NMR chemical shift prediction and structural elucidation of linker-containing oligo- and polysaccharides using the computer program CASPER

Dorst, Kevin M.; Widmalm, Göran

doi:10.1016/j.carres.2023.108937

Cited by 7 publications

(2 citation statements)

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“…4b), on the one hand, and from δ H1 5.06 at 98.3, 73.4, 73.0, 72.1, 70.3 and 61.4 ppm, on the other. Thus, the former spin-system identifies the glycerol residue as being linked to position 6 of the Glc side-chain residue and the latter as the non-substituted Glc side-chain, where the correlations in the latter spin-system are in agreement with the earlier analysis of SCC 7 as well as an NMR chemical shift prediction by CASPER 37 of the trisaccharide repeating unit of the WT SCC. Furthermore, the downfield NMR chemical shift displacement at C6 from 61.4 to 64.8 ppm is consistent with phosphorylation at this position 38 .…”

Section: Resultssupporting

confidence: 83%

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Structure and mechanism of biosynthesis ofStreptococcus mutanscell wall polysaccharide

Rush,

Zamakhaeva,

Murner

et al. 2024

Preprint

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Streptococcus mutans, the causative agent of human dental caries, expresses a cell wall attached Serotype c-specific Carbohydrate (SCC) that is critical for cell viability. SCC consists of a repeating →3)α-Rha(1→2)α-Rha(1→ polyrhamnose backbone, with glucose (Glc) side-chains and glycerol phosphate (GroP) decorations. This study reveals that SCC has one major and two minor Glc modifications. The major Glc modification, @[alpha]-Glc, attached to position 2 of 3-rhamnose, is installed by SccN and SccM glycosyltransferases and is the site of the GroP addition. The minor Glc modifications are @[beta]-Glc linked to position 4 of 3-rhamnose installed by SccP and SccQ glycosyltransferases, and @[alpha]-Glc attached to position 4 of 2- rhamnose installed by SccN working in tandem with an unknown enzyme. Both the major and the minor @[beta]-Glc modifications control bacterial morphology, but only the GroP and major Glc modifications are critical for biofilm formation.

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Section: Resultssupporting

confidence: 83%

“…4h, Table 3, double primed residues). The assignments of the NMR resonances from this trisaccharide RU are in excellent agreement with the 1 H and 13 C NMR chemical shifts predicted by the CASPER program 37 (Supplementary Fig. 6) substantiating the proposed structure (Fig.…”

Section: Resultssupporting

confidence: 79%