A.A. Parhomchuk <lina_chuk
N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
The O-polysaccharide was obtained by mild acid degradation of the lipopolysaccharide of Providencia alcalifaciens O12. Its structure was studied by sugar analysis using GLC of the alditol acetates and (S)-2-octyl glycosides, methylation analysis, Smith degradation, and (1)H and (13)C NMR spectroscopy, including 2D (1)H-(1)H COSY, TOCSY, ROESY, (1)H-(13)C HSQC, and HMBC experiments. It was found that the polymer is a neutral heteropolysaccharide and has a branched heptasaccharide repeating unit with the following structure: (formula, see text).
13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, sugar analysis, ESI-MS, GLC, mild acid hydrolysis, Smith degradation
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,4,3,2,2,2 Ac
3,4,3,2,2 bDGlcpN 105.1 57.8 74.7 71.9 77.0 62.0
3,4,3,2 bDGlcp 102.4 85.0 78.4 71.6 77.4 62.7
3,4,3,3,2 Ac
3,4,3,3 bDGlcpN 102.6 57.8 75.2 71.9 77.7 62.2
3,4,3 bDGalp 104.2 77.9 81.6 76.2 76.9 62.4
3,4,2 Ac
3,4 aDGalpN 99.9 50.4 78.0 69.8 71.9 62.0
3 bDGalp 106.3 72.2 73.6 78.4 75.2 61.9
2 Ac
bDGalpN 102.6 52.3 82.1 70.0 76.4 62.5
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,4,3,2,2,2 Ac
3,4,3,2,2 bDGlcpN 4.63 3.77 3.63 3.44 3.43 3.80-3.92
3,4,3,2 bDGlcp 4.42 3.28 3.38 3.31 3.05 3.83
3,4,3,3,2 Ac
3,4,3,3 bDGlcpN 5.09 3.90 3.77 3.47 3.40 3.78-3.92
3,4,3 bDGalp 4.62 3.51 4.15 4.38 3.77 3.73-3.76
3,4,2 Ac
3,4 aDGalpN 4.92 4.30 4.06 4.27 4.40 3.72
3 bDGalp 4.64 3.59 3.73 3.99 3.77 3.71
2 Ac
bDGalpN 4.97 4.18 3.93 4.18 3.69 3.79-3.82
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,4,3,2,2,2 Ac
3,4,3,2,2 bDGlcpN 105.1/4.63 57.8/3.77 74.7/3.63 71.9/3.44 77.0/3.43 62.0/3.80-3.92
3,4,3,2 bDGlcp 102.4/4.42 85.0/3.28 78.4/3.38 71.6/3.31 77.4/3.05 62.7/3.83
3,4,3,3,2 Ac
3,4,3,3 bDGlcpN 102.6/5.09 57.8/3.90 75.2/3.77 71.9/3.47 77.7/3.40 62.2/3.78-3.92
3,4,3 bDGalp 104.2/4.62 77.9/3.51 81.6/4.15 76.2/4.38 76.9/3.77 62.4/3.73-3.76
3,4,2 Ac
3,4 aDGalpN 99.9/4.92 50.4/4.30 78.0/4.06 69.8/4.27 71.9/4.40 62.0/3.72
3 bDGalp 106.3/4.64 72.2/3.59 73.6/3.73 78.4/3.99 75.2/3.77 61.9/3.71
2 Ac
bDGalpN 102.6/4.97 52.3/4.18 82.1/3.93 70.0/4.18 76.4/3.69 62.5/3.79-3.82