FD-594
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| Category | Antibiotics |
| Catalog number | BBF-02837 |
| CAS | |
| Molecular Weight | 940.93 |
| Molecular Formula | C47H56O20 |
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Description
FD-594 is produced by the strain of Streptomyces sp. TA-0256. It showed similar or slightly weaker cytotoxicity to adriamycin against HL-60, P388, L1210, HeLa and A549 cells, and moderate antibacterial activity against Gram-positive bacteria.
Specification
| IUPAC Name | 3,12,13,22,26-pentahydroxy-21-[(2S,4R,5S,6R)-4-hydroxy-5-[(2S,4R,5S,6R)-4-hydroxy-5-[(2S,4R,5R,6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-15-methoxy-7-propyl-6,17-dioxahexacyclo[12.12.0.02,11.04,9.016,25.018,23]hexacosa-1(14),2(11),3,9,15,18(23),19,21,25-nonaene-5,24-dione |
| Canonical SMILES | CCCC1CC2=CC3=C(C4=C(C(C3O)O)C(=C5C(=C4O)C(=O)C6=C(O5)C=CC(=C6O)OC7CC(C(C(O7)C)OC8CC(C(C(O8)C)OC9CC(C(C(O9)C)O)OC)O)O)OC)C(=C2C(=O)O1)O |
| InChI | InChI=1S/C47H56O20/c1-7-8-20-11-19-12-21-31(39(53)30(19)47(57)63-20)33-34(42(56)37(21)51)45(59-6)46-35(41(33)55)40(54)32-24(65-46)9-10-25(38(32)52)64-27-13-22(48)43(17(3)61-27)66-28-14-23(49)44(18(4)62-28)67-29-15-26(58-5)36(50)16(2)60-29/h9-10,12,16-18,20,22-23,26-29,36-37,42-44,48-53,55-56H,7-8,11,13-15H2,1-6H3/t16-,17-,18-,20?,22-,23-,26-,27+,28+,29+,36-,37?,42?,43-,44-/m1/s1 |
| InChI Key | AUXDHORIJUSTHY-SHXGDCNXSA-N |
Properties
| Appearance | Yellow Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; neoplastics (Tumor) |
| Melting Point | 199-202°C |
| Density | 1.6±0.1 g/cm3 |
Reference Reading
1. Biodiversity, Bioactivity, and Metabolites of High Desert Derived Oregonian Soil Bacteria
Chenxi Zhu, Cassandra I Lew, George F Neuhaus, Donovon A Adpressa, Lev N Zakharov, Elizabeth N Kaweesa, Birte Plitzko, Sandra Loesgen Chem Biodivers. 2021 Apr;18(4):e2100046. doi: 10.1002/cbdv.202100046. Epub 2021 Mar 24.
From arid, high desert soil samples collected near Bend, Oregon, 19 unique bacteria were isolated. Each strain was identified by 16S rRNA gene sequencing, and their organic extracts were tested for antibacterial and antiproliferative activities. Noteworthy, six extracts (30 %) exhibited strong inhibition resulting in less than 50 % cell proliferation in more than one cancer cell model, tested at 10 μg/mL. Principal component analysis (PCA) of LC/MS data revealed drastic differences in the metabolic profiles found in the organic extracts of these soil bacteria. In total, fourteen potent antibacterial and/or cytotoxic metabolites were isolated via bioactivity-guided fractionation, including two new natural products: a pyrazinone containing tetrapeptide and 7-methoxy-2,3-dimethyl-4H-chromen-4-one, as well as twelve known compounds: furanonaphthoquinone I, bafilomycin C1 and D, FD-594, oligomycin A, chloramphenicol, MY12-62A, rac-sclerone, isosclerone, tunicamycin VII, tunicamycin VIII, and (6S,16S)-anthrabenzoxocinone 1.264-C.
2. Cloning of the biosynthetic gene cluster for naphthoxanthene antibiotic FD-594 from Streptomyces sp. TA-0256
Fumitaka Kudo, Takanori Yonezawa, Akiko Komatsubara, Kazutoshi Mizoue, Tadashi Eguchi J Antibiot (Tokyo). 2011 Jan;64(1):123-32. doi: 10.1038/ja.2010.145. Epub 2010 Nov 24.
FD-594 is an unique pyrano[4',3':6,7]naphtho[1,2-b]xanthene polyketide with a trisaccharide of 2,6-dideoxysugars. In this study, we cloned the FD-594 biosynthetic gene cluster from the producer strain Streptomyces sp. TA-0256 to investigate its biosynthesis. The identified pnx gene cluster was 38143 bp, consisting of 40 open reading frames, including a minimal PKS gene, TDP-olivose biosynthetic genes, two glycosyltransferase genes, two methyltransferase genes and many oxygenase/reductase genes. Most of these enzymes coded in the pnx cluster were reasonably assigned to a plausible biosynthetic pathway for FD-594, in which an unique ring opening process via Baeyer-Villiger-type oxidation catalyzed by a putative flavin adenine dinucleotide (FAD)-dependent monooxygenase, is speculated to lead to the unique xanthene structure. To clarify the involvement of pnx genes in the FD-594 biosynthesis, a glycosyltransferase, PnxGT2, and a methyltransferase, PnxMT2, were characterized enzymatically with the recombinant proteins expressed in Escherichia coli. As a result, PnxGT2 catalyzed the triple olivose transfers to the FD-594 aglycon with TDP-olivose as the glycosyl donor to afford triolivoside. Surprisingly, in the PnxGT2 enzymatic reaction, tetraolivoside and pentaolivoside were significantly detected along with the expected triolivoside. To our knowledge, PnxGT2 is the first contiguous oligosaccharide-forming glycosyltransferase in secondary metabolism. Furthermore, addition of PnxMT2 and S-adenosyl-L-methionine into the PnxGT2 reaction mixture afforded natural FD-594 to confirm that the PnxGT2 reaction product was the expected regiospecifically glycosylated compound. Consequently, the identified pnx gene cluster appears to be involved in FD-594 biosynthesis.
3. Asymmetric Total Synthesis of the Complex Polycyclic Xanthone FD-594
Tao Xie, Chaoying Zheng, Kuanwei Chen, Haibing He, Shuanhu Gao Angew Chem Int Ed Engl. 2020 Mar 9;59(11):4360-4364. doi: 10.1002/anie.201915787. Epub 2020 Feb 3.
A highly convergent approach was developed to achieve the first asymmetric and scalable total synthesis of FD-594, a complex polycyclic xanthone natural product from Streptomyces sp. TA-0256, in a longest linear sequence (LLS) of 20 steps. The trans-9,10-dihydrophenanthrene-9,10-diol fragment (B-C-D ring) was generated through a new strategy involving asymmetric dihydroxylation followed by Cu-mediated oxidative cyclization. Late-stage stereoselective glycosylation assembled the angular hexacyclic framework with a β-linked 2,6-dideoxy trisaccharide fragment.
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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 ╳
