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Metabolic Labeling of Pseudaminic Acid-Containing Glycans on Bacterial Surfaces
ACS Chemical Biology ( IF 3.5 ) Pub Date : 2018-09-19 00:00:00 , DOI: 10.1021/acschembio.8b00822 Gloria Andolina 1 , Ruohan Wei 1 , Han Liu 1 , Qing Zhang 1 , Xuemei Yang 2 , Huiluo Cao 3 , Sheng Chen 2 , Aixin Yan 3 , Xiang David Li 1 , Xuechen Li 1
ACS Chemical Biology ( IF 3.5 ) Pub Date : 2018-09-19 00:00:00 , DOI: 10.1021/acschembio.8b00822 Gloria Andolina 1 , Ruohan Wei 1 , Han Liu 1 , Qing Zhang 1 , Xuemei Yang 2 , Huiluo Cao 3 , Sheng Chen 2 , Aixin Yan 3 , Xiang David Li 1 , Xuechen Li 1
Affiliation
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The rise in antibiotic-resistant bacteria is causing worldwide concerns. The urgent need for new antibacterial drugs calls for new thinking and strategies to explore novel, narrow-spectrum, and pathogen-specific antibacterial targets. Legionaminic acid (Leg) and pseudaminic acid (Pse) are nonulosonic acid carbohydrates with structural similarity to eukaryotic sialic acid, and are distributed in numerous pathogenic Gram-negative bacteria as components of cell surface-associated glycans. They are involved in the host interaction, pathogenicity, antiphage defense mechanism, and immune escape mechanism. To further explore their biological significance, we developed a synthesis of 2-acetamido-4-azidoacetamido-2,4,6-trideoxy-l-altrose (Alt-4NAz) and 2-azidoacetamido-4-acetamido-2,4,6-trideoxy-l-altrose (Alt-2NAz), among which Alt-4NAz served as an effective chemical reporter to realize bacterial Pse metabolic labeling. The effectiveness of this chemical reporter has been demonstrated in Pseudomonas aeruginosa, Vibrio vulnificus, and Acinetobacter baumannii strains. Expectedly, this strategy can provide a useful assay to detect phenotypic presence of Pse biosynthesis and screen for agents targeting this pathway.
中文翻译：
细菌表面上含伪氨基酸的聚糖的代谢标记
抗生素抗性细菌的增加引起了全世界的关注。迫切需要新的抗菌药物，这需要新的思维和策略来探索新颖的，窄谱的和病原体特异性的抗菌靶标。军团胺酸（Leg）和伪氨酸（Pse）是与生物真核唾液酸具有结构相似性的壬二酸碳水化合物，并作为细胞表面相关聚糖的成分分布在许多致病性革兰氏阴性细菌中。它们参与宿主相互作用，致病性，抗噬菌体防御机制和免疫逃逸机制。为了进一步探索其生物学意义，我们开发了2-乙酰氨基-4- azidoacetamido -2,4,6-三脱氧的合成升-altrose（ALT-4NAz）和2- azidoacetamido -4-乙酰氨基-2,4,6- -三甲氧基-l-altrose（Alt-2NAz），其中Alt-4NAz可作为有效的化学报告基因来实现细菌Pse代谢标记。在铜绿假单胞菌，创伤弧菌和鲍曼不动杆菌菌株中已证明了该化学报告基因的有效性。预期地，该策略可以提供有用的测定法来检测Pse生物合成的表型存在，并筛选靶向该途径的药物。
更新日期：2018-09-19
中文翻译：
细菌表面上含伪氨基酸的聚糖的代谢标记
抗生素抗性细菌的增加引起了全世界的关注。迫切需要新的抗菌药物，这需要新的思维和策略来探索新颖的，窄谱的和病原体特异性的抗菌靶标。军团胺酸（Leg）和伪氨酸（Pse）是与生物真核唾液酸具有结构相似性的壬二酸碳水化合物，并作为细胞表面相关聚糖的成分分布在许多致病性革兰氏阴性细菌中。它们参与宿主相互作用，致病性，抗噬菌体防御机制和免疫逃逸机制。为了进一步探索其生物学意义，我们开发了2-乙酰氨基-4- azidoacetamido -2,4,6-三脱氧的合成升-altrose（ALT-4NAz）和2- azidoacetamido -4-乙酰氨基-2,4,6- -三甲氧基-l-altrose（Alt-2NAz），其中Alt-4NAz可作为有效的化学报告基因来实现细菌Pse代谢标记。在铜绿假单胞菌，创伤弧菌和鲍曼不动杆菌菌株中已证明了该化学报告基因的有效性。预期地，该策略可以提供有用的测定法来检测Pse生物合成的表型存在，并筛选靶向该途径的药物。
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