Fluostatin A
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| Category | Enzyme inhibitors |
| Catalog number | BBF-01423 |
| CAS | 160219-74-9 |
| Molecular Weight | 306.27 |
| Molecular Formula | C18H10O5 |
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Description
Fluostatin A is produced by the strain of Streptomyces sp. TA-3391. It inhibits the ability of DPP-III, and with arginyl-arginine-2-naphthalene formamide as the substrate, the IC50 is 0.44μg/mL.
Specification
| IUPAC Name | 6,7-dihydroxy-3-methylbenzo[a]fluorene-1,4,11-trione |
| Canonical SMILES | CC1=CC(=O)C2=C3C(=C(C=C2C1=O)O)C4=C(C3=O)C=CC=C4O |
| InChI | InChI=1S/C18H10O5/c1-7-5-11(20)14-9(17(7)22)6-12(21)15-13-8(18(23)16(14)15)3-2-4-10(13)19/h2-6,19,21H,1H3 |
| InChI Key | ISHOMJGAOPXCEF-UHFFFAOYSA-N |
Reference Reading
1. Heterologous Expression of Fluostatin Gene Cluster Leads to a Bioactive Heterodimer
Chunfang Yang, Chunshuai Huang, Wenjun Zhang, Yiguang Zhu, Changsheng Zhang Org Lett. 2015 Nov 6;17(21):5324-7. doi: 10.1021/acs.orglett.5b02683. Epub 2015 Oct 14.
The biosynthesis gene cluster (fls) for atypical angucycline fluostatins was identified from the marine derived Micromonospora rosaria SCSIO N160 and was confirmed by gene knockouts and the biochemical characterization of a bifunctional oxygenase FlsO2. The absolute configuration of the key biosynthetic intermediate prejadomycin was determined for the first time by Cu Kα X-ray analysis. Heterologous expression of the intact fls-gene cluster in Streptomyces coelicolor YF11 in the presence of 3% sea salts led to the isolation of two new compounds: fluostatin L (1) and difluostatin A (2). Difluostatin A (2), an unusual heterodimer, exhibited antibacterial activities.
2. Fluostatins A and B, new inhibitors of dipeptidyl peptidase III, produced by Streptomyces sp. TA-3391. I. Taxonomy of producing strain, production, isolation, physico-chemical properties and biological properties
T Akiyama, S Harada, F Kojima, Y Takahashi, C Imada, Y Okami, Y Muraoka, T Aoyagi, T Takeuchi J Antibiot (Tokyo). 1998 Jun;51(6):553-9. doi: 10.7164/antibiotics.51.553.
New inhibitors of dipeptidyl peptidaseIII (EC 3.4.14.4) from human placenta, designated as fluostatins A and B, were discovered in the fermentation broth of a strain isolated in our institute. The strain has been identified as Streptomyces sp. TA-3391 on the basis of taxonomic studies. Fluostatins A and B were purified by Diaion HP-20 chromatography, ethyl acetate extraction, silica gel chromatography and reverse phase preparative HPLC. With the synthetic substrate, arginyl-arginine-2-naphthylamide, the IC50 values of fluostatins A and B were 0.44 and 24.0 micrograms/ml, respectively. Fluostatins A and B were slightly inhibitory against other dipeptidyl peptidases. Fluostatin A showed mixed-type (competitive and noncompeptitive) inhibition with human leucine-enkephalin as a substrate, and the inhibition constant (Ki) was 14.2 microM.
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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 ╳
