Study of a novel glycoconjugate, thiopeptidoglycan, and a novel polysaccharide lyase, thiopeptidoglycan lyase

Kondo, Kengo; Takeda, Minoru; Ejima, Wataru; Kawasaki, Yuta; Umezu, Takuto; Yamada, Mikio; Koizumi, Jun–ichi; Mashima, Tsukasa; Katahira, Masato

doi:10.1016/j.ijbiomac.2010.11.009

Cited by 16 publications

(23 citation statements)

References 18 publications

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“…Sphaerotilus natans and Leptothrix cholodnii are typical sheath formers of β-Proteobacteria [4] and their SFPs are polymeric glycoconjugates of similar structure [24,25]. The SFPs were collectively named thiopeptidoglycan because of their resemblance to peptidoglycan [24]. Thiopeptidoglycan is an amphoteric glycan that has a pentasaccharide repeating unit modified with a thiolic dipeptide composed of glycine and cysteine.…”

Section: Discussionmentioning

confidence: 99%

Presence of N-l-lactyl-d-perosamine residue in the sheath-forming polysaccharide of Thiothrix fructosivorans

Kawasaki

Kondo

Narizuka

et al. 2016

International Journal of Biological Macromolecules

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Thiothrix fructosivorans forms a microtube (sheath) that encloses a line of cells. This sheath is an assemblage of [→4)-GlcN-(1→4)-Glc-(1→]n with side chains of Rha4N-(1→3)-Fuc(1→ at position 3 of Glc. The sheath-forming polysaccharide (SFP) may have some substitutions but this is not yet confirmed. To investigate the possible substitutions, the sheath was prepared by mild treatments. Solid-state NMR analysis suggested the presence of N-substitution. The sheath was hydrolyzed with concentrated HCl at 0°C, followed by derivatization with 4-aminobenzoic acid ethyl ester (ABEE). The presence of N-lactyl-Rha4N-Fuc-ABEE was suggested by NMR spectroscopy. Lactic acid was determined to be the l-isomer by chiral HPLC analysis. To estimate the N-lactylation degree, the sheath was N-acetylated. N-Acetyl-Rha4N-Fuc-ABEE and N-lactyl-Rha4N-Fuc-ABEE were then collectively recovered, and their abundance ratio was determined to be 1:4 by NMR analysis. When hydrolysis was performed at 40°C, GlcNAc-ABEE was obtained. For estimation of the N-acetylation degree, the sheath was N-acetylated with deuterated acetic anhydride and then N-acetyl-GlcN-ABEE was prepared. The content of deuterated N-acetyl-GlcN-ABEE was determined to be 50% based on the relative intensity of the acetyl proton signal in the 1D-(1)H NMR spectrum. It was concluded that Rha4N is mostly N-l-lactylated and GlcN is substoichiometrically N-acetylated.

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Section: Discussionmentioning

confidence: 99%

Presence of N-l-lactyl-d-perosamine residue in the sheath-forming polysaccharide of Thiothrix fructosivorans

Kawasaki

Kondo

Narizuka

et al. 2016

International Journal of Biological Macromolecules

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“…The Sphaerotilus-Leptothrix sheaths are formed from thiopeptidoglycan molecules, which have a backbone with amphoteric glycan and are grafted with a cysteine-rich dipeptide. NaOH or hydrazine treatment brings about removal of the peptide moieties of thiopeptidoglycan molecules and leads to irreversible collapse of the sheath (microtube) structure [15]. Resistance of the Thiothrix sheath to peptide bond-cleaving reagents indicates that unlike Sphaerotilus-Leptothrix sheath, Thiothrix sheath does not depend on the peptide moiety to maintain the microtubular structure.…”

Section: Discussionmentioning

confidence: 99%

“…Further, the sugar composition of the Thiothrix sheath is different from that of the Sphaerotilus-Leptothrix sheath. The Thiothrix type of sheathforming polymer mainly consists of alternating glucosaminoglucan and lacks uronic acid, while the Sphaerotilus-Leptothrix type of polymer has an amphoteric glycan core that contains uronic acid [15]. Incorporation of deoxypentose, though it remains unidentified, is another distinctive feature of the Thiothrix sheath because the Sphaerotilus-Leptothrix sheaths do not contain this type of monosaccharide.…”

Section: Discussionmentioning

confidence: 99%

“…This contributes to the uniqueness and functionality of sheathforming polymers. In recent years, marked progress was made in characterizing the sheath-forming polymers of ␤-Proteobacteria, namely, the genera Sphaerotilus and Leptothrix [14,15]. Members of these genera are widely distributed heterotrophic iron oxidizers and comprise the Sphaerotilus-Leptothrix group of bacteria as a basis of their taxonomical relatedness [10,16,17].…”

Section: Introductionmentioning

confidence: 99%

“…Members of these genera are widely distributed heterotrophic iron oxidizers and comprise the Sphaerotilus-Leptothrix group of bacteria as a basis of their taxonomical relatedness [10,16,17]. Because their sheath-forming polymers have similar chemical structures, they are collectively named thiopeptidoglycan, which is a subcategory of peptidoglycans [15]. Thiopeptidoglycan is a peculiar glycoconjugate that has a straight-chained amphoteric heteropolysaccharide core grafted with a dipeptide composed of glycine and l-cysteine.…”

Section: Introductionmentioning

confidence: 99%

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Presence of alternating glucosaminoglucan in the sheath of Thiothrix nivea

Takeda

Kondo

Yamada

et al. 2012

International Journal of Biological Macromolecules

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Patterns of sheath elongation, cell proliferation, and manganese(II) oxidation in Leptothrix cholodnii

et al. 2012

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Leptothrix cholodnii is a Mn(II)-oxidizing and sheath-forming member of the class β-Proteobacteria. Its sheath is a microtube-like filament that contains a chain of cells. From a chemical perspective, the sheath can be described as a supermolecule composed of a cysteine-rich polymeric glycoconjugate, called thiopeptidoglycan. However, the mechanism that controls the increase in sheath length is unknown. In this study, we attempted to detect sheath elongation through microscopic examination by using conventional reagents. Selective fluorescent labeling of preexisting or newly formed regions of the sheath was accomplished using combinations of biotin-conjugated maleimide, propionate-conjugated maleimide, and a fluorescent antibiotin antibody. Epifluorescence microscopy indicated that the sheath elongates at the terminal regions. On the bases of this observation, we assumed that the newly secreted thiopeptidoglycan molecules are integrated into the preexisting sheath at its terminal ends. Successive phase-contrast microscopy revealed that all cells proliferate at nearly the same rate regardless of their positions within the sheath. Mn(II) oxidation in microcultures was also examined with respect to cultivation time. Results suggested that the deposition of Mn oxides is notable in the aged regions. The combined data reveal the spatiotemporal relationships among sheath elongation, cell proliferation, and Mn oxide deposition in L. cholodnii.

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Study of a novel glycoconjugate, thiopeptidoglycan, and a novel polysaccharide lyase, thiopeptidoglycan lyase

Cited by 16 publications

References 18 publications

Presence of N-l-lactyl-d-perosamine residue in the sheath-forming polysaccharide of Thiothrix fructosivorans

Presence of N-l-lactyl-d-perosamine residue in the sheath-forming polysaccharide of Thiothrix fructosivorans

Presence of alternating glucosaminoglucan in the sheath of Thiothrix nivea

Patterns of sheath elongation, cell proliferation, and manganese(II) oxidation in Leptothrix cholodnii

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