The cell wall of Lactobacillus plantarum contains large amounts of cell wall teichoic acid (WTA). WTA was isolated from the cell wall of L. plantarum NRIC 1068 (= ATCC 8014 and 17-5) by extraction with trichloroacetic acid, and two monomeric units (F1 and F2) were prepared from the alkaline hydrolysate of WTA. Componential analysis by HPLC showed that these monomers were composed of ribitol, glucose, and phosphoric acid. Structural analyses of the monomers were performed by NMR spectroscopy with comparison to chemically synthesized monomers. The structures of F1 and F2 were determined to be 3,4-α-D-diglucosyl-2-phosphoryl ribitol and 3,4-α-D-diglucosyl-1-phosphoryl ribitol respectively. The unique structure of WTA in L. plantarum results from modification of the main chain with multiple glucose residues.

teichoic acid, Lactobacillus plantarum, cell wall structure of lactic acid bacteria

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
3	aDGlcp	100.75	72.25	73.44	70.19	73.36	61.19
4	aDGlcp	98.61	72.34	73.65	70.22	72.66	61.08
	xDRib-ol	63.29	71.45	80.59	80.20	62.38


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
3	aDGlcp	5.08	3.55	3.66	3.43	3.84	3.78-3.86
4	aDGlcp	5.18	3.56	3.75	3.44	3.87	3.77-3.82
	xDRib-ol	3.78-3.85	4.03	3.93	4.07	3.82-3.84


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
3	aDGlcp	100.75/5.08	72.25/3.55	73.44/3.66	70.19/3.43	73.36/3.84	61.19/3.78-3.86
4	aDGlcp	98.61/5.18	72.34/3.56	73.65/3.75	70.22/3.44	72.66/3.87	61.08/3.77-3.82
	xDRib-ol	63.29/3.78-3.85	71.45/4.03	80.59/3.93	80.20/4.07	62.38/3.82-3.84

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

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

476.428 g/mol (C₁₇H₃₂O₁₅)

The cell wall of Lactobacillus plantarum contains large amounts of cell wall teichoic acid (WTA). WTA was isolated from the cell wall of L. plantarum NRIC 1068 (= ATCC 8014 and 17-5) by extraction with trichloroacetic acid, and two monomeric units (F1 and F2) were prepared from the alkaline hydrolysate of WTA. Componential analysis by HPLC showed that these monomers were composed of ribitol, glucose, and phosphoric acid. Structural analyses of the monomers were performed by NMR spectroscopy with comparison to chemically synthesized monomers. The structures of F1 and F2 were determined to be 3,4-α-D-diglucosyl-2-phosphoryl ribitol and 3,4-α-D-diglucosyl-1-phosphoryl ribitol respectively. The unique structure of WTA in L. plantarum results from modification of the main chain with multiple glucose residues.

teichoic acid, Lactobacillus plantarum, cell wall structure of lactic acid bacteria

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
3	aDGlcp	100.53	72.22	73.42	70.13	73.36	61.17
2	P
4	aDGlcp	98.70	72.48	73.64	70.20	72.63	61.05
	xDRib-ol	61.77	76.14	78.85	79.98	62.32


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
3	aDGlcp	5.18	3.55	3.67	3.43	3.84	3.79-3.88
2	P
4	aDGlcp	5.19	3.54	3.77	3.43	3.89	3.79-3.83
	xDRib-ol	3.95-3.96	4.47	4.17	4.10	3.84-3.86


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
3	aDGlcp	100.53/5.18	72.22/3.55	73.42/3.67	70.13/3.43	73.36/3.84	61.17/3.79-3.88
2	P
4	aDGlcp	98.70/5.19	72.48/3.54	73.64/3.77	70.20/3.43	72.63/3.89	61.05/3.79-3.83
	xDRib-ol	61.77/3.95-3.96	76.14/4.47	78.85/4.17	79.98/4.10	62.32/3.84-3.86

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

O=P(O)(O)O[C@@H](CO)[C@H](O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@@H](CO)O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

556.407 g/mol (C₁₇H₃₃O₁₈P)

The cell wall of Lactobacillus plantarum contains large amounts of cell wall teichoic acid (WTA). WTA was isolated from the cell wall of L. plantarum NRIC 1068 (= ATCC 8014 and 17-5) by extraction with trichloroacetic acid, and two monomeric units (F1 and F2) were prepared from the alkaline hydrolysate of WTA. Componential analysis by HPLC showed that these monomers were composed of ribitol, glucose, and phosphoric acid. Structural analyses of the monomers were performed by NMR spectroscopy with comparison to chemically synthesized monomers. The structures of F1 and F2 were determined to be 3,4-α-D-diglucosyl-2-phosphoryl ribitol and 3,4-α-D-diglucosyl-1-phosphoryl ribitol respectively. The unique structure of WTA in L. plantarum results from modification of the main chain with multiple glucose residues.

teichoic acid, Lactobacillus plantarum, cell wall structure of lactic acid bacteria

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
0,3	aDGlcp	100.66	72.02	73.12	70.08	73.18	61.5
0,4	aDGlcp	98.42	72.02	73.42	70.08	72.45	60.91
0	xDRib-ol	66.57	70.08	79.59	80.15	62.39
	P


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
0,3	aDGlcp	5.10	3.55	3.64	3.41	3.84	3.76-3.85
0,4	aDGlcp	5.20	3.55	3.75	3.42	3.86	3.75-3.80
0	xDRib-ol	4.08-4.12	4.13	3.95	4.10	3.82-3.82
	P


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
0,3	aDGlcp	100.66/5.10	72.02/3.55	73.12/3.64	70.08/3.41	73.18/3.84	61.5/3.76-3.85
0,4	aDGlcp	98.42/5.20	72.02/3.55	73.42/3.75	70.08/3.42	72.45/3.86	60.91/3.75-3.80
0	xDRib-ol	66.57/4.08-4.12	70.08/4.13	79.59/3.95	80.15/4.10	62.39/3.82-3.82
	P

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

O=P(O)(O)OC[C@H](O)[C@H](O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@@H](CO)O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

556.407 g/mol (C₁₇H₃₃O₁₈P)