Proton magnetic resonance spectra of D-gluco-oligosaccharides and D-glucans

Usui, Taichi; Yokoyama, Minoru; Yamaoka, Naotaka; Matsuda, Kazuo; Tuzimura, Katura; Sugiyama, Horoshi; Seto, Shûichi

doi:10.1016/s0008-6215(00)82944-4

Cited by 87 publications

(18 citation statements)

References 35 publications

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“…The results of 13C-and 1H-NMR spectroscopy confirmed the structural similarity of the synthase product and curdlan. The positions of 13C ( Figure 4) and ~H (data not shown) resonance signals are essentially the same for both polysaccharides and correspond with those previously reported for curdlan (Harada, 1979;Saito et aL, 1977aSaito et aL, , 1981 and other (l~3)-~-glucosyl oligomers or polymers (Bock et aL, 1984;Saito et aL, 1977bSaito et aL, , 1979Usui et aL, 1974). The 13C resonance signals at 60.9, 68.5, 72.9, 76.4, 86.2 and 103.1 p.p.m, in the 13C-NMR spectra ( Figure 4) are assignable to carbons -6, -4,-2, -5, -3 and -1, respectively (Bock et aL, 1984;Harada, 1979;Saito et aL, 1977aSaito et aL, , 1977bSaito et aL, , 1979Saito et aL, , 1981.…”

Section: Nmr Spectroscopysupporting

confidence: 88%

In vitro synthesis of a microfibrillar (1→3)‐β‐glucan by a ryegrass (Lolium multiflorum) endosperm (1→3)‐β‐glucan synthase enriched by product entrapment

1995

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Section: Nmr Spectroscopysupporting

confidence: 88%

In vitro synthesis of a microfibrillar (1→3)‐β‐glucan by a ryegrass (Lolium multiflorum) endosperm (1→3)‐β‐glucan synthase enriched by product entrapment

1995

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“…The presence of α-1,4 links in the oligosaccharide products from maltotetraose extension was shown by NMR spectroscopy (Fig. 2d), with no evidence for other α-1, n or β-1, n links 12 . Together, these observations showed that the enzyme exhibits an α-retaining catalytic mechanism.…”

Section: Resultsmentioning

confidence: 84%

Self-poisoning of Mycobacterium tuberculosis by targeting GlgE in an α-glucan pathway

et al. 2010

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New chemotherapeutics are urgently required to control the tuberculosis pandemic. We describe a new pathway from trehalose to α-glucan in Mycobacterium tuberculosis comprising four enzymatic steps mediated by TreS, Pep2, GlgE (which has been identified as a maltosyltransferase that uses maltose 1-phosphate) and GlgB. Using traditional and chemical reverse genetics, we show that GlgE inactivation causes rapid death of M. tuberculosis in vitro and in mice through a self-poisoning accumulation of maltose 1-phosphate. Poisoning elicits pleiotropic phosphosugar-induced stress responses promoted by a self-amplifying feedback loop where trehalose-forming enzymes are upregulated. Moreover, the pathway from trehalose to α-glucan exhibited a synthetic lethal interaction with the glucosyltransferase Rv3032, which is involved in biosynthesis of polymethylated α-glucans, because key enzymes in each pathway could not be simultaneously inactivated. The unique combination of maltose 1-phosphate toxicity and gene essentiality within a synthetic lethal pathway validates GlgE as a distinct potential drug target that exploits new synergistic mechanisms to induce death in M. tuberculosis.

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“…Most characteristic is the resonance at 5.20p.p.m. (J1-J2 = 3.3 Hz) as a result of the a-anomeric protons (Usui et al, 1974). As in a,a-trehalose the two glucose residues are identical, only one doublet being observed.…”

Section: 4mentioning

confidence: 77%

Osmotically induced oligo- and polysaccharide synthesis by Rhizobium meliloti SU-47

Breedveld¹,

Zevenhuizen²,

Zehnder³

1990

Journal of General Microbiology

106

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In standard liquid medium containing 5 g mamitoll-' and 1 g glutamic acid 1-l, Rhizobium mefifoti SU-47 cells accumulated 350 mg cyclic 1,2-Q-glucans (g protein)-'. The cyclic glucans were 36 % glycerol-1-phosphatesubstituted and 64% were uncharged. In the same medium with 10 g mamitoll-' , repeating units of succinoglycan (1110 mg 1-l) were found as extracellular carbohydrates, and only low amounts of the succinoglycan polymer (up to 300 mg 1-l) were excreted. By raising the osmotic pressure of the medium by the addition of NaCl or other ionic and non-ionic osmolytes, succinoglycan production could be stimulated: up to 2.4 g 1-1 at 0.2 M-NaCI was produced at the expense of the repeating units. Above 0.2 M-NaCl growth was slowed down, and succinoglycan excretion diminished. At 1 M-NaCl growth stopped completely. In standard medium containing 0.6 M-NaCl the amount of cellular cyclic l,2-Q-glucans was lowered to 150 mg (g protein)-l out of which the glycerol-1-phosphatesubstituted glucan fraction was reduced to 15%. Instead, high amounts of oligosaccharides were synthesized as osmoprotectants, with trehalose as the major component [up to 200 mg (g protein)-']. Glycogen synthesis was completely suppressed at this salt concentration, while p l y Q-hydroxybutyric acid synthesis was unaffected.

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Proton magnetic resonance spectra of D-gluco-oligosaccharides and D-glucans

Cited by 87 publications

References 35 publications

In vitro synthesis of a microfibrillar (1→3)‐β‐glucan by a ryegrass (Lolium multiflorum) endosperm (1→3)‐β‐glucan synthase enriched by product entrapment

In vitro synthesis of a microfibrillar (1→3)‐β‐glucan by a ryegrass (Lolium multiflorum) endosperm (1→3)‐β‐glucan synthase enriched by product entrapment

Self-poisoning of Mycobacterium tuberculosis by targeting GlgE in an α-glucan pathway

Osmotically induced oligo- and polysaccharide synthesis by Rhizobium meliloti SU-47

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