Revised structure of the capsular polysaccharide of Acinetobacter baumannii LUH5533 (serogroup O1) containing di-N-acetyllegionaminic acid

Shashkov, A. S.; Сенченкова, С. Н.; Popova, Anastasiya V.; Mei, Zhu; Shneider, Mikhail M.; Liu, Bin; Miroshnikov, Konstantin A.; Volozhantsev, Nikolay V.; Knirel, Yu. A.

doi:10.1007/s11172-015-1000-9

Cited by 21 publications

(6 citation statements)

References 22 publications

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“…[2, 4] Pathogenic bacterial LPSs containing Leg5,7Ac 2 and derivatives are attractive targets for developing bacterial polysaccharide vaccines and diagnostic tools (e.g. anti-carbohydrate antibodies).…”

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confidence: 99%

“…It is worth to note that Leg5,7Ac 2 α2–3Gal- and Leg5,7Ac 2 α2–6Gal-containing structures have been found in O-antigens [4b, 4c, 30] and an extracellular polysaccharide fraction, [4e] respectively, of various opportunistic pathogens. Therefore, the obtained thiotolyl β-glycosides (compounds 15 – 16 and 21 – 22 ) can be used to form building blocks for efficient chemical synthesis of more complex glycosides similar to those described before for Neu5Ac-containing sialosides.…”

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confidence: 99%

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A Diazido Mannose Analogue as a Chemoenzymatic Synthon for Synthesizing Di‐N‐acetyllegionaminic Acid‐Containing Glycosides

Santra

Xiao

et al. 2018

Angew Chem Int Ed

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A chemoenzymatic synthon was designed to expand the scope of the chemoenzymatic synthesis of carbohydrates. The synthon was enzymatically converted into carbohydrate analogues, which were readily derivatized chemically to produce the desired targets. The strategy is demonstrated for the synthesis of glycosides containing 7,9-di-N-acetyllegionaminic acid (Leg5,7Ac ), a bacterial nonulosonic acid (NulO) analogue of sialic acid. A versatile library of α2-3/6-linked Leg5,7Ac -glycosides was built by using chemically synthesized 2,4-diazido-2,4,6-trideoxymannose as a chemoenzymatic synthon for highly efficient one-pot multienzyme (OPME) sialylation followed by downstream chemical conversion of the azido groups into acetamido groups. The syntheses required 10 steps from commercially available d-fucose and had an overall yield of 34-52 %, thus representing a significant improvement over previous methods. Free Leg5,7Ac monosaccharide was also synthesized by a sialic acid aldolase-catalyzed reaction.

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confidence: 99%

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confidence: 99%

A Diazido Mannose Analogue as a Chemoenzymatic Synthon for Synthesizing Di‐N‐acetyllegionaminic Acid‐Containing Glycosides

Santra

Xiao

et al. 2018

Angew Chem Int Ed

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“…The potential atr gene(s) should be present in the genomes of NIPH 329 and SDF but absent in strains with related but unacetylated CPS structures, such as K7 and K90 CPS produced respectively by A . baumannii isolates LUH5533 [27] and LUH5553 [28].…”

Section: Resultsmentioning

confidence: 99%

“…Related CPS structures of A . baumannii LUH5553 [28] and LUH5533 [27] without 4-O-acetylation of the non-2-ulosonic acid residue. Glycosyltransferases, polymerases and acetyltrasferases are indicated in bold next the linkage they are assigned to.…”

Section: Resultsmentioning

confidence: 99%

“…Formation of all these linkages catalyzed by the glycosyltransferases encoded by the KL46 gene cluster could be assigned due to the close relationship to those encoded in the KL5 gene cluster. Their roles were previously assigned via comparison of the K5 [5] and K7 [27] CPS structures produced by isolates carrying the KL5 and KL7 gene clusters, a closely related pair that differ only in a segment that includes the wzy gene [2]. KL46 and KL5 are also a closely related pair of gene clusters that differ only in a central segment that includes the genes for synthesis of the non-2-ulosonic acid side-branch (Fig 1).…”

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confidence: 99%

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The K46 and K5 capsular polysaccharides produced by Acinetobacter baumannii NIPH 329 and SDF have related structures and the side-chain non-ulosonic acids are 4-O-acetylated by phage-encoded O-acetyltransferases

et al. 2019

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Acinetobacter baumannii isolate NIPH 329 carries a novel capsular polysaccharide (CPS) gene cluster, designated KL46, that is closely related to the KL5 locus in A . baumannii isolate SDF but includes genes for synthesis of 5,7-diacetamido-3,5,7,9-tetradeoxy- l - glycero - l - manno -non-2-ulosonic (di- N -acetylpseudaminic) acid (Pse5Ac7Ac) instead of the corresponding D - glycero - D - galacto isomer (di- N -acetyllegionaminic acid) (Leg5Ac7Ac). In agreement with the genetic content of KL46, chemical studies of the K46 CPS produced by NIPH 329 revealed a branched tetrasaccharide repeat (K unit) with an overall structure the same as K5 from SDF but with â-Pse5Ac7Ac replacing α-Leg5Ac7Ac. As for K5, the K46 unit begins with d -Gal p NAc and includes α- d -Glc p NAc-(1→3)- d -Gal p NAc and α- d -Gal p -(1→6)- d -Glc p NAc linkages, formed by Gtr14 and Gtr15 glycosyltransferases, respectively. The Gtr94 K46 glycosyltransferase, which is related to Gtr13 K5, links Pse5Ac7Ac to d -Gal p in the growing K unit via a â-(2→6) linkage. Nearly identical Wzy enzymes connect the K46 and K5 units via a α-D-Gal p NAc-(1→3)-α-D-Gal p linkage to form closely related CPSs. Both Pse5Ac7Ac in K46 and Leg5Ac7Ac in K5 are acetylated at O4 but no acetyltransferase gene is present in KL46 or KL5. Related acetyltransferases were found encoded in the NIPH 329 and SDF genomes, but not in other strains carrying an unacetylated Pse or Leg derivative in the CPS. The genes encoding the acetyltransferases were in different putative phage genomes. However, related acetyltransferases were rare among the >3000 publically available genome sequences.

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A Diazido Mannose Analogue as a Chemoenzymatic Synthon for Synthesizing Di‐N‐acetyllegionaminic Acid‐Containing Glycosides

Santra

Xiao

et al. 2018

Angewandte Chemie

View full text Add to dashboard Cite

A chemoenzymatic synthon was designed to expand the scope of the chemoenzymatic synthesis of carbohydrates. The synthon was enzymatically converted into carbohydrate analogues, which were readily derivatized chemically to produce the desired targets. The strategy is demonstrated for the synthesis of glycosides containing 7,9‐di‐N‐acetyllegionaminic acid (Leg5,7Ac2), a bacterial nonulosonic acid (NulO) analogue of sialic acid. A versatile library of α2‐3/6‐linked Leg5,7Ac2‐glycosides was built by using chemically synthesized 2,4‐diazido‐2,4,6‐trideoxymannose as a chemoenzymatic synthon for highly efficient one‐pot multienzyme (OPME) sialylation followed by downstream chemical conversion of the azido groups into acetamido groups. The syntheses required 10 steps from commercially available d‐fucose and had an overall yield of 34–52 %, thus representing a significant improvement over previous methods. Free Leg5,7Ac2 monosaccharide was also synthesized by a sialic acid aldolase‐catalyzed reaction.

show abstract

Revised structure of the capsular polysaccharide of Acinetobacter baumannii LUH5533 (serogroup O1) containing di-N-acetyllegionaminic acid

Cited by 21 publications

References 22 publications

A Diazido Mannose Analogue as a Chemoenzymatic Synthon for Synthesizing Di‐N‐acetyllegionaminic Acid‐Containing Glycosides

A Diazido Mannose Analogue as a Chemoenzymatic Synthon for Synthesizing Di‐N‐acetyllegionaminic Acid‐Containing Glycosides

The K46 and K5 capsular polysaccharides produced by Acinetobacter baumannii NIPH 329 and SDF have related structures and the side-chain non-ulosonic acids are 4-O-acetylated by phage-encoded O-acetyltransferases

A Diazido Mannose Analogue as a Chemoenzymatic Synthon for Synthesizing Di‐N‐acetyllegionaminic Acid‐Containing Glycosides

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