FD-891
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| Category | Antibiotics |
| Catalog number | BBF-02838 |
| CAS | 142383-53-7 |
| Molecular Weight | 578.77 |
| Molecular Formula | C33H54O8 |
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Description
FD-891 is originally isolated from Streptomyces graminofaciiens A-8890. Its killing activity against human and mouse leukemia cells was 2 to 7 times stronger than that of Doxorubicin, and it also had the activity against Sake yeast.
Specification
| Synonyms | (4Z,6Z,9S,12Z,14Z,16R,17S,18S)-9-[(5S,6R,7R,8S,9S)-5,7-dihydroxy-9-methoxy-6,8-dimethyldecan-2-yl]-2,17-dihydroxy-12,14,16-trimethyl-10,19-dioxabicyclo[16.1.0]nonadeca-4,6,12,14-tetraen-11-one |
| IUPAC Name | (1S,2S,3R,4Z,6Z,10S,12Z,14Z)-10-[(5S,6R,7R,8S,9S)-5,7-dihydroxy-9-methoxy-6,8-dimethyldecan-2-yl]-2,17-dihydroxy-3,5,7-trimethyl-9,19-dioxabicyclo[16.1.0]nonadeca-4,6,12,14-tetraen-8-one |
| Canonical SMILES | CC1C=C(C=C(C(=O)OC(CC=CC=CCC(C2C(C1O)O2)O)C(C)CCC(C(C)C(C(C)C(C)OC)O)O)C)C |
| InChI | InChI=1S/C33H54O8/c1-19-17-21(3)29(36)32-31(41-32)27(35)13-11-9-10-12-14-28(40-33(38)22(4)18-19)20(2)15-16-26(34)24(6)30(37)23(5)25(7)39-8/h9-12,17-18,20-21,23-32,34-37H,13-16H2,1-8H3/b11-9-,12-10-,19-17-,22-18-/t20?,21-,23-,24-,25+,26+,27?,28+,29+,30+,31?,32+/m1/s1 |
| InChI Key | VOLRALTUADVHPT-QOKPVGNQSA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | neoplastics (Tumor); yeast |
| Boiling Point | 749.5°C at 760 mmHg |
| Melting Point | 68.5-72°C |
| Density | 1.071 g/cm3 |
Reference Reading
1. Substrate Recognition by a Dual-Function P450 Monooxygenase GfsF Involved in FD-891 Biosynthesis
Akimasa Miyanaga, Ryuichi Takayanagi, Takashi Furuya, Ayano Kawamata, Tomohiro Itagaki, Yoshiharu Iwabuchi, Naoki Kanoh, Fumitaka Kudo, Tadashi Eguchi Chembiochem. 2017 Nov 2;18(21):2179-2187. doi: 10.1002/cbic.201700429. Epub 2017 Sep 18.
GfsF is a multifunctional P450 monooxygenase that catalyzes epoxidation and subsequent hydroxylation in the biosynthesis of macrolide polyketide FD-891. Here, we describe the biochemical and structural analysis of GfsF. To obtain the structural basis of a dual-function reaction, we determined the crystal structure of ligand-free GfsF, which revealed GfsF to have a predominantly hydrophobic substrate binding pocket. The docking models, in conjunction with the results of the enzymatic assay with substrate analogues and site-directed mutagenesis suggested two distinct substrate binding modes for epoxidation and hydroxylation reactions, which explained how GfsF regulates the order of two oxidative reactions. These findings provide new insights into the reaction mechanism of multifunctional P450 monooxygenases.
2. A concise and unified strategy for synthesis of the C1-C18 macrolactone fragments of FD-891, FD-892 and their analogues: formal total synthesis of FD-891
Naoki Kanoh, Ayano Kawamata, Tomohiro Itagaki, Yuta Miyazaki, Kenzo Yahata, Eunsang Kwon, Yoshiharu Iwabuchi Org Lett. 2014 Oct 3;16(19):5216-9. doi: 10.1021/ol502633j. Epub 2014 Sep 23.
A concise and unified strategy for the synthesis of C1-C18 macrolactone fragments of FD-891 and FD-892 as well as their analogues is reported. The strategy includes a stereoselective vinylogous Mukaiyama aldol reaction (VMAR) using chiral silyl ketene N,O-acetal to construct C6-C7 stereocenters, an E-selective ring closing metathesis to construct a C12-C13 olefin, and stereodivergent construction of a C8-C9 epoxide.
3. Parallel Post-Polyketide Synthase Modification Mechanism Involved in FD-891 Biosynthesis in Streptomyces graminofaciens A-8890
Fumitaka Kudo, Koichi Kawamura, Takashi Furuya, Hiroto Yamanishi, Atsushi Motegi, Akiko Komatsubara, Mario Numakura, Akimasa Miyanaga, Tadashi Eguchi Chembiochem. 2016 Feb 2;17(3):233-8. doi: 10.1002/cbic.201500533. Epub 2016 Jan 8.
To isolate a key polyketide biosynthetic intermediate for the 16-membered macrolide FD-891 (1), we inactivated two biosynthetic genes coding for post-polyketide synthase (PKS) modification enzymes: a methyltransferase (GfsG) and a cytochrome P450 (GfsF). Consequently, FD-892 (2), which lacks the epoxide moiety at C8-C9, the hydroxy group at C10, and the O-methyl group at O-25 of FD-891, was isolated from the gfsF/gfsG double-knockout mutant. In addition, 25-O-methyl-FD-892 (3) and 25-O-demethyl-FD-891 (4) were isolated from the gfsF and gfsG mutants, respectively. We also confirmed that GfsG efficiently catalyzes the methylation of 2 and 4 in vitro. Further, GfsF catalyzed the epoxidation of the double bond at C8-C9 of 2 and 3 and subsequent hydroxylation at C10, to afford 4 and 1, respectively. These results suggest that a parallel post-PKS modification mechanism is involved in FD-891 biosynthesis.
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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 ╳
