| Title: |
Total synthesis of legionaminic acid as basis for serological studies |
| Authors: |
Matthies, S.; Stallforth, P.; Seeberger, P. |
| Source: |
Journal of the American Chemical Society |
| Publication Year: |
2015 |
| Collection: |
Max Planck Society: MPG.PuRe |
| Description: |
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. |
| Document Type: |
article in journal/newspaper |
| File Description: |
application/pdf |
| Language: |
unknown |
| Availability: |
http://hdl.handle.net/11858/00-001M-0000-0026-B82F-5; http://hdl.handle.net/11858/00-001M-0000-0026-B831-E; http://hdl.handle.net/11858/00-001M-0000-0026-B832-C; http://hdl.handle.net/11858/00-001M-0000-0026-B833-A |
| Accession Number: |
edsbas.65421C5B |
| Database: |
BASE |