Search: onr:"swepub:oai:DiVA.org:umu-9967" >
Stereoselective syn...
Stereoselective synthesis of optically active bicyclic -lactam carboxylic acids that target pilus biogenesis in pathogenic bacteria
-
- Emtenäs, Hans (author)
- Umeå universitet,Kemiska institutionen
-
- Carlsson, Marcus (author)
- Umeå universitet,Kemiska institutionen
-
Pinkner, Jerome S (author)
-
show more...
-
Hultgren, Scott J (author)
-
- Almqvist, Fredrik (author)
- Umeå universitet,Kemiska institutionen
-
show less...
-
(creator_code:org_t)
- 2003-03-11
- 2003
- English.
-
In: Organic & Biomolecular Chemistry. - : Royal Society of Chemistry (RSC). - 1477-0520 .- 1477-0539. ; 1, s. 1308-14
- Related links:
-
https://urn.kb.se/re...
-
show more...
-
https://doi.org/10.1...
-
show less...
Abstract
Subject headings
Close
- Optically active bicyclic -lactams were synthesized, starting from 2-H-2-thiazolines and Meldrum's acid derivatives. Several methods to accomplish an ester hydrolysis without damaging the -lactam framework were investigated. A rapid CsOH saponification of the -lactam methyl esters was developed and protonation of the Cs-carboxylates by Amberlite (IR-120 H+) afforded a series of bicyclic -lactam carboxylic acids. Moreover, a convenient method for the synthesis of 2-H-2-thiazolinecarboxylic acid methyl ester 2 was developed. Bicyclic -lactam carboxylic acids 7a–g and aldehydes 4a–d were screened for their affinity to the bacterial periplasmic chaperone PapD using a surface plasmon resonance technique. -Lactams substituted with large acyl substituents showed better binding to the chaperone than the native C-terminal peptide PapG 8, demonstrating that bicyclic -lactams constitute a new class of potential bacterial chaperone inhibitors.
Publication and Content Type
- ref (subject category)
- art (subject category)
Find in a library
To the university's database