Glidobactin A
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Bioactive by-products |
| Catalog number | BBF-00212 |
| CAS | 108351-50-4 |
| Molecular Weight | 520.66 |
| Molecular Formula | C27H44N4O6 |
Online Inquiry
Description
Glidobactin A is an acyl peptide antibiotic produced by Pseudomonas sp. CB-3. It has activity against Candida, Aspergillus fumigatus and Trichophyton, but it is not effective against Candida albicans M-9 infection in mice.
Specification
| Synonyms | Cepafungin II |
| IUPAC Name | (2E,4E)-N-[(2S,3R)-3-hydroxy-1-[[(3Z,5S,8S,10S)-10-hydroxy-5-methyl-2,7-dioxo-1,6-diazacyclododec-3-en-8-yl]amino]-1-oxobutan-2-yl]dodeca-2,4-dienamide |
| Canonical SMILES | CCCCCCCC=CC=CC(=O)NC(C(C)O)C(=O)NC1CC(CCNC(=O)C=CC(NC1=O)C)O |
| InChI | InChI=1S/C27H44N4O6/c1-4-5-6-7-8-9-10-11-12-13-24(35)31-25(20(3)32)27(37)30-22-18-21(33)16-17-28-23(34)15-14-19(2)29-26(22)36/h10-15,19-22,25,32-33H,4-9,16-18H2,1-3H3,(H,28,34)(H,29,36)(H,30,37)(H,31,35)/b11-10+,13-12+,15-14-/t19-,20+,21-,22-,25-/m0/s1 |
| InChI Key | TYGJUQYJMIOZLZ-QQXADAIISA-N |
Properties
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 892.9°C at 760 mmHg |
| Melting Point | 245-250°C |
| Density | 1.16 g/cm3 |
Reference Reading
1. Evaluation of the Antifungal Activities of Photorhabdus akhurstii and Its Secondary Metabolites against Phytopathogenic Colletotrichum gloeosporioides
Po-Wen Tu, Jie-Siang Chiu, Chih Lin, Chih-Cheng Chien, Feng-Chia Hsieh, Ming-Che Shih, Yu-Liang Yang J Fungi (Basel). 2022 Apr 15;8(4):403. doi: 10.3390/jof8040403.
Colletotrichum gloeosporioides is a phytopathogenic fungus that causes devastating losses in strawberries without effective countermeasures. Members of the genus Photorhabdus exhibit antimicrobial capability and have been found to have the potential for use as biocontrol agents against C. gloeosporioides. Photorhabdus species exhibit two phase variations with a differentiated composition of secondary metabolites designated to each phase. In this study, Photorhabdus akhurstii sp. nov. 0813-124 exhibited phase I (PL1) and phase II (PL2); however, only PL1 displayed distinct inhibition of C. gloeosporioides in the confrontation assay. We identified the bioactive ingredients of P. akhurstii sp. nov. 0813-124 to be glidobactin A and cepafungin I, with MIC values lower than 1.5 and 2.0 µg/mL, respectively. Furthermore, we revealed the biosynthetic gene cluster (BGC) of corresponding bioactive molecules through genomics analysis and determined its expression level in PL1 and PL2. The expression of glidobactin BGC in PL1 increased rapidly within 24 h, while PL2 was eventually stimulated after 60 h. In summary, we demonstrated that P. akhurstii sp. nov. 0813-124 could potentially be used as a biocontrol agent or part of a natural product repertoire for combating C. gloeosporioides.
2. Activation, Structure, Biosynthesis and Bioactivity of Glidobactin-like Proteasome Inhibitors from Photorhabdus laumondii
Lei Zhao, Camille Le Chapelain, Alexander O Brachmann, Marcel Kaiser, Michael Groll, Helge B Bode Chembiochem. 2021 May 4;22(9):1582-1588. doi: 10.1002/cbic.202100014. Epub 2021 Mar 3.
The glidobactin-like natural products (GLNPs) glidobactin A and cepafungin I have been reported to be potent proteasome inhibitors and are regarded as promising candidates for anticancer drug development. Their biosynthetic gene cluster (BGC) plu1881-1877 is present in entomopathogenic Photorhabdus laumondii but silent under standard laboratory conditions. Here we show the largest subset of GLNPs, which are produced and identified after activation of the silent BGC in the native host and following heterologous expression of the BGC in Escherichia coli. Their chemical diversity results from a relaxed substrate specificity and flexible product release in the assembly line of GLNPs. Crystal structure analysis of the yeast proteasome in complex with new GLNPs suggests that the degree of unsaturation and the length of the aliphatic tail are critical for their bioactivity. The results in this study provide the basis to engineer the BGC for the generation of new GLNPs and to optimize these natural products resulting in potential drugs for cancer therapy.
3. Stepwise genetic engineering of Pseudomonas putida enables robust heterologous production of prodigiosin and glidobactin A
Taylor B Cook, Tyler B Jacobson, Maya V Venkataraman, Heike Hofstetter, Daniel Amador-Noguez, Michael G Thomas, Brian F Pfleger Metab Eng. 2021 Sep;67:112-124. doi: 10.1016/j.ymben.2021.06.004. Epub 2021 Jun 24.
Polyketide synthases (PKS) and nonribosomal peptide synthetases (NRPS) comprise biosynthetic pathways that provide access to diverse, often bioactive natural products. Metabolic engineering can improve production metrics to support characterization and drug-development studies, but often native hosts are difficult to genetically manipulate and/or culture. For this reason, heterologous expression is a common strategy for natural product discovery and characterization. Many bacteria have been developed to express heterologous biosynthetic gene clusters (BGCs) for producing polyketides and nonribosomal peptides. In this article, we describe tools for using Pseudomonas putida, a Gram-negative soil bacterium, as a heterologous host for producing natural products. Pseudomonads are known to produce many natural products, but P. putida production titers have been inconsistent in the literature and often low compared to other hosts. In recent years, synthetic biology tools for engineering P. putida have greatly improved, but their application towards production of natural products is limited. To demonstrate the potential of P. putida as a heterologous host, we introduced BGCs encoding the synthesis of prodigiosin and glidobactin A, two bioactive natural products synthesized from a combination of PKS and NRPS enzymology. Engineered strains exhibited robust production of both compounds after a single chromosomal integration of the corresponding BGC. Next, we took advantage of a set of genome-editing tools to increase titers by modifying transcription and translation of the BGCs and increasing the availability of auxiliary proteins required for PKS and NRPS activity. Lastly, we discovered genetic modifications to P. putida that affect natural product synthesis, including a strategy for removing a carbon sink that improves product titers. These efforts resulted in production strains capable of producing 1.1 g/L prodigiosin and 470 mg/L glidobactin A.
Recommended Products
| BBF-00764 | Cerebroside C | Inquiry |
| BBF-01829 | Deoxynojirimycin | Inquiry |
| BBF-03755 | Actinomycin D | Inquiry |
| BBF-02614 | Nystatin | Inquiry |
| BBF-03754 | CASTANOSPERMINE | Inquiry |
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
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
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
