Cell walls of Bacillus subtilis VKM B-760 and VKM B-764 are characterized by heterogeneous composition of teichoic acids. Polymer I with structure -6)-β-D-Galp-(1→1)-sn-Gro-(3-P-, polymer II with structure -6)-α-D-Glcp-(1→1)-sn-Gro-(3-P-, and a small amount of unsubstituted 1,3-poly(glycerol phosphate) were detected in strain VKM B-760. Strain VKM B-764 contains an analogous set of teichoic acids, but a characteristic feature of polymer II is the presence of disubstituted glycerol residue with α-glucopyranose localization in the integral chain at C-1 hydroxyl and β-glucopyranose as a side branch at C-2 hydroxyl (polymer III): -6)-α-D-Glcp-(1→1)-[β-D-Glcp-(1→2)]-sn-Gro-(3-P-. The structures of polymer I in bacilli and polymer III in Gram-positive bacteria are described for the first time. Teichoic acids were studied by chemical methods and on the basis of combined analysis of one-dimensional 1H-, 13C-, and (31)P-NMR spectra, homonuclear two-dimensional (1)H/(1)H COSY, TOCSY, and ROESY, and heteronuclear two-dimensional (1)H/(13)C gHSQC- and HMQC-TOCSY experiments. Simultaneous presence of several different structure teichoic acids in the bacillus cell walls as well as chemotaxonomical perspectives of the application of these polymers as species-specific markers for members of the Bacillus genus is discussed.

NMR spectroscopy, cell wall, teichoic acids, Bacillus subtilis

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
1	bDGalp	104.8	72.3	74.1	70.1	76.6	62.5
	x?Gro	72.4	72.2	63.8


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
1	bDGalp	4.42	3.56	3.67	3.93	3.71	3.77-3.79
	x?Gro	3.69-4.01	3.95	3.63-3.71


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
1	bDGalp	104.8/4.42	72.3/3.56	74.1/3.67	70.1/3.93	76.6/3.71	62.5/3.77-3.79
	x?Gro	72.4/3.69-4.01	72.2/3.95	63.8/3.63-3.71

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

OCC(O)CO[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O

254.235 g/mol (C₉H₁₈O₈)