FR901469
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| Category | Antibiotics |
| Catalog number | BBF-03571 |
| CAS | |
| Molecular Weight | 1533.76 |
| Molecular Formula | C71H116N14O23 |
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Description
FR901469 is an antifungal antibiotic produced by fungal sp. No. 11243. It inhibits the activity of 1, 3-β-glucan synthase, and has strong anti-Candida albicans and Aspergillus fumigatus activity in vitro and in vivo.
Specification
| Synonyms | FR-901469; Lipopeptidolactone FR901469 |
| IUPAC Name | (3R)-3-[(3S,6R,9S,11R,15S,18S,21R,24R,28R,31S,34R,40S,43S,44S)-31-(3-aminopropyl)-11,44-dihydroxy-3,6,24,34-tetrakis[(1R)-1-hydroxyethyl]-18-[(4-hydroxyphenyl)methyl]-21-methyl-2,5,8,14,17,20,23,26,30,33,36,39,42-tridecaoxo-15-propan-2-yl-28-tridecyl-29-oxa-1,4,7,13,16,19,22,25,32,35,38,41-dodecazatricyclo[41.3.0.09,13]hexatetracontan-40-yl]-3-hydroxypropanamide |
| Canonical SMILES | CCCCCCCCCCCCCC1CC(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N2CC(CC2C(=O)NC(C(=O)NC(C(=O)N3CCC(C3C(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)O1)CCCN)C(C)O)C(CC(=O)N)O)O)C(C)O)C(C)O)O)C(C)C)CC4=CC=C(C=C4)O)C)C(C)O |
| InChI | InChI=1S/C71H116N14O23/c1-9-10-11-12-13-14-15-16-17-18-19-21-45-32-52(95)78-55(38(5)86)65(101)75-37(4)61(97)77-47(30-42-23-25-43(90)26-24-42)62(98)80-54(36(2)3)69(105)85-35-44(91)31-48(85)63(99)81-57(40(7)88)67(103)82-58(41(8)89)70(106)84-29-27-49(92)60(84)68(104)83-59(50(93)33-51(73)94)64(100)74-34-53(96)79-56(39(6)87)66(102)76-46(22-20-28-72)71(107)108-45/h23-26,36-41,44-50,54-60,86-93H,9-22,27-35,72H2,1-8H3,(H2,73,94)(H,74,100)(H,75,101)(H,76,102)(H,77,97)(H,78,95)(H,79,96)(H,80,98)(H,81,99)(H,82,103)(H,83,104)/t37-,38-,39-,40-,41-,44-,45-,46+,47+,48+,49+,50-,54+,55-,56-,57-,58+,59+,60+/m1/s1 |
| InChI Key | LTLDDYQPSWDOBJ-UNEDFBIISA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | fungi |
| Melting Point | 182-187°C |
Reference Reading
1. Identification of a putative FR901469 biosynthesis gene cluster in fungal sp. No. 11243 and enhancement of the productivity by overexpressing the transcription factor gene frbF
Makoto Matsui, Tatsuya Yokoyama, Kaoru Nemoto, Toshitaka Kumagai, Goro Terai, Koichi Tamano, Masayuki Machida, Takashi Shibata J Biosci Bioeng. 2017 Feb;123(2):147-153. doi: 10.1016/j.jbiosc.2016.08.007. Epub 2016 Sep 19.
FR901469 is an antifungal antibiotic produced by fungal sp. No. 11243. Here, we searched for FR901469 biosynthesis genes in the genome of No. 11243. Based on the molecular structure of FR901469 and endogenous functional motifs predicted in each genomic NRPS gene, a putative FR901469 biosynthesis gene cluster harboring the most plausible NRPS gene was identified. A transcription factor gene, designated frbF, was found in the cluster. To improve FR901469 productivity, we constructed a strain in which frbF was overexpressed and named it TFH2-2. FR901469 productivity of TFH2-2 was 3.4 times higher than that of the wild-type strain. Transcriptome analysis revealed that most of the genes in the putative FR901469 biosynthesis gene cluster were upregulated in TFH2-2. It also showed that the expression of genes related to ergosterol biosynthesis, β-1,3-glucan catabolism, and chitin synthesis was inclined to exhibit significant differences in TFH2-2.
2. Further enhancement of FR901469 productivity by co-overexpression of cpcA, a cross-pathway control gene, and frbF in fungal sp. No. 11243
Makoto Matsui, Tatsuya Yokoyama, Kaoru Nemoto, Toshitaka Kumagai, Koichi Tamano, Masayuki Machida, Takashi Shibata J Biosci Bioeng. 2017 Jul;124(1):8-14. doi: 10.1016/j.jbiosc.2017.02.015. Epub 2017 Mar 22.
FR901469 is a secondary metabolite with antifungal activity, produced by fungal sp. No. 11243. In our previous study, we constructed the frbF overexpression mutant (TFH2-2) from the wild-type strain. FR901469 productivity of TFH2-2 was 3.4 times higher than that of the wild-type strain. To further enhance FR901469 productivity in TFH2-2, we attempted to find genes from the genome that limited the productivity as bottlenecks in this study. Based on both correlation analysis of gene expression level against FR901469 productivity and genome annotation information, the cross-pathway control gene A (cpcA) was most predicted as the bottleneck. The cpcA and frbF co-overexpression mutant named TFCH3 was then constructed from TFH2-2. As a result, FR901469 productivity of TFCH3 was enhanced at 1.8 times higher than that of TFH2-2. Transcriptome analysis revealed that many genes involved in amino acid biosynthesis and encoding tRNA ligases were significantly upregulated in TFCH3, which implied increase of amino acids as the substrates of FR901469 would be a reason of further productivity enhancement.
3. Genome Sequence of Fungal Species No.11243, Which Produces the Antifungal Antibiotic FR901469
Makoto Matsui, Tatsuya Yokoyama, Kaoru Nemoto, Toshitaka Kumagai, Goro Terai, Masanori Arita, Masayuki Machida, Takashi Shibata Genome Announc. 2015 Apr 2;3(2):e00118-15. doi: 10.1128/genomeA.00118-15.
Fungal species No.11243 was originally isolated from a decayed leaf sample collected in Kyoto, Japan. It produces FR901469, a 1,3-beta-glucan synthase inhibitor. The genome sequence of No.11243 was determined and annotated to obtain useful information for improving productivity of the effective antifungal agent FR901469.
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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 ╳
