Canescin A
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| Category | Antibiotics |
| Catalog number | BBF-00209 |
| CAS | 24219-64-5 |
| Molecular Weight | 306.27 |
| Molecular Formula | C15H14O7 |
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Description
Canescin is an antibiotic produced by Pemcillum canescene. It is mainly antifungal and has weak antibacterial activity against gram-positive bacteria such as Staphylococcus aureus.
Specification
| IUPAC Name | 6,8-dihydroxy-7-[(2S,4R)-4-methoxy-5-oxooxolan-2-yl]-3-methylisochromen-1-one |
| Canonical SMILES | CC1=CC2=CC(=C(C(=C2C(=O)O1)O)C3CC(C(=O)O3)OC)O |
| InChI | InChI=1S/C15H14O7/c1-6-3-7-4-8(16)12(13(17)11(7)15(19)21-6)9-5-10(20-2)14(18)22-9/h3-4,9-10,16-17H,5H2,1-2H3/t9-,10+/m0/s1 |
| InChI Key | RIGNEELUCYJHBN-VHSXEESVSA-N |
Properties
| Appearance | Colorless needle Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; fungi |
| Melting Point | 200-202°C |
Reference Reading
1. Decrypting the biochemical function of an essential gene from Streptococcus pneumoniae using ThermoFluor technology
Theodore E Carver, Brian Bordeau, Maxwell D Cummings, et al. J Biol Chem. 2005 Mar 25;280(12):11704-12. doi: 10.1074/jbc.M413278200. Epub 2005 Jan 5.
The protein product of an essential gene of unknown function from Streptococcus pneumoniae was expressed and purified for screening in the ThermoFluor affinity screening assay. This assay can detect ligand binding to proteins of unknown function. The recombinant protein was found to be in a dimeric, native-like folded state and to unfold cooperatively. ThermoFluor was used to screen the protein against a library of 3000 compounds that were specifically selected to provide information about possible biological functions. The results of this screen identified pyridoxal phosphate and pyridoxamine phosphate as equilibrium binding ligands (K(d) approximately 50 pM, K(d) approximately 2.5 microM, respectively), consistent with an enzymatic cofactor function. Several nucleotides and nucleotide sugars were also identified as ligands of this protein. Sequence comparison with two enzymes of known structure but relatively low overall sequence homology established that several key residues directly involved in pyridoxal phosphate binding were strictly conserved. Screening a collection of generic drugs and natural products identified the antifungal compound canescin A as an irreversible covalent modifier of the enzyme. Our investigation of this protein indicates that its probable biological role is that of a nucleoside diphospho-keto-sugar aminotransferase, although the preferred keto-sugar substrate remains unknown. These experiments demonstrate the utility of a generic affinity-based ligand binding technology in decrypting possible biological functions of a protein, an approach that is both independent of and complementary to existing genomic and proteomic technologies.
2. Lowdenic acid: a new antifungal polyketide-derived metabolite from a new fungicolous Verticillium sp
Rihab F Angawi, Dale C Swenson, James B Gloer, Donald T Wicklow J Nat Prod. 2003 Sep;66(9):1259-62. doi: 10.1021/np0301285.
Lowdenic acid (1), a new antifungal metabolite with an unusual structure and a mixed biogenetic origin, has been obtained from nonsporulating cultures of a previously undescribed Verticillium sp. (MYC-406 = NRRL 29280) that was isolated as a colonist of polypore basidiomata. The gross structure of 1 was proposed by analysis of NMR data and confirmed by X-ray diffraction analysis, which enabled assignment of relative stereochemistry. Compound 1 occurs as an equilibrium E/Z mixture. The known antifungal metabolite canescin A (2) was also isolated.
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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 ╳
