Gregatin B
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| Names | |
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| IUPAC name
Methyl (5R)-5-[(1E,3E)-hexa-1,3-dienyl]-2,5-dimethyl-4-oxofuran-3-carboxylate[1] | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
PubChem CID |
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| Properties | |
| C14H18O4 | |
| Molar mass | 250.294 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Gregatin B is a metabolite of the fungi Cephalosporium gregatum and Aspergillus panamensis with the molecular formula C14H18O4[2][3] Gregatin B is a weak antibiotic.[4][3] Gregatin B was discovered in 1982[3] and has been the subject of total synthesis.[5][6]
References
[edit]- ↑ "Gregatin B". Pubchem.ncbi.NLM.nih.gov. Archived from the original on March 14, 2022.
- ↑ Durbin, R. (2 December 2012). Toxins in Plant Disease. Elsevier. p. 410. ISBN 978-0-323-14704-0.
- 1 2 3 Buckingham, John (1987). Dictionary of Organic Compounds. Taylor & Francis. p. 367. ISBN 978-0-412-17050-8.
- ↑ Bycroft, Barrie W.; Payne, David J. (9 August 2013). Dictionary of Antibiotics and Related Substances: with CD-ROM, Second Edition. CRC Press. p. 892. ISBN 978-1-4822-8215-3.
- ↑ "Gregatin B | Chemical Substance Information | J-GLOBAL". Jglobal.JST.go.jp.
- ↑ Kusakabe, Taichi; Kawai, Yasuko; Kato, Keisuke (4 October 2013). "Total Synthesis of (+)-Gregatin B and E". Organic Letters. 15 (19): 5102–5105. doi:10.1021/ol402472q. PMID 24066736.
Further reading
[edit]- Wijeratne, E. M. Kithsiri; Xu, Yaming; Arnold, A. Elizabeth; Gunatilaka, A. A. Leslie (January 2015). "Pulvinulin A, Graminin C, and cis-Gregatin B – New Natural Furanones from Pulvinula sp. 11120, a Fungal Endophyte of Cupressus arizonica". Natural Product Communications. 10 (1): 1934578X1501000. doi:10.1177/1934578x1501000127. ISSN 1934-578X. S2CID 39340804.
- Burghart-Stoll, H; Brückner, R (20 May 2011). "A serendipitous synthesis of (+)-gregatin B, second structure revisions of the aspertetronins, gregatins, and graminin A, structure revision of the penicilliols". Organic Letters. 13 (10): 2730–3. doi:10.1021/ol2008318. PMID 21526752.
- Peberdy, John F. (11 November 2013). Penicillium and Acremonium. Springer Science & Business Media. p. 222. ISBN 978-1-4899-1986-1.