The cell walls of two strains of the genus Promicromonospora (phylum Actinobacteria) were found to include non-phosphorylated anionic glycopolymers with pyruvic acid acetals of R-configuration. The cell wall of the type strain P. citrea 665T contains two glycopolymers of the sort, including the Kdn-teichulosonic acid with the repeating unit →6)-α-d-Glcp/→6)-α-d-Glcp3SO3-(1→4)-α-[7,9Pyr]-Kdn-(2→, and the galactan with the repeating unit →3)-α-[4,6Pyr]-d-Galp-2OAc-(1→ . The cell wall of Promicromonospora sp.VKM Ac-1028 contains the teichuronic acid with the repeating unit →6)-α-d-Glcp-(1→4)-β-[2,3Pyr]-d-GlcpA-(1→. The detected glycopolymer structures are reported for the first time. Presented results expand the notion on the diversity of the organic world and on the role of the structures and composition of cell wall polymers in bacterial taxonomy. The glycopolymer structures were established by using a combination of chemical methods, NMR- and IR-spectroscopy, and ESI MS.

pyruvate, teichuronic acid, Galactan, NMR-spectroscopy, Kdn-teichulosonic acid, Promicromonospora

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9
4,3	%xXS?
4	aDGlcp	96.8	71.2	83.3	69.1	71.5	63.7
9	x?Pyr	177.4	102.6	25.7
	aXKdnp	175.0	101.8	37.8	76.6	68.4	72.8	75.9	61.2	67.6


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9
4,3	%xXS?
4	aDGlcp	5.11	3.75	4.54	3.87	4.10	3.68-4.11
9	x?Pyr	-	-	1.51
	aXKdnp	-	-	1.71-2.81	3.68	3.87	3.91	3.88	4.04	3.59-4.04


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7	C8/H8	C9/H9
4,3	%xXS?
4	aDGlcp	96.8/5.11	71.2/3.75	83.3/4.54	69.1/3.87	71.5/4.10	63.7/3.68-4.11
9	x?Pyr			25.7/1.51
	aXKdnp			37.8/1.71-2.81	76.6/3.68	68.4/3.87	72.8/3.91	75.9/3.88	61.2/4.04	67.6/3.59-4.04

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

[*]OC[C@H]1O[C@H](O[C@H]2C[C@]([*])(C(=O)O)O[C@@H]([C@@H]3OC(C)(C(=O)O)OC[C@H]3O)[C@@H]2O)[C@H](O)[C@@H](OS(=O)(=O)O)[C@@H]1O

562.455 g/mol (C₁₈H₂₆R₂O₁₈S, R = next and previous repeats, not counted in mol weight)