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	aDGlcp	99.7	72.9	74.5	71.0	73.3	62.0
	x?Gro	70.0	71.9	63.9


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
1	aDGlcp	4.93	3.57	3.74	3.42	3.68	3.77-3.87
	x?Gro	3.59-3.78	3.96	3.66-3.70


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
1	aDGlcp	99.7/4.93	72.9/3.57	74.5/3.74	71.0/3.42	73.3/3.68	62.0/3.77-3.87
	x?Gro	70.0/3.59-3.78	71.9/3.96	63.9/3.66-3.70

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)