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https://www.readbyqxmd.com/read/27410522/skfb-abstracts-a-hydrogen-atom-from-c%C3%AE-on-skfa-to-initiate-thioether-cross-link-formation
#1
Nathan A Bruender, Vahe Bandarian
Sulfur to α-carbon thioether-containing peptides (sactipeptides) are ribosomally synthesized post-translationally modified peptides with bacteriocidal activities. The thioether cross-link, which is required for biological activity, is installed by a member of the radical S-adenosyl-l-methionine (SAM) superfamily in the peptide substrate. Herein, we show that the radical SAM enzyme, SkfB, utilizes the 5'-deoxyadenosyl radical generated from the reductive cleavage of SAM to abstract a hydrogen atom from the α-carbon of the amino acid at position 12 in the substrate, SkfA, to initiate the installation of a thioether cross-link...
August 2, 2016: Biochemistry
https://www.readbyqxmd.com/read/27019323/production-of-sactipeptides-in-escherichia-coli-probing-the-substrate-promiscuity-of-subtilosin-a-biosynthesis
#2
Paul M Himes, Scott E Allen, Sungwon Hwang, Albert A Bowers
Sactipeptides are peptide-derived natural products that are processed by remarkable, radical-mediated cysteine sulfur to α-carbon coupling reactions. The resulting sactionine thioether linkages give rise to the unique defined structures and concomitant biological activities of sactipeptides. An E. coli heterologous expression system, based on the biosynthesis of one such sactipeptide, subtilosin A, is described and this expression system is exploited to probe the promiscuity of the subtilosin A sactionine bond-forming enzyme, AlbA...
June 17, 2016: ACS Chemical Biology
https://www.readbyqxmd.com/read/26377179/in-silico-identification-of-bacteriocin-gene-clusters-in-the-gastrointestinal-tract-based-on-the-human-microbiome-project-s-reference-genome-database
#3
Calum J Walsh, Caitriona M Guinane, Colin Hill, R Paul Ross, Paul W O'Toole, Paul D Cotter
BACKGROUND: The human gut microbiota comprises approximately 100 trillion microbial cells which significantly impact many aspects of human physiology - including metabolism, nutrient absorption and immune function. Disturbances in this population have been implicated in many conditions and diseases, including obesity, type-2 diabetes and inflammatory bowel disease. This suggests that targeted manipulation or shaping of the gut microbiota, by bacteriocins and other antimicrobials, has potential as a therapeutic tool for the prevention or treatment of these conditions...
2015: BMC Microbiology
https://www.readbyqxmd.com/read/26253660/distribution-and-genetic-diversity-of-bacteriocin-gene-clusters-in-rumen-microbial-genomes
#4
Analice C Azevedo, Cláudia B P Bento, Jeronimo C Ruiz, Marisa V Queiroz, Hilário C Mantovani
Some species of ruminal bacteria are known to produce antimicrobial peptides, but the screening procedures have mostly been based on in vitro assays using standardized methods. Recent sequencing efforts have made available the genome sequences of hundreds of ruminal microorganisms. In this work, we performed genome mining of the complete and partial genome sequences of 224 ruminal bacteria and 5 ruminal archaea to determine the distribution and diversity of bacteriocin gene clusters. A total of 46 bacteriocin gene clusters were identified in 33 strains of ruminal bacteria...
October 2015: Applied and Environmental Microbiology
https://www.readbyqxmd.com/read/26026269/the-pqqd-homologous-domain-of-the-radical-sam-enzyme-thnb-is-required-for-thioether-bond-formation-during-thurincin-h-maturation
#5
Beata M Wieckowski, Julian D Hegemann, Andreas Mielcarek, Linda Boss, Olaf Burghaus, Mohamed A Marahiel
Thurincin H is a 31-residue, ribosomally synthesized bacteriocin originating from the thn operon of Bacillus thuringiensis SF361. It is the only known sactipeptide carrying four thioether bridges between four cysteines and the α-carbons of a serine, an asparagine and two threonine residues. By analysis of the thn operon and use of in vitro studies we now reveal that ThnB is a radical S-adenosylmethionine (SAM) enzyme containing two [4Fe-4S] clusters. Furthermore, we confirm the involvement of ThnB in the formation of the thioether bonds present within the structure of thurincin H...
July 8, 2015: FEBS Letters
https://www.readbyqxmd.com/read/25844528/substrate-controlled-stereochemistry-in-natural-product-biosynthesis
#6
REVIEW
Wei Ding, Yongzhen Li, Qi Zhang
Enzymes are generally believed to be highly regio- and stereoselective catalysts that strictly control the reaction coordinates and dominate the final catalytic outcomes. However, recent studies have started to suggest that substrates sometimes play key roles in determining the product selectivity in enzyme catalysis. Here, we highlight several enzymatic reactions in which the stereoselectivity is, at least in large part, governed by the intrinsic properties of the substrate rather than by characteristics of the enzyme...
July 17, 2015: ACS Chemical Biology
https://www.readbyqxmd.com/read/23891473/radical-s-adenosylmethionine-enzyme-catalyzed-thioether-bond-formation-in-sactipeptide-biosynthesis
#7
REVIEW
Leif Flühe, Mohamed A Marahiel
Sactipeptides represent a new emerging class of ribosomally assembled and posttranslationally modified peptides that show diverse bioactivities. Their common hallmark is an intramolecular thioether bond that crosslink the sulfur atom of a cysteine residue with the α-carbon of an acceptor amino acid. This review summarizes recent achievements concerning the biosynthesis of sactipeptides in general and with special focus on the common enzymatic radical SAM mechanism leading to the thioether linkage formation...
August 2013: Current Opinion in Chemical Biology
https://www.readbyqxmd.com/read/23677608/bagel3-automated-identification-of-genes-encoding-bacteriocins-and-non-bactericidal-posttranslationally-modified-peptides
#8
Auke J van Heel, Anne de Jong, Manuel Montalbán-López, Jan Kok, Oscar P Kuipers
Identifying genes encoding bacteriocins and ribosomally synthesized and posttranslationally modified peptides (RiPPs) can be a challenging task. Especially those peptides that do not have strong homology to previously identified peptides can easily be overlooked. Extensive use of BAGEL2 and user feedback has led us to develop BAGEL3. BAGEL3 features genome mining of prokaryotes, which is largely independent of open reading frame (ORF) predictions and has been extended to cover more (novel) classes of posttranslationally modified peptides...
July 2013: Nucleic Acids Research
https://www.readbyqxmd.com/read/23282011/two-4fe-4s-clusters-containing-radical-sam-enzyme-skfb-catalyze-thioether-bond-formation-during-the-maturation-of-the-sporulation-killing-factor
#9
Leif Flühe, Olaf Burghaus, Beata M Wieckowski, Tobias W Giessen, Uwe Linne, Mohamed A Marahiel
The sporulation killing factor (SKF) is a 26-residue ribosomally assembled and posttranslationally modified sactipeptide. It is produced by Bacillus subtilis 168 and plays a key role in its sporulation. Like all sactipeptides, SKF contains a thioether bond, which links the cysteine residue Cys4 with the α-carbon of the methionine residue Met12. In this study we demonstrate that this bond is generated by the two [4Fe-4S] clusters containing radical SAM enzyme SkfB, which is encoded in the skf operon. By mutational analysis of both cluster-binding sites, we were able to postulate a mechanism for thioether generation which is in agreement with that of AlbA...
January 23, 2013: Journal of the American Chemical Society
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