Gougerotin
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| Category | Antibiotics |
| Catalog number | BBF-01275 |
| CAS | 2096-42-6 |
| Molecular Weight | 443.41 |
| Molecular Formula | C16H25N7O8 |
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Description
It is produced by the strain of Streptomyces gougerotii 21544. It has weak activity against gram-positive bacteria, negative bacteria and mycobacterium, and can inhibit Newcastle disease virus, vaccinia virus, pseudorabies virus and western equine encephalomyelitis virus.
Specification
| Synonyms | Antibiotic 21544; Asteromycin; 1-(4-Deoxy-4-(sarcosyl-D-seryl)amino-beta-D-glucopyranuronamide)cytosine; N(4)-Sarcosyl-1-(3'-deoxy-3'-D-serylamido-beta-D-allopyranosyluronamide)cytosine; Glucopyranuronamide, 1-(4-amino-2-oxo-1(2H)-pyrimidinyl)-1,4-dideoxy-4-(D-2-(2-(methylamino)acetamido)hydracrylamido)-, beta-D-; Aspiculamycin; Quingfengmycin |
| IUPAC Name | (2S,3S,4S,5R,6R)-6-(4-amino-2-oxopyrimidin-1-yl)-4,5-dihydroxy-3-[[(2R)-3-hydroxy-2-[[2-(methylamino)acetyl]amino]propanoyl]amino]oxane-2-carboxamide |
| Canonical SMILES | CNCC(=O)NC(CO)C(=O)NC1C(C(C(OC1C(=O)N)N2C=CC(=NC2=O)N)O)O |
| InChI | InChI=1S/C16H25N7O8/c1-19-4-8(25)20-6(5-24)14(29)22-9-10(26)11(27)15(31-12(9)13(18)28)23-3-2-7(17)21-16(23)30/h2-3,6,9-12,15,19,24,26-27H,4-5H2,1H3,(H2,18,28)(H,20,25)(H,22,29)(H2,17,21,30)/t6-,9+,10+,11-,12+,15-/m1/s1 |
| InChI Key | AMNAZJFEONUVTD-QJHHURCWSA-N |
Properties
| Appearance | Colorless Acicular Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; Mycobacteria; Viruses |
| Density | 1.82 g/cm3 |
| Solubility | Soluble in Water |
Reference Reading
1. [Functional characterization of gouC and gouD in gougerotin biosynthesis]
Junhong Wei, Jihui Zhang, Lingjuan Jiang, Huarong Tan, Guoqing Niu Wei Sheng Wu Xue Bao. 2016 Mar 4;56(3):406-17.
Objective: To determine the functions of gouC and gouD in gougerotin biosynthesis, disruption of these two genes was performed. As gougerotin producing strain Streptomyces graminearus lacks efficient genetic manipulation system, the gene cluster for gougerotin biosynthesis was heterologously expressed in Streptomyces coelicolor M1146 to facilitate genetic manipulations of gouC and gouD. Methods: By using fosmid D6-4H containing the complete gougerotin biosynthetic gene cluster, gouC and gouD were disrupted by PCR-targeting method to generate pGOUe-ΔC and pGOUe-ΔD. Both pGOUe-ΔC and pGOUe-ΔD were introduced into Streptomyces coelicolor M1146 by intergeneric conjugation, thus gouC and gouD disrpution mutants (Ml146-GOUe-AC and M1146-GOUe-ΔD) were obtained. The gougerotin production of M1146-GOUe-ΔC and M1146-GOUe-ΔD were assayed by HPLC analysis. The intermediates accumulated in these mutants were purified and subjected to MS and NMR analyses for structure determinations. Bioassay of these intermediates against tumor cell line were also carried out. Results: Disruption mutants of gouC and gouD failed to produce gougerotin and the mutants accumulated different gougerotin intermediates, which lost their ability to inhibit cancer cell proliferation. Conclusion: gouC and gouD are key structual genes in the biosynthesis of gougerotin peptidyl moieties. This study will pave the way for the elucidation of gougerotin biosynthetic pathway.
2. GouR, a TetR family transcriptional regulator, coordinates the biosynthesis and export of gougerotin in Streptomyces graminearus
Junhong Wei, Yuqing Tian, Guoqing Niu, Huarong Tan Appl Environ Microbiol. 2014 Jan;80(2):714-22. doi: 10.1128/AEM.03003-13. Epub 2013 Nov 15.
Gougerotin is a peptidyl nucleoside antibiotic. It functions as a specific inhibitor of protein synthesis by binding ribosomal peptidyl transferase and exhibits a broad spectrum of biological activities. gouR, situated in the gougerotin biosynthetic gene cluster, encodes a TetR family transcriptional regulatory protein. Gene disruption and genetic complementation revealed that gouR plays an important role in the biosynthesis of gougerotin. Transcriptional analysis suggested that GouR represses the transcription of the gouL-to-gouB operon consisting of 11 structural genes and activates the transcription of the major facilitator superfamily (MFS) transporter gene (gouM). Electrophoresis mobility shift assays (EMSAs) and DNase I footprinting experiments showed that GouR has specific DNA-binding activity for the promoter regions of gouL, gouM, and gouR. Our data suggested that GouR modulates gougerotin production by coordinating its biosynthesis and export in Streptomyces graminearus.
3. Improvement of gougerotin and nikkomycin production by engineering their biosynthetic gene clusters
Deyao Du, Yu Zhu, Junhong Wei, Yuqing Tian, Guoqing Niu, Huarong Tan Appl Microbiol Biotechnol. 2013 Jul;97(14):6383-96. doi: 10.1007/s00253-013-4836-7. Epub 2013 Mar 21.
Nikkomycins and gougerotin are peptidyl nucleoside antibiotics with broad biological activities. The nikkomycin biosynthetic gene cluster comprises one pathway-specific regulatory gene (sanG) and 21 structural genes, whereas the gene cluster for gougerotin biosynthesis includes one putative regulatory gene, one major facilitator superfamily transporter gene, and 13 structural genes. In the present study, we introduced sanG driven by six different promoters into Streptomyces ansochromogenes TH322. Nikkomycin production was increased significantly with the highest increase in engineered strain harboring hrdB promoter-driven sanG. In the meantime, we replaced the native promoter of key structural genes in the gougerotin (gou) gene cluster with the hrdB promoters. The heterologous producer Streptomyces coelicolor M1146 harboring the modified gene cluster produced gougerotin up to 10-fold more than strains carrying the unmodified cluster. Therefore, genetic manipulations of genes involved in antibiotics biosynthesis with the constitutive hrdB promoter present a robust, easy-to-use system generally useful for the improvement of antibiotics production in Streptomyces.
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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
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
