Department of Bio-Organic Chemistry, Utrecht University, Utrecht, The Netherlands
The capsular polysaccharide of Streptococcus pneumoniae serotype 6B [→2)-α-D-Galp-(1→3)-α-D-Glcp-(1→3)-α-L-Rhap-(1→4)-D-Rib-OH-(5-P→]n was depolymerised under alkaline (NaOH) and acidic (HF) conditions. The former treatment yielded, as the major component, α-2-P-Galp-(1→3)-α-Glcp-(1→3)-α-Rhap-(1→4)-5-P-Rib-OH. The latter treatment at -16 degrees gave α-Galp-(1→3)-α-Glcp-(1→3)-α-Rhap-(1→4)-Rib-OH-(5-P→2)-α-Galp-(1→3)-α-Glcp-(1→3)-α-Rhap-(1→4)-Rib-OH and at 4 degrees gave α-Galp-(1→3)-α-Glcp-(1→3)-α-Rhap-(1→4)-Rib-OH. These oligosaccharides were characterised by sugar analysis, f.a.b.-m.s., and 1H- and 13C-n.m.r. spectroscopy.
13C NMR, 1H NMR, GLC-MS, NMR-2D, sugar analysis, 31P NMR, acid hydrolysis, GLC, alkaline hydrolysis, HF treatment
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
4,3,3,2,0,4,3,3 aDGalp 100.51 69.94 70.65 70.43 71.95 62.10
4,3,3,2,0,4,3 aDGlcp 96.67 71.05-71.44 79.94-80.83 71.05-71.44 72.55-72.74 61.42
4,3,3,2,0,4 aLRhap 101.03 68.15 76.47 71.51 70.65 18.01
4,3,3,2,0 xDRib-ol 63.89 72.59 73.30 78.31 65.82
4,3,3,2 P
4,3,3 aDGalp 98.77 74.36 69.57 70.43 71.59 61.88
4,3 aDGlcp 96.73 71.05-71.44 80.58 71.05-71.44 72.55-72.74 61.42
4 aLRhap 101.03 68.22 76.62 71.51 70.65 18.01
xDRib-ol 63.84 72.84 73.30 79.94-80.83 60.76
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
4,3,3,2,0,4,3,3 aDGalp 5.399 3.838 3.911 4.015 4.259 3.728-3.728
4,3,3,2,0,4,3 aDGlcp 5.153 3.679 3.945 3.725 4.008 3.790-3.790
4,3,3,2,0,4 aLRhap 5.153 4.292 3.886 3.580 3.809 1.310
4,3,3,2,0 xDRib-ol 3.637-3.799 3.787 3.848 4.112 4.122-4.233
4,3,3,2 P
4,3,3 aDGalp 5.623 4.295 4.007 4.066 4.314 3.739-3.739
4,3 aDGlcp 5.118 3.686 3.985 3.692 3.993 3.790-3.790
4 aLRhap 5.077 4.259 3.893 3.588 3.805 1.310
xDRib-ol 3.631-3.791 3.736 3.854 3.943 3.760-3.897
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
4,3,3,2,0,4,3,3 aDGalp 100.51/5.399 69.94/3.838 70.65/3.911 70.43/4.015 71.95/4.259 62.10/3.728-3.728
4,3,3,2,0,4,3 aDGlcp 96.67/5.153 71.05-71.44/3.679 79.94-80.83/3.945 71.05-71.44/3.725 72.55-72.74/4.008 61.42/3.790-3.790
4,3,3,2,0,4 aLRhap 101.03/5.153 68.15/4.292 76.47/3.886 71.51/3.580 70.65/3.809 18.01/1.310
4,3,3,2,0 xDRib-ol 63.89/3.637-3.799 72.59/3.787 73.30/3.848 78.31/4.112 65.82/4.122-4.233
4,3,3,2 P
4,3,3 aDGalp 98.77/5.623 74.36/4.295 69.57/4.007 70.43/4.066 71.59/4.314 61.88/3.739-3.739
4,3 aDGlcp 96.73/5.118 71.05-71.44/3.686 80.58/3.985 71.05-71.44/3.692 72.55-72.74/3.993 61.42/3.790-3.790
4 aLRhap 101.03/5.077 68.22/4.259 76.62/3.893 71.51/3.588 70.65/3.805 18.01/1.310
xDRib-ol 63.84/3.631-3.791 72.84/3.736 73.30/3.854 79.94-80.83/3.943 60.76/3.760-3.897
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