Laccase-induced derivatization of unprotected amino acid L-tryptophan by coupling with p-hydroquinone 2,5-dihydroxy-N-(2-hydroxyethyl)-benzamide

Manda, Katrin; Hammer, Elke; Mikolasch, Annett; Gördes, Dirk; Thurow, Kerstin; Schauer, Frieder

doi:10.1007/s00726-005-0276-8

Cited by 36 publications

(19 citation statements)

References 51 publications

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“…Signals for phenolic hydroxy groups could not be detected, but signals for three amine protons were observed. All results together confirm the oxidation of the p-hydroquinone to a quinone as described previously for hybrid dimer formation from 2,5-dihydroxybenzoic acid derivatives with penicillins, 1) amino acids, 21) and primary aromatic amines, 2,3) and for the hybrid dimer formation from 3,4-dichloraniline with protocatechuic acid and syringic acid. 22,23) Biological Activity of the Biotransformation Products All products (3a to 3p) showed a moderate to strong growth inhibition of several Gram positive strains, among them multidrug resistant Staphylococcus and Enterococcus strains, and of the Gram negative strain E. coli in the agar diffusion assay (Table 1, data for 3a to 3d, all other data in supporting information available via e-mail: annett.mikolasch@gmx.de), but not against Pseudomonas aeruginosa and P. maltophilia.…”

Section: Resultssupporting

confidence: 89%

“…Comparable straight forward biotransformation of educts to products we found also for hybrid dimer formation from 2,5-dihydroxybenzoic acid derivatives with aminopenicillins, 1) amino acids, 21) and primary aromatic amines, 2,3) and from 3-(3,4-dihydroxy-phenyl)-propionic acid with 1-hexylamine. 4) Different reaction kinetics were described for hybrid dimer formation from 3,4-dichloroaniline and syringic acid 22) or 3-(3,4-dihydroxy-phenyl)propionic acid and 4-aminobenzoic acid.…”

Section: Resultssupporting

confidence: 64%

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Novel Cephalosporins Synthesized by Amination of 2,5-Dihydroxybenzoic Acid Derivatives Using Fungal Laccases II

Mikolasch

Niedermeyer

Lalk

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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Sixteen novel cephalosporins were synthesized by amination of 2,5-dihydroxybenzoic acid derivatives with the aminocephalosporins cefadroxil, cefalexin, cefaclor, and the structurally related carbacephem loracarbef using laccases from Trametes sp. or Myceliophthora thermophila. All products inhibited the growth of several Gram positive bacterial strains in the agar diffusion assay, among them methicillin-resistant Staphylococcus aureus and vancomycin-resistant enterococci. The products protected mice against an infection with Staphylococcus aureus lethal to the control animals. Cytotoxicity and acute toxicity of the new compounds were negligible. The results show the usefulness of laccase for the synthesis of potential new antibiotics. The biological activity of the new compounds stimulates intensified pharmacological tests.

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Section: Resultssupporting

confidence: 89%

Section: Resultssupporting

confidence: 64%

Novel Cephalosporins Synthesized by Amination of 2,5-Dihydroxybenzoic Acid Derivatives Using Fungal Laccases II

Mikolasch

Niedermeyer

Lalk

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…HMBC spectra measured in DMSO showed two typical correlations for quinones in the range of 180 ppm. This is an important indication for the quinonoid character of 3a to 3e, confirming the oxidation of catechols to quinones similar to the hybrid dimer quinones formed from 2,5-dihydroxybenzoic acid derivatives with penicillins, 2) amino acids, 26) and primary aromatic amines, 27,28) and for the hybrid dimer quinones produced from 3,4-dichloraniline with protocatechuic acid and syringic acid. 24,29) Although 3a to 3e have quinone units as an element of the C-7 or C-6 substituent instead of catechol units these products should also have biological activity because of the described activities of other ortho-quinonoid [30][31][32] or para-quinonoid [33][34][35] substances.…”

Section: Resultssupporting

confidence: 60%

“…Reaction kinetics similar to these findings were described for hybrid dimer formation from 3,4-dichloroaniline and syringic acid 24) or 3-(3,4-dihydroxy-phenyl)-propionic acid and 4-aminobenzoic acid. 25) In contrast, for hybrid dimer formation from 2,5-dihydroxybenzoic acid derivatives with aminopenicillins and aminocephalosporins, 2,3) amino acids, 26) and primary aromatic amines, 27,28) we found straightforward biotransformations. Therefore the amination of 2,5-dihydroxybenzoic acid derivatives with laccase from Trametes sp.…”

Section: Resultsmentioning

confidence: 68%

Novel .BETA.-Lactam Antibiotics Synthesized by Amination of Catechols Using Fungal Laccase

et al. 2008

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In preceding papers, we discussed the laccase-catalyzed amination of 2,5-dihydroxybenzoic acid derivatives with aminopenicillins and aminocephalosporins.2,3) The motive for our work was the global issue with resistant pathogenic bacteria, e.g. Streptococcus pneumoniae strains [4][5][6][7] and Staphylococcus strains, against currently available b-lactam antibiotics. [8][9][10][11] Aminated products like 2-(3,6-dioxocyclohexa-1,4-dienylamino)-2-phenyl-acetylamino-penicillanic acids and 2-(3,6-dioxocyclohexa-1,4-dienylamino)-2-phenyl-acetylamino-cephalosporanic acids 2,3) inhibited the growth of several Gram positive bacterial strains and protected mice against an infection with Staphylococcus aureus. After amination the 2,5-dihydroxybenzoic acid derivatives were units of the C-7 substituent of the b-lactam antibiotics.The possibility of utilizing catechol units as an element of the C-7 substituent of penicillins and cephalosporins was investigated for a long time. [12][13][14][15][16][17] Through the tonB dependent iron transport mechanism, 18) the use of catechol substituted b-lactams was known to increase the drug's penetration into the bacterial cell walls. Thus, several catechol-substituted blactams have been synthesized and showed good antimicrobial activities. [19][20][21][22][23] As a consequence of the promising activity of the catechol substituted b-lactams on one hand and the novel laccase-synthesized b-lactams on the other hand, we got interested in laccase-catalyzed amination of catechols with aminopenicillins and aminocephalosporins.In this study, we have employed laccase from Trametes sp. to derivatize amino-b-lactams and to couple them both with catechol and with substituted catechols. The novel b-lactams were structurally characterized as new coupling products inhibiting the growth of several Gram positive bacterial strains in the agar diffusion assay, among them methicillin-resistant Staphylococcus aureus and vancomycin-resistant Enterococci. The cytotoxicity of the new compounds and the effectiveness in a "Staphylococcus-infected, immune suppressed mouse" model are discussed. Results and DiscussionBiotransformation of Amino-b b-lactams by LaccasesLaccase-catalyzed reaction between catechols (substrates 1a to 1c) on one hand and the amino-b-lactams cefadroxil 2a, amoxicillin 2b, ampicillin 2c, and the structurally related carbacephem loracarbef 2d on the other hand led to cross coupled products (Table 1). 3-Methylcatechol and amino-b-lactams were consumed after an incubation time of 1.5 h, and monoaminated products (3a to 3d) were detectable by high-performance liquid chromatography (HPLC). If other catechols or longer reaction times were used, monoaminated products were only obtained in low yields and undesirable side reactions produced a number of by-products. Reaction kinetics similar to these findings were described for hybrid dimer formation from 3,4-dichloroaniline and syringic acid 24) or 3-(3,4-dihydroxy-phenyl)-propionic acid and 4-aminobenzoic acid. 25) In contrast, for hybrid dimer form...

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“…However, during HPLC-MS analysis performed 20 min after dissolution the occurrence of the hydroquinone form of the products is already detectable in solvents like methanol as we reported previously for other amination products of 2,5-dihydroxybenzoic acid derivatives. 23) More specifically 1 H-NMR spectral data of 3a contained the characteristic signals for both substrate 1a and compound 2a. The number of CH proton signals of the dihydroxylated phenyl rings changed from three-in the substrate-to two signals-in the product.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of New N-Analogous Corollosporine Derivatives with Antibacterial Activity by Laccase-Catalyzed Amination

Mikolasch

Hessel

Salazar

et al. 2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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Corollosporine isolated from the marine fungus Corollospora maritima and N-analogous corollosporines are antimicrobial substances. Owing to the basic structure of the N-analogous corollosporines, they have become an attractive target for laccase-catalyzed derivatisation. In this regard we report on the straightforward laccase-catalyzed amination of dihydroxylated arenes with N-analogous corollosporines. In biological assays the obtained amination products are more active than the parent compounds.

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Laccase-induced derivatization of unprotected amino acid L-tryptophan by coupling with p-hydroquinone 2,5-dihydroxy-N-(2-hydroxyethyl)-benzamide

Cited by 36 publications

References 51 publications

Novel Cephalosporins Synthesized by Amination of 2,5-Dihydroxybenzoic Acid Derivatives Using Fungal Laccases II

Novel Cephalosporins Synthesized by Amination of 2,5-Dihydroxybenzoic Acid Derivatives Using Fungal Laccases II

Novel .BETA.-Lactam Antibiotics Synthesized by Amination of Catechols Using Fungal Laccase

Synthesis of New N-Analogous Corollosporine Derivatives with Antibacterial Activity by Laccase-Catalyzed Amination

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