Goadsporin
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| Category | Others |
| Catalog number | BBF-01274 |
| CAS | 883434-90-0 |
| Molecular Weight | 1612.78 |
| Molecular Formula | C72H97N19O20S2 |
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Description
It is produced by the strain of Streptomyces sp. TP-A0584. It can promote the secondary metabolism and morphogenesis of Streptomyces, and it is a tool to analyze the regulatory mechanism of Streptomyces.
Properties
| Appearance | Colorless Powder |
| Melting Point | 172-174 °C |
| Solubility | Soluble in Methanol |
Reference Reading
1. Dissection of goadsporin biosynthesis by in vitro reconstitution leading to designer analogues expressed in vivo
Taro Ozaki, Kona Yamashita, Yuki Goto, Morito Shimomura, Shohei Hayashi, Shumpei Asamizu, Yoshinori Sugai, Haruo Ikeda, Hiroaki Suga, Hiroyasu Onaka Nat Commun. 2017 Feb 6;8:14207. doi: 10.1038/ncomms14207.
Goadsporin (GS) is a member of ribosomally synthesized and post-translationally modified peptides (RiPPs), containing an N-terminal acetyl moiety, six azoles and two dehydroalanines in the peptidic main chain. Although the enzymes involved in GS biosynthesis have been defined, the principle of how the respective enzymes control the specific modifications remains elusive. Here we report a one-pot synthesis of GS using the enzymes reconstituted in the 'flexible' in vitro translation system, referred to as the FIT-GS system. This system allows us to readily prepare not only the precursor peptide from its synthetic DNA template but also 52 mutants, enabling us to dissect the modification determinants of GodA for each enzyme. The in vitro knowledge has also led us to successfully produce designer GS analogues in vivo. The methodology demonstrated in this work is also applicable to other RiPP biosynthesis, allowing us to rapidly investigate the principle of modification events with great ease.
2. Novel antibiotic screening methods to awaken silent or cryptic secondary metabolic pathways in actinomycetes
Hiroyasu Onaka J Antibiot (Tokyo). 2017 Jul;70(8):865-870. doi: 10.1038/ja.2017.51. Epub 2017 Apr 26.
Streptomyces have the potential to produce more than 30 secondary metabolites; however, the expression of most metabolite biosynthetic gene clusters is cryptic or silent. Indeed, the expression of these genes is conditional and dependent on culture conditions. To activate such gene clusters, many methods have been developed. In this review, I describe two activation approaches developed in my laboratory: use of the activation mediator goadsporin and combined-culture. Goadsporin is a chemical substance isolated from Streptomyces sp. TP-A0584; it induces secondary metabolism and sporulation of many Streptomyces species. Combined-culture is a co-culture method to activate secondary metabolism in Streptomyces. The activator strains are mycolic acid-containing bacteria and ~90% of Streptomyces species show changes in secondary metabolism in combined-culture compared with pure culture. Thus, both methods may have applications in natural product-based drug discovery.
3. Total Synthesis of the Post-translationally Modified Polyazole Peptide Antibiotic Goadsporin
Hannah L Dexter, Huw E L Williams, William Lewis, Christopher J Moody Angew Chem Int Ed Engl. 2017 Mar 6;56(11):3069-3073. doi: 10.1002/anie.201612103. Epub 2017 Feb 1.
The structurally unique polyazole antibiotic goadsporin contains six heteroaromatic oxazole and thiazole rings integrated into a linear array of amino acids that also contains two dehydroalanine residues. An efficient total synthesis of goadsporin is reported in which the key steps are the use of rhodium(II)-catalyzed reactions of diazocarbonyl compounds to generate the four oxazole rings, which demonstrates the power of rhodium carbene chemistry in organic chemical synthesis.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
