FD-892
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-02839 |
| CAS | 145177-62-4 |
| Molecular Weight | 532.75 |
| Molecular Formula | C32H52O6 |
Online Inquiry
Description
It is originally isolated from FD-892. FD-892 has anti-tumor and anti-sake yeast activity, but the activity is weak.
Specification
| Synonyms | (3E,5E,7R,8S,9E,13E,15E,18S)-8-Hydroxy-3,5,7-trimethyl-18-[(2S)-5,7,9-trihydroxy-6,8-dimethyl-2-decanyl]oxacyclooctadeca-3,5,9,13,15-pentaen-2-one |
| IUPAC Name | (3Z,5Z,9Z,13Z,15Z)-8-hydroxy-3,5,7-trimethyl-18-(5,7,9-trihydroxy-6,8-dimethyldecan-2-yl)-1-oxacyclooctadeca-3,5,9,13,15-pentaen-2-one |
| Canonical SMILES | CC1C=C(C=C(C(=O)OC(CC=CC=CCCC=CC1O)C(C)CCC(C(C)C(C(C)C(C)O)O)O)C)C |
| InChI | InChI=1S/C32H52O6/c1-21-19-23(3)28(34)15-13-11-9-8-10-12-14-16-30(38-32(37)24(4)20-21)22(2)17-18-29(35)26(6)31(36)25(5)27(7)33/h8,10,12-15,19-20,22-23,25-31,33-36H,9,11,16-18H2,1-7H3/b10-8-,14-12-,15-13-,21-19-,24-20- |
| InChI Key | BLYZUBYBBZIPIQ-YVKZEFLYSA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | neoplastics (Tumor); yeast |
| Boiling Point | 720.2±60.0°C at 760 mmHg |
| Melting Point | 55-62°C |
| Density | 1.0±0.1 g/cm3 |
Reference Reading
1. Cloning and characterization of the biosynthetic gene cluster of 16-membered macrolide antibiotic FD-891: involvement of a dual functional cytochrome P450 monooxygenase catalyzing epoxidation and hydroxylation
Fumitaka Kudo, Atsushi Motegi, Kazutoshi Mizoue, Tadashi Eguchi Chembiochem. 2010 Jul 26;11(11):1574-82. doi: 10.1002/cbic.201000214.
FD-891 is a 16-membered cytotoxic antibiotic macrolide that is especially active against human leukemia such as HL-60 and Jurkat cells. We identified the FD-891 biosynthetic (gfs) gene cluster from the producer Streptomyces graminofaciens A-8890 by using typical modular type I polyketide synthase (PKS) genes as probes. The gfs gene cluster contained five typical modular type I PKS genes (gfsA, B, C, D, and E), a cytochrome P450 gene (gfsF), a methyltransferase gene (gfsG), and a regulator gene (gfsR). The gene organization of PKSs agreed well with the basic polyketide skeleton of FD-891 including the oxidation states and alpha-alkyl substituent determined by the substrate specificities of the acyltransferase (AT) domains. To clarify the involvement of the gfs genes in the FD-891 biosynthesis, the P450 gfsF gene was inactivated; this resulted in the loss of FD-891 production. Instead, the gfsF gene-disrupted mutant accumulated a novel FD-891 analogue 25-O-methyl-FD-892, which lacked the epoxide and the hydroxyl group of FD-891. Furthermore, the recombinant GfsF enzyme coexpressed with putidaredoxin and putidaredoxin reductase converted 25-O-methyl-FD-892 into FD-891. In the course of the GfsF reaction, 10-deoxy-FD-891 was isolated as an enzymatic reaction intermediate, which was also converted into FD-891 by GfsF. Therefore, it was clearly found that the cytochrome P450 GfsF catalyzes epoxidation and hydroxylation in a stepwise manner in the FD-891 biosynthesis. These results clearly confirmed that the identified gfs genes are responsible for the biosynthesis of FD-891 in S. graminofaciens.
2. 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.
3. 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.
Recommended Products
| BBF-03754 | Castanospermine | Inquiry |
| BBF-02614 | Nystatin | Inquiry |
| BBF-02642 | Lactonamycin | Inquiry |
| BBF-01829 | Deoxynojirimycin | Inquiry |
| BBF-01825 | Loganin | Inquiry |
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
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 ╳
