Department of Veteran Affairs Medical Center, 500 Foothill Boulevard (151), 84148, Salt Lake City, UT, USA, Departments of Pathology and Biochemistry, Uni6ersity of Utah, Salt Lake City, UT 84148, USA, Consiglio Nazionale delle Ricerche, Istituto per la Chimica e la Tecnologia dei Materiali Polimerici, 6.le A. Doria, 6 -95125 Catania, Italy
The exopolysaccharide produced by a cystic fibrosis clinical isolate of Agrobacterium radiobacter was shown by monosaccharide and methylation analyses, degradation with succinoglycanase and NMR analysis to be a succinoglycan with the structure shown below. (S)-pyruvic acid is found stoichiometrically as 4,6-O-ketal substituent of terminal glucose. Succinic acid is present in 40% of the repeating units and it is attached to O-6 of the 3-linked glucose next to the pyruvate carrying sugar. Some evidence is found that a small amount of succinic acid (ca. 6% of the total) is linked to O-6 of another undetermined glucose. [structure: see text]
13C NMR, 1H NMR, methylation, NMR-2D, partial acid hydrolysis, GC-MS, sugar analysis, MS/MS, enzymatic degradation, paper chromatography, HPLC, GPC
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,4,4,6,6,3,3,6 xSPyr 175.46 101.91 25.84
3,4,4,6,6,3,3 bDGlcp 104.63 75.67 74.00 77.32 66.98 65.72
3,4,4,6,6,3,6 xXSuc 178.12 30.24 30.09 175.83
3,4,4,6,6,3 bDGlcp 104.07 74.47 85.06 69.08 74.53 64.59
3,4,4,6,6 bDGlcp 104.01 74.20 86.51 69.43 76.99 61.98
3,4,4,6 bDGlcp 104.25 74.35-74.41 76.84 70.70 76.07-76.18 70.02
3,4,4 bDGlcp 104.03 74.35-74.41 76.84 70.94 76.23 70.40
3,4 bDGlcp 103.63 74.26 75.53 80.27 76.07-76-18 61.26
3 bDGlcp 104.92 74.35-74.41 75.36 79.62 75.90 61.10
bDGalp 97.47 72.16 83.98 69.70 76.09 62.23
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,4,4,6,6,3,3,6 xSPyr - - 1.518
3,4,4,6,6,3,3 bDGlcp 4.831 3.406 3.699 3.454 3.505 3.691-4.095
3,4,4,6,6,3,6 xXSuc - 2.717 2.717 -
3,4,4,6,6,3 bDGlcp 4.726 3.554 3.737 3.556 3.683 4.289-4.516
3,4,4,6,6 bDGlcp 4.539 3.517 3.721 3.508 3.481 3.748-3.924
3,4,4,6 bDGlcp 4.552 3.327 3.516 3.479 3.625 3.868-4.217
3,4,4 bDGlcp 4.509 3.325 3.514 3.455 3.676 3.856-4.222
3,4 bDGlcp 4.541 3.367 3.650 3.680 3.623 3.824-3.978
3 bDGlcp 4.692 3.425 3.658 3.687 3.591 3.834-3.945
bDGalp 4.630 3.641 3.798 4.191 3.718 3.729-3.757
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,4,4,6,6,3,3,6 xSPyr 25.84/1.518
3,4,4,6,6,3,3 bDGlcp 104.63/4.831 75.67/3.406 74.00/3.699 77.32/3.454 66.98/3.505 65.72/3.691-4.095
3,4,4,6,6,3,6 xXSuc 30.24/2.717 30.09/2.717
3,4,4,6,6,3 bDGlcp 104.07/4.726 74.47/3.554 85.06/3.737 69.08/3.556 74.53/3.683 64.59/4.289-4.516
3,4,4,6,6 bDGlcp 104.01/4.539 74.20/3.517 86.51/3.721 69.43/3.508 76.99/3.481 61.98/3.748-3.924
3,4,4,6 bDGlcp 104.25/4.552 74.35-74.41/3.327 76.84/3.516 70.70/3.479 76.07-76.18/3.625 70.02/3.868-4.217
3,4,4 bDGlcp 104.03/4.509 74.35-74.41/3.325 76.84/3.514 70.94/3.455 76.23/3.676 70.40/3.856-4.222
3,4 bDGlcp 103.63/4.541 74.26/3.367 75.53/3.650 80.27/3.680 76.07-76-18/3.623 61.26/3.824-3.978
3 bDGlcp 104.92/4.692 74.35-74.41/3.425 75.36/3.658 79.62/3.687 75.90/3.591 61.10/3.834-3.945
bDGalp 97.47/4.630 72.16/3.641 83.98/3.798 69.70/4.191 76.09/3.718 62.23/3.729-3.757