Orfamide A
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| Category | Bioactive by-products |
| Catalog number | BBF-04281 |
| CAS | 939960-34-6 |
| Molecular Weight | 1295.65 |
| Molecular Formula | C64H114N10O17 |
| Purity | >98% by HPLC |
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Description
It is the major component of a family of cyclic lipopeptides produced by pseudomonas fluorescens pf-5. It is a moderate antifungal agent. It has a profound effect on the swarming motility of bacteria on agar surfaces.
Specification
| Synonyms | N-(3-hydroxy-1-oxotetradecyl)-L-leucyl-D-α-glutamyl-D-allothreonyl-D-alloisoleucyl-L-leucyl-D-seryl-L-leucyl-L-leucyl-D-seryl-L-valine, (10→3)-lactone |
| Storage | Store at -20°C |
| IUPAC Name | (4R)-5-[[(3S,6R,9S,12S,15R,18S,21R,24R,25S)-21-[(2R)-butan-2-yl]-6,15-bis(hydroxymethyl)-25-methyl-9,12,18-tris(2-methylpropyl)-2,5,8,11,14,17,20,23-octaoxo-3-propan-2-yl-1-oxa-4,7,10,13,16,19,22-heptazacyclopentacos-24-yl]amino]-4-[[(2S)-2-(3-hydroxytetradecanoylamino)-4-methylpentanoyl]amino]-5-oxopentanoic acid |
| Canonical SMILES | CCCCCCCCCCCC(CC(=O)NC(CC(C)C)C(=O)NC(CCC(=O)O)C(=O)NC1C(OC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC1=O)C(C)CC)CC(C)C)CO)CC(C)C)CC(C)C)CO)C(C)C)C)O |
| InChI | InChI=1S/C64H114N10O17/c1-15-17-18-19-20-21-22-23-24-25-42(77)32-50(78)65-44(28-35(3)4)56(82)66-43(26-27-51(79)80)55(81)74-54-41(14)91-64(90)52(39(11)12)72-61(87)49(34-76)71-58(84)46(30-37(7)8)67-57(83)45(29-36(5)6)68-60(86)48(33-75)70-59(85)47(31-38(9)10)69-62(88)53(40(13)16-2)73-63(54)89/h35-49,52-54,75-77H,15-34H2,1-14H3,(H,65,78)(H,66,82)(H,67,83)(H,68,86)(H,69,88)(H,70,85)(H,71,84)(H,72,87)(H,73,89)(H,74,81)(H,79,80)/t40-,41+,42?,43-,44+,45+,46+,47+,48-,49-,52+,53-,54-/m1/s1 |
| InChI Key | AFOLBAYDTRBYBA-NZZMYBQCSA-N |
| Source | Pseudomonas fluorescens |
Properties
| Appearance | White Solid |
| Antibiotic Activity Spectrum | Fungi |
| Boiling Point | 1503.0±65.0°C at 760 mmHg |
| Density | 1.2±0.1 g/cm3 |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO; Poorly soluble in Water |
Reference Reading
1. Rhizoxin analogs, orfamide A and chitinase production contribute to the toxicity of Pseudomonas protegens strain Pf-5 to Drosophila melanogaster
Kise L Bond, Marika H Olcott, Joyce E Loper, Baruch Sneh, Virginia O Stockwell, Cedar N Hesse, Barbara J Taylor, Marcella D Henkels, Teresa A Kidarsa, Francesca L Walker, Lorena I Rangel Environ Microbiol . 2016 Oct;18(10):3509-3521. doi: 10.1111/1462-2920.13369.
Pseudomonas protegens strain Pf-5 is a soil bacterium that was first described for its capacity to suppress plant diseases and has since been shown to be lethal to certain insects. Among these is the common fruit fly Drosophila melanogaster, a well-established model organism for studies evaluating the molecular and cellular basis of the immune response to bacterial challenge. Pf-5 produces the insect toxin FitD, but a ΔfitD mutant of Pf-5 retained full toxicity against D. melanogaster in a noninvasive feeding assay, indicating that FitD is not a major determinant of Pf-5's oral toxicity against this insect. Pf-5 also produces a broad spectrum of exoenzymes and natural products with antibiotic activity, whereas a mutant with a deletion in the global regulatory gene gacA produces none of these exoproducts and also lacks toxicity to D. melanogaster. In this study, we made use of a panel of Pf-5 mutants having single or multiple mutations in the biosynthetic gene clusters for seven natural products and two exoenzymes that are produced by the bacterium under the control of gacA. Our results demonstrate that the production of rhizoxin analogs, orfamide A, and chitinase are required for full oral toxicity of Pf-5 against D. melanogaster, with rhizoxins being the primary determinant.
2. A matter of hierarchy: activation of orfamide production by the post-transcriptional Gac-Rsm cascade of Pseudomonas protegens CHA0 through expression upregulation of the two dedicated transcriptional regulators
Claudio Valverde, Julieta Frescura, Andrés Muzlera, Edgardo Jofré, Patricio Martín Sobrero Environ Microbiol Rep . 2017 Oct;9(5):599-611. doi: 10.1111/1758-2229.12566.
In this work, we surveyed the genome of P. protegens CHA0 in order to identify novel mRNAs possibly under the control of the Gac-Rsm cascade that might, for their part, serve to elucidate as-yet-unknown functions involved in the biocontrol of plant pathogens and/or in cellular processes required for fitness in natural environments. In view of the experimental evidence from former studies on the Gac-Rsm cascade, we developed a computational screen supported by a combination of sequence, structural and evolutionary constraints that led to a dataset of 43 potential novel mRNA targets. We then confirmed several mRNA targets experimentally and next focused on two of the respective genes that are physically linked to the orfamide biosynthetic gene cluster and whose predicted open-reading frames resembled cognate LuxR-type transcriptional regulators of cyclic lipopeptide clusters in related pseudomonads. In this report, we demonstrate that in strain CHA0, orfamide production is stringently dependent on a functional Gac-Rsm cascade and that both mRNAs encoding transcriptional regulatory proteins are under direct translational control of the RsmA/E proteins. Our results have thus revealed a hierarchical control over the expression of orfamide biosynthetic genes with the final transcriptional control subordinated to the global Gac-Rsm post-transcriptional regulatory system.
3. Antagonistic bacteria disrupt calcium homeostasis and immobilize algal cells
Maria Mittag, Hannes Dathe, Daniel Schaeme, Christian Hertweck, Prasad Aiyar, María García-Altares, Severin Sasso, David Carrasco Flores Nat Commun . 2017 Nov 24;8(1):1756. doi: 10.1038/s41467-017-01547-8.
Photosynthetic unicellular organisms, known as microalgae, are key contributors to carbon fixation on Earth. Their biotic interactions with other microbes shape aquatic microbial communities and influence the global photosynthetic capacity. So far, limited information is available on molecular factors that govern these interactions. We show that the bacterium Pseudomonas protegens strongly inhibits the growth and alters the morphology of the biflagellated green alga Chlamydomonas reinhardtii. This antagonistic effect is decreased in a bacterial mutant lacking orfamides, demonstrating that these secreted cyclic lipopeptides play an important role in the algal-bacterial interaction. Using an aequorin Ca2+-reporter assay, we show that orfamide A triggers an increase in cytosolic Ca2+in C. reinhardtii and causes deflagellation of algal cells. These effects of orfamide A, which are specific to the algal class of Chlorophyceae and appear to target a Ca2+channel in the plasma membrane, represent a novel biological activity for cyclic lipopeptides.
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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 ╳
