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Synthesis of pure stereoisomers of benzo[b]thienyl dehydrophenylalanines by Suzuki cross-coupling. Preliminary studies of antimicrobial activity

2004Journal article Open access
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dc.contributor.authorAbreu, Ana S.
dc.contributor.authorFerreira, Paula M.T.
dc.contributor.authorMonteiro, Luís S.
dc.contributor.authorFerreira, Isabel C.F.R.
dc.contributor.authorCalhelha, Ricardo C.
dc.contributor.authorEstevinho, Leticia M.
dc.date.accessioned2008-09-12T14:19:39Z
dc.date.available2008-09-12T14:19:39Z
dc.date.issued2004
dc.description.abstractSeveral benzo[b]thienyldehydrophenylalanines were synthesized from pure stereoisomers of the methyl ester of N-(tertbutoxycarbonyl)- b-bromodehydrophenylalanine as an extension of our previously reported method for the synthesis of dehydrotryptophan analogues to dehydrophenylalanine derivatives. The latter were obtained in high yields by N-deprotection and bromination of N,N-bis-(tertbutoxycarbonyl)-( Z)-dehydrophenylalanine using TFA and NBS. This was carried out in two steps or in a one pot procedure resulting in different E/Z ratios. These compounds were coupled under Suzuki cross-coupling conditions [Pd(PPh3)4, Na2CO3, DME/H2O] with several boronic benzo[b]thienyl acids in good to high yields maintaining the stereochemistry of the starting materials. The best yields were obtained when the boronic acid was in position 7 of the benzo[b]thiophene and with the E isomer of the brominated dehydrophenylalanine. In some cases it was possible to increase the lower yields by changing the Pd source to PdCl2(PPh3)2. A model dipeptide was prepared coupling a benzo[b]thienyldehydrophenylalanine with the methyl ester of alanine. Preliminary antimicrobial studies were performed with both isomers of one of the b, b-diaryldehydroalanines obtained. The results show that the compounds are selective and very active (very low MICs) against Gram positive bacteria (B. cereus and B. subtilis) the Z-isomer being more active. The compounds are also active against Candida albicans presenting similar MICs.en
dc.identifier.citationAbreu, Ana S.; Ferreira, Paula M.T.; Monteiro, Luís S.; Ferreira, Isabel C.F.R.; Calhelha, Ricardo C.; Estevinho, Leticia M. (2004). Synthesis of pure stereoisomers of benzo[b]thienyl dehydrophenylalanines by Suzuki cross-coupling. Preliminary studies of antimicrobial activity. Tetrahedron. ISSN 0040-4020. 60:54, p. 11821-11828en
dc.identifier.doi10.1016/j.tet.2004.09.107
dc.identifier.issn0040-4020
dc.identifier.urihttp://hdl.handle.net/10198/822
dc.language.isoengen
dc.publisherElsevieren
dc.relationSynthesis of non-proteinogenic amino acids with biological and/or photochromic activities
dc.relationSÍNTESE DE NOVOS FOTOBIOSSENSORES DERIVADOS DE AMINOÁCIDOS BENZO b TIOFÉNICOS
dc.subjectAmino acidsen
dc.subjectDehydrophenylalaninesen
dc.subjectBenzo[b]thiophenesen
dc.subjectSuzuki couplingen
dc.subjectPalladiumen
dc.subjectAntimicrobialen
dc.titleSynthesis of pure stereoisomers of benzo[b]thienyl dehydrophenylalanines by Suzuki cross-coupling. Preliminary studies of antimicrobial activityen
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitleSynthesis of non-proteinogenic amino acids with biological and/or photochromic activities
oaire.awardTitleSÍNTESE DE NOVOS FOTOBIOSSENSORES DERIVADOS DE AMINOÁCIDOS BENZO b TIOFÉNICOS
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/POCI/POCTI%2FQUI%2F32689%2F2000/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT//SFRH%2FBD%2F4709%2F2001/PT
oaire.fundingStreamPOCI
person.familyNameFerreira
person.familyNameCalhelha
person.familyNameEstevinho
person.givenNameIsabel C.F.R.
person.givenNameRicardo C.
person.givenNameLetícia M.
person.identifier144781
person.identifier.ciencia-id9418-CF95-9919
person.identifier.ciencia-idF313-E3CE-554E
person.identifier.ciencia-idBA14-09D6-A406
person.identifier.orcid0000-0003-4910-4882
person.identifier.orcid0000-0002-6801-4578
person.identifier.orcid0000-0002-9249-1948
person.identifier.ridE-8500-2013
person.identifier.ridJ-2172-2014
person.identifier.scopus-author-id36868826600
person.identifier.scopus-author-id6507978333
person.identifier.scopus-author-id6506577664
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
rcaap.rightsopenAccess
rcaap.typearticleen
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