GTC:G61706LV
- Compound ID: 9897
Structure type: polymer chemical repeating unit
Trivial name: poly(glycosyl 1-phosphate)
Compound class: cell wall polysaccharide
Reference(s) to other database(s): GTC:G02823KT
- Compound ID: 9889
Structure type: polymer chemical repeating unit
; n>20
Compound class: teichulosonic acid
Reference(s) to other database(s): GTC:G91010VS
- Compound ID: 9894
|
80%a-D-Galp-(1-4)-+
|
-3)-b-D-Glcp-(1-4)-3,4HOBut-(1-7)-b-Psep5Ac-(2- |
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Structure type: structural motif or average structure
; n=20-40
Compound class: teichulosonic acid
- Compound ID: 9895
Structure type: structural motif or average structure
; n=20-40
Compound class: teichulosonic acid