Stereoselective synthesis of optically active bicyclic -lactam carboxylic acids that target pilus biogenesis in pathogenic bacteria

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Fältnamn	Indikatorer	Metadata
000		02305naa a2200313 4500
001		oai:DiVA.org:umu-9967
003		SwePub
008		080603s2003 \| \|\|\|\|\|\|\|\|\|\|\|000 \|\|eng\|
024	7	a https://urn.kb.se/resolve?urn=urn:nbn:se:umu:diva-99672 URI
024	7	a https://doi.org/10.1039/b210551a2 DOI
040		a (SwePub)umu
041		a engb eng
042		9 SwePub
072	7	a ref2 swepub-contenttype
072	7	a art2 swepub-publicationtype
100	1	a Emtenäs, Hansu Umeå universitet,Kemiska institutionen4 aut
245	1 0	a Stereoselective synthesis of optically active bicyclic -lactam carboxylic acids that target pilus biogenesis in pathogenic bacteria
264		c 2003-03-11
264	1	b Royal Society of Chemistry (RSC),c 2003
338		a print2 rdacarrier
520		a 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.
700	1	a Carlsson, Marcusu Umeå universitet,Kemiska institutionen4 aut
700	1	a Pinkner, Jerome S4 aut
700	1	a Hultgren, Scott J4 aut
700	1	a Almqvist, Fredriku Umeå universitet,Kemiska institutionen4 aut0 (Swepub:umu)fral0001
710	2	a Umeå universitetb Kemiska institutionen4 org
773	0	t Organic & Biomolecular Chemistryd : Royal Society of Chemistry (RSC)g 1, s. 1308-14q 1<1308-14x 1477-0520x 1477-0539
856	4 8	u https://urn.kb.se/resolve?urn=urn:nbn:se:umu:diva-9967
856	4 8	u https://doi.org/10.1039/b210551a

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Av författaren/redakt...: Emtenäs, Hans; Carlsson, Marcus; Pinkner, Jerome ...; Hultgren, Scott ...; Almqvist, Fredri ...

Artiklar i publikationen: Organic & Biomol ...

Av lärosätet: Umeå universitet

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