Chemistry:Sanglifehrin
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| Systematic IUPAC name
(3S,6S,9R,10R,11S,12S,13E,15E,18S,21S)-18-{(2E,4E,8S,9S)-10-[(2S,3R,4S,5S,6R,9S,11S)-9-Ethyl-4-hydroxy-3,5,11-trimethyl-8-oxo-1-oxa-7-azaspiro[5.5]undec-2-yl]-9-hydroxy-8-methyl-2,4-decadien-2-yl}-10, 12-dihydroxy-3-(3-hydroxybenzyl)-6-isopropyl-11-methyl-9-(3-oxobutyl)-19-oxa-1,4,7,25-tetraazabicyclo[19.3.1]pentacosa-13,15-diene-2,5,8,20-tetrone | |
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3D model (JSmol)
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PubChem CID
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| Properties | |
| C60H91N5O13 | |
| Molar mass | 1090.4 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Sanglifehrin A is a polyketide natural product found to potently inhibit cyclophilins and have immunosuppressive activity.[1]
History
Isolation and characterisation of Sanglifehrins, produced by fermentation of Streptomyces sp. A92-308110 was first published by JJ Sanglier and T Fehr in 1999.[2]
Structure
Sanglifehrins are mixed polyketide / non-ribosomal peptides, and their biosynthesis requires a modular type I polyketide synthase, with one module of non-ribosomal peptide synthetase, which incorporates phenylalanine, later converted by a hydroxylase to meta-tyrosine.[3]
See also
- Rapamycin
- Epothilone
References
- ↑ Zenke, G.; Strittmatter, U.; Fuchs, S.; Quesniaux, V. F.; Brinkmann, V.; Schuler, W.; Zurini, M.; Enz, A. et al. (2001). "Sanglifehrin A, a novel cyclophilin-binding compound showing immunosuppressive activity with a new mechanism of action". Journal of Immunology 166 (12): 7165–7171. doi:10.4049/jimmunol.166.12.7165. PMID 11390463.
- ↑ Sanglier, J. J.; Quesniaux, V.; Fehr, T.; Hofmann, H.; Mahnke, M.; Memmert, K.; Schuler, W.; Zenke, G. et al. (1999). "Sanglifehrins A, B, C and D, novel cyclophilin-binding compounds isolated from Streptomyces sp. A92-308110. I. Taxonomy, fermentation, isolation and biological activity". The Journal of Antibiotics 52 (5): 466–473. doi:10.7164/antibiotics.52.466. PMID 10480570.
- ↑ Qu, X.; Jiang, N.; Xu, F.; Shao, L.; Tang, G.; Wilkinson, B.; Liu, W. (2011). "Cloning, sequencing and characterization of the biosynthetic gene cluster of sanglifehrin A, a potent cyclophilin inhibitor". Molecular BioSystems 7 (3): 852–861. doi:10.1039/c0mb00234h. PMID 21416665. https://pubmed.ncbi.nlm.nih.gov/21416665/.
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