Identification of a plausible biosynthetic enzyme for the IM-2-type autoregulator in Streptomyces antibioticus

Shikura, Noriyasu; Nihira, Takuya; Yamada, Yasuhiro

doi:10.1016/s0304-4165(00)00085-4

Cited by 4 publications

(9 citation statements)

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“…6-Dehydro-VB-A reductase activity was assayed at 25°C by using buffer A (without EDTA-Na 2 [pH 7.5]) containing 0.5 M NaCl as described previously (31,32). One unit of enzyme activity is defined as the amount of enzyme necessary to produce 1 mol of VB-A per min at 25°C.…”

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confidence: 99%

“…Reaction progress was followed intermittently, and the catalytic rate was calculated from the linear part of each reaction. The enzyme reaction was initiated as described previously (31,32) in a total volume of 575 l and was terminated by adding 200 l of 1% trifluoroacetic acid and 1,225 l of cold water. Five micrograms of racemic VB-D was added as an internal standard.…”

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confidence: 99%

“…The 75% CH 3 CN fraction was evaporated to dryness. The lyophilized sample was benzoylated with benzoyl cyanide and trin-butylamine as described previously (31,32). The benzoylation mixture was extracted with 4 ml of hexane-methanol-water (3 ml-250 l-750 l), and the organic layer containing both VB dibenzoate and VB-D dibenzoate was evaporated to dryness.…”

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barS1, a Gene for Biosynthesis of a γ-Butyrolactone Autoregulator, a Microbial Signaling Molecule Eliciting Antibiotic Production inStreptomycesSpecies

2002

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From Streptomyces virginiae, in which production of streptogramin antibiotic virginiamycin M 1 and S is tightly regulated by a low-molecular-weight Streptomyces hormone called virginiae butanolide (VB), which is a member of the ␥-butyrolactone autoregulators, the hormone biosynthetic gene (barS1) was cloned and characterized by heterologous expression in Escherichia coli and by gene disruption in S. virginiae. The barS1 gene (a 774-bp open reading frame encoding a 257-amino-acid protein [M r , 27,095]) is situated in the 10-kb regulator island surrounding the VB-specific receptor gene, barA. The deduced BarS1 protein is weakly homologous to ␤-ketoacyl-acyl carrier protein/coenzyme A reductase and belongs to the superfamily of short-chain alcohol dehydrogenase. The function of the BarS1 protein in VB biosynthesis was confirmed by BarS1-dependent in vitro conversion of 6-dehydro-VB-A to VB-A, the last catalytic step in VB biosynthesis. Of the four possible enantiomeric products from racemic 6-dehydro-VB-A as a substrate, only the natural enantiomer of (2R,3R,6S)-VB-A was produced by the purified recombinant BarS1 (rBarS1), indicating that rBarS1 is the stereospecific reductase recognizing (3R)-isomer as a substrate and reducing it stereospecifically to the (6S) product. In the ⌬barS1 mutant created by homologous recombination, the production of VB as well as the production of virginiamycin was lost. The production of virginiamycin by the ⌬barS1 mutant was fully recovered by the external addition of VB to the culture, which indicates that the barS1 gene is essential in the biosynthesis of the autoregulator VBs in S. virginiae and that the failure of virginiamycin production was a result of the loss of VB production.

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barS1, a Gene for Biosynthesis of a γ-Butyrolactone Autoregulator, a Microbial Signaling Molecule Eliciting Antibiotic Production inStreptomycesSpecies

2002

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“…1,2 "Streptomycetes" são bactérias Gram-positivas, caracterizadas pela capacidade de produzir uma grande variedade de metabólitos secundários, entre eles numerosos tipos de antibióticos comerciais e substâncias biologicamente ativas. 3,4 Todos os organismos necessitam produzir energia e alterar um grande número de compostos orgânicos, para poderem sobreviver, crescer e reproduzir. Isto é realizado através de um processo integrado de enzimas e reações químicas específicas, denominado metabolismo, sendo que os caminhos envolvidos são chamados de vias metabólicas.…”

Section: I1 As Bactérias Streptomyces E Os Fatores Autoreguladoresunclassified

“…Em bactérias da espécie Streptomyces, alguns compostos de baixo peso molecular, denominados fatores autoreguladores ou butirolactonas autoreguladoras, controlam essa produção. 3 De acordo com o mecanismo de ação, ainda não totalmente esclarecido, essas moléculas ligam-se a proteínas específicas que regulam a expressão de genes responsáveis pela síntese de determinados antibióticos. 5 Até o momento, cerca de uma dezena dessas butirolactonas autoreguladoras…”

Section: I1 As Bactérias Streptomyces E Os Fatores Autoreguladoresunclassified

Estudos sobre a síntese de butirolactonas auto-reguladoras de bactérias Streptomyces.

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À minha grande amiga Erika, pela cumplicidade em todos os momentos, pelas discussões, sugestões, carinho, sinceridade e pela ótima convivência desde a graduação, iniciação científica até a conclusão deste trabalho; Ao meu grande amigo Kleber, pela convivência, amizade e contribuição neste trabalho; À Mércia, pela sincera amizade, dedicação, consideração e pelas análises de HPLC; À Virginia, pela amizade e incontestável competência na obtenção dos espectros de RMN; À Cristina, pelas análises de GC/MS; Ao Djalma, pela amizade e pelos espectros de IV; Aos amigos do LSO: Aline, Valquíria, Adriana, Rosângela, Susi, Juliana, Ana Lúcia, Felipe, Gilberto, Miro, Álvaro, Ricardo, Paulo, Valdemar, Adilson, Luis Carlos, Francisco, Marco Antônio, Shirley, Emílio, Giovanna, Vinícius, Daiane, Ellen, Roberta, Rodrigo (Pena), Rodrigo, Viviani e Edilene; Algumas abreviações......................................................................................................1 Resumo............................................................................................................................3 Summary..........................................................................................................................5 I. Introdução....................................................................................................................7 II. Objetivos...................................................................................................................21 III. Planejamento Sintético............................................................................................23 IV. Atividades Realizadas e Resultados Obtidos...........................................................27 V. Conclusões................................................................................................................77 VI. Parte Experimental..................................................................................................80 VII. Espectros Selecionados........................................................................................125 VIII. Referências Bibliográficas..................................................................................199 A maioria desses compostos com propriedades autoreguladoras possui como característica estrutural comum a presença de um esqueleto γ-butirolactônico 2,3-dissubstituído, mas mostram pequenas diferenças estruturais na cadeia lateral.Essas moléculas, cujas estruturas são mostradas abaixo, são classificadas nos tipos:"virginiae" butanolidas (VB) A-E (1-5), fatores de Gräfe (6-7), butanolida IM-2 (8), o fator-I (9) e o fator-A (10). Gräfe's factors (6-7), IM-2 butanolide (8), I-factor (9) and A-factor (10). VB-B (2)OH VB-B (2)OHIn this work, studies were developed with aim to test a new synthetic pathway to obtain A-factor (10) analogous, which by enantioselective reduction of the carbonyl group of the side chain can be converted into others butyrolactone autoregulators. Summary Estudos sobre a síntese de butirolactona...

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Synthesis of (+) and (‐)‐Streptomyces coelicolor Butanolide 5 (SCB‐5)

Donges

Hofmann

Brüggemann³

et al. 2021

Eur J Org Chem

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Various 1-(1-hydroxyalkyl) paraconyl alcohols are important signaling molecules within antibiotics production in Streptomyces sp. Intending developing a flexible convergent chemical synthesis of such butanolides, a zwitterionic aza-Claisen rearrangement was chosen as reliable strategy generating the central stereotriad. Reaction of enantiopure N-allyl pyrrolidines and 4-phenylbutenoic acid fluoride delivered defined configured amides displaying the 2,3,1' stereotriads. The configuration was determined by the allyl alcohol moiety indicating a complete remote stereo control. Amide removal by iodolactonization and proceeding reductions, halocyclization and elimination gave key alkylidene tetrahydrofuran derivatives. Stepwise degradation of the olefins through ozonolysis, reductive workup and protecting group removal delivered both enantiomers of the target Streptomyces coelicolor butanolide 5.

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Identification of a plausible biosynthetic enzyme for the IM-2-type autoregulator in Streptomyces antibioticus

Cited by 4 publications

References 18 publications

barS1, a Gene for Biosynthesis of a γ-Butyrolactone Autoregulator, a Microbial Signaling Molecule Eliciting Antibiotic Production inStreptomycesSpecies

barS1, a Gene for Biosynthesis of a γ-Butyrolactone Autoregulator, a Microbial Signaling Molecule Eliciting Antibiotic Production inStreptomycesSpecies

Estudos sobre a síntese de butirolactonas auto-reguladoras de bactérias Streptomyces.

Synthesis of (+) and (‐)‐Streptomyces coelicolor Butanolide 5 (SCB‐5)

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