Structure and genetics of the O-antigen of Enterobacter cloacae C6285 containing di-N-acetyllegionaminic acid

Filatov, Andrei V.; Wang, Min; Wang, Wenjing; Perepelov, Andrei V.; Shashkov, Alexander S.; Wang, Lei; Knirel, Yuriy A.

doi:10.1016/j.carres.2014.01.012

Cited by 15 publications

(9 citation statements)

References 21 publications

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“…Leg5,7Ac 2 α2‐3Gal‐ and Leg5,7Ac 2 α2‐6Gal‐containing structures have been found in O‐antigens– and an extracellular polysaccharide fraction, 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 the efficient chemical synthesis of more complex glycosides similar to those described before for Neu5Ac‐containing sialosides…”

Section: Figurementioning

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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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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Section: Figurementioning

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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“…1–3 It is the major component of the lipopolysaccharide virulence factor of Legionella pneumophila , where it occurs in the form of the α-(2→4)-linked (equatorial) homopolymer 2 . 4–7 Additionally, legionaminic acid glycosides are also found in the lipopolysaccharides of numerous other important Gram-negative pathogens 1–2 including, for example, Campylobacter jejuni , 8–10 Cronobacter turicensis , 11 Enterobacter cloacae , 12 and Acinetobacter baumannii . 13 C Consequently, legionamic acid glycosides are candidates for antibacterial vaccine development and for use in diagnostic tools.…”

Section: Introductionmentioning

confidence: 99%

“…Legionaminic acid ( 1 ) is a member of the sialic acid family of nine carbon amino deoxy ulosonic acids that is only found in bacteria. − It is the major component of the lipopolysaccharide virulence factor of Legionella pneumophila , where it occurs in the form of the α-(2→4)-linked (equatorial) homopolymer 2 . − Additionally, legionaminic acid glycosides are also found in the lipopolysaccharides of numerous other important Gram-negative pathogens, , including, for example, Campylobacter jejuni , − Cronobacter turicensis , Enterobacter cloacae , and Acinetobacter baumannii . Consequently, legionamic acid glycosides are candidates for antibacterial vaccine development and for use in diagnostic tools. , To facilitate such studies, broader availability of legionaminic acid and its glycosides is required, and while recent biosynthetic work is promising in terms of accessing legionaminic acid , itself and its glycosides, , practical chemical syntheses are required.…”

Section: Introductionmentioning

confidence: 99%

Stereoselective Synthesis of the Equatorial Glycosides of Legionaminic Acid

2017

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The synthesis of a legionaminic acid donor from N-acetyl neuraminic acid in fifteen steps and 17% overall yield is described. Activation of the adamantanyl thioglycoside in the donor with N-iodosuccinimide and trifluoromethanesulfonic acid in dichloromethane and acetonitrile at −78 °C in the presence of primary, secondary and tertiary alcohols affords the corresponding glycosides in excellent yield and good to excellent equatorial selectivity. In particular coupling to the 4-OH of a suitably protected neuraminic acid derivative affords a disaccharide that closely resembles the glycosidic linkage in the polylegionaminic acid from the lipopolysaccharide of the Legionella pneumophila virulence factor. A straightforward deprotection sequence enables conversion of the protected glycosides to the free N,N-diacetyl legionaminic acid glycosides.

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“…The presence of legionaminic acids 2 and 3 (LegA) within glycoconjugates of bacterial pathogens , makes them ideal targets for pathogen detection and for the development of vaccines. Interestingly, legionaminic acid is also found in other prominent human pathogens such as Acinetobacter baumannii, Enterobacter cloacae, and Campylobacter jejuni. , …”

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confidence: 99%

Total Synthesis of Legionaminic Acid as Basis for Serological Studies

2015

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Legionaminic acid is a nine-carbon diamino monosaccharide that is found coating the surface of various bacterial human pathogens. Its unique structure makes it a valuable biological probe, but access via isolation is difficult and no practical synthesis has been reported. We describe a stereoselective synthesis that yields a legionaminic acid building block as well as linker-equipped conjugation-ready legionaminic acid starting from cheap d-threonine. To set the desired amino and hydroxyl group pattern of the target, we designed a concise sequence of stereoselective reactions. The key transformations rely on chelation-controlled organometallic additions and a Petasis multicomponent reaction. The legionaminic acid was synthesized in a form that enables attachment to surfaces. Glycan microarray containing legionaminic acid revealed that human antibodies bind the synthetic glycoside. The synthetic bacterial monosaccharide is a valuable probe to detect an immune response to bacterial pathogens such as Legionella pneumophila, the causative agent of Legionnaire's disease.

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Structure and genetics of the O-antigen of Enterobacter cloacae C6285 containing di-N-acetyllegionaminic acid

Cited by 15 publications

References 21 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

Stereoselective Synthesis of the Equatorial Glycosides of Legionaminic Acid

Total Synthesis of Legionaminic Acid as Basis for Serological Studies

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