Chaetiacandin
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| Category | Antibiotics |
| Catalog number | BBF-00524 |
| CAS | 96989-32-1 |
| Molecular Weight | 832.92 |
| Molecular Formula | C43H60O16 |
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Description
It is produced by the strain of Monochaetia dimorphospora(Papulacadin). The activity of Chaetiacandin against Candida albicans was stronger than amphotericin B and 5-FC.
Specification
| Synonyms | LS-71333; D-Glucitol, 1,5-Anhydro-1-C-(2,4-Dihydroxy-6-(Hydroxymethyl)Phenyl)-4-O-(6-O-(1-Oxo-2,4-Decadienyl)-Beta-D-Galactopyranosyl)-, 3-(7-Hydroxy-2,4,8,10-Tetradecatetraenoate) |
| IUPAC Name | [5-[5-[2-[(2E,4E)-deca-2,4-dienoyl]oxy-1-hydroxyethyl]-3,4-dihydroxyoxolan-2-yl]oxy-2-[2,4-dihydroxy-6-(hydroxymethyl)phenyl]-3-hydroxy-6-(hydroxymethyl)oxan-4-yl] (2E,4E,8E,10E)-7-hydroxy-12-methyltrideca-2,4,8,10-tetraenoate |
Properties
| Appearance | Colorless Powder |
| Antibiotic Activity Spectrum | yeast |
| Boiling Point | 1007.6 °C at 760 mmHg |
| Melting Point | 128-132 °C |
| Density | 1.35 g/cm3 |
| Solubility | Soluble in Methanol |
Reference Reading
1. Adiponectin-Secretion-Promoting Cyclic Peptide-Polyketide Hybrids from a Halophyte-Associated Fungus, Colletotrichum gloeosporioides JS0417
Changyeol Lee, Junpyo Gong, Jaekyeong Kim, Hyejin Ko, Seungchan An, Sunghee Bang, Stephen T Deyrup, Minsoo Noh, Sang Hee Shim J Nat Prod. 2022 Mar 25;85(3):501-510. doi: 10.1021/acs.jnatprod.1c01102. Epub 2022 Feb 16.
Three new cyclic peptide-polyketide hybrids (1-3) and two new chaetiacandin-type polyketides (4 and 5) along with nine known compounds were isolated from cultures of a halophyte-associated fungus, Colletotrichum gloeosporioides JS0417. Spectroscopic analysis revealed that 1-3 were cyclic depsipeptides where 3,5,11-trihydroxy-2,6-dimethyldodecanoic acid was linked to two amino acids through amide and ester bonds to form a 12-membered ring. Relative and absolute configurations for the peptides were determined with spectroscopic analysis and chemical reactions. The cyclic depsipeptides 2 and 6 were determined to act as strong adiponectin-secretion-promoting modulators with potential to treat metabolic diseases associated with hypoadiponectinemia. Notably, a known compound, tryptophol, significantly inhibited PGE2 synthesis and also promoted adiponectin secretion, exhibiting a similar biological activity profile to aspirin, but with greater potency. The presence of an isoleucine moiety and non-glycosylation may be important for biological activity of the cyclic peptide-polyketide hybrids, and non-methoxylation of the side chain may influence activity of the indole derivatives.
2. Papulacandins and chaetiacandin: a stereoselective route to their basic skeleton by a palladium-mediated arylation of 4,6-O-benzylidene-3-O-tert- butyldimethylsilyl-l-tributyl-stannyl-D-glucal
E Dubois, J M Beau Carbohydr Res. 1992 Jan;223:157-67. doi: 10.1016/0008-6215(92)80014-r.
Palladium(0)-catalysed coupling of 1,5-anhydro-4,6-O-benzylidene-3-O-tert- butyldimethylsilyl-2-deoxy-1-tributylstannyl-D-arabino-hex-1-eni tol (7) with 3,5-dibenzyloxy-2-bromobenzyl alcohol gave 1,1(2)-anhydro-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-1-( 4,6- dibenzyloxy-2-hydroxymethyl-phenyl)-alpha-D-arabino-hexopyranos e (13). The same reaction buffered by sodium carbonate provided 1,5-anhydro-4,6- O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-1-(4,6-dibenzyloxy+ ++-2- hydroxymethyl-phenyl)-D-arabino-hex-1-enitol (11). Stereoselective oxidative spiroacetalisation of 11 provided 1,1(2)- anhydro-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-(4,6-dibenzyl oxy-2- hydroxymethyl-phenyl)-alpha-D-glucopyranose (15), the basic tricyclic structure of papulacandins. In a model study, 15 was converted in three steps into 1,1(2)-anhydro-1-(4,6-dihydroxy-2-hydroxymethylphenyl)-3-O- octadecanoyl-alpha-D-glucopyranose (24), a structural analogue of papulacandin D. Moreover, stereoselective hydroboration-oxidation of 11 furnished 2-(4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-beta-D- glucopyranosyl)-3,5-dibenzyloxy-1-hydroxymethylbenzene (26), the structural skeleton of the chaetiacandin 3.
3. Reductive aromatization of quinols: synthesis of the C-arylglycoside nucleus of the papulacandins and chaetiacandin
K A Parker, A T Georges Org Lett. 2000 Feb 24;2(4):497-9. doi: 10.1021/ol991346l.
[reaction: see text] Nucleophilic 1,2-addition of lithiated glycal 9b to functionalized quinone 7 provided, after reductive aromatization, C-arylglycoside 11b. Treatment with mCPBA afforded the tricyclic papulacandin framework. Alternatively, hydroboration gave the chaetiacandin nucleus.
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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 ╳
