Calcimycin
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| Category | Antibiotics |
| Catalog number | BBF-00596 |
| CAS | 52665-69-7 |
| Molecular Weight | 523.62 |
| Molecular Formula | C29H37N3O6 |
| Purity | >99% by HPLC |
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Description
Calcimycin is an antibiotic produced by Streptomyces chartreusis. It has weak anti-gram-positive bacteria, negative bacteria and fungi activity. It can form stable complexes with divalent cations and exhibit ionophore effects. It is also used as a fluorescent reagent for detecting the hydrophilicity of proteins and as a coupling agent for oxidative phosphorylation.
Specification
| Synonyms | A-23187 |
| Storage | -20°C |
| IUPAC Name | 5-(methylamino)-2-[[(2S,3R,5R,6S,8R,9R)-3,5,9-trimethyl-2-[(2S)-1-oxo-1-(1H-pyrrol-2-yl)propan-2-yl]-1,7-dioxaspiro[5.5]undecan-8-yl]methyl]-1,3-benzoxazole-4-carboxylic acid |
| Canonical SMILES | CC1CCC2(C(CC(C(O2)C(C)C(=O)C3=CC=CN3)C)C)OC1CC4=NC5=C(O4)C=CC(=C5C(=O)O)NC |
| InChI | InChI=1S/C29H37N3O6/c1-15-10-11-29(17(3)13-16(2)27(38-29)18(4)26(33)20-7-6-12-31-20)37-22(15)14-23-32-25-21(36-23)9-8-19(30-5)24(25)28(34)35/h6-9,12,15-18,22,27,30-31H,10-11,13-14H2,1-5H3,(H,34,35)/t15-,16-,17-,18-,22-,27+,29+/m1/s1 |
| InChI Key | HIYAVKIYRIFSCZ-CYEMHPAKSA-N |
| Source | Streptomyces chartreusis |
Properties
| Appearance | White powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; fungi |
| Boiling Point | 710.325°C at 760 mmHg |
| Melting Point | 181-182°C |
| Density | 1.287 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF or DMSO. Poor water solubility. |
Reference Reading
1. Influence of Amino Acid Feeding on Production of Calcimycin and Analogs in Streptomyces chartreusis
Julia E Bandow, Kirstin I Arend Int J Environ Res Public Health . 2021 Aug 19;18(16):8740. doi: 10.3390/ijerph18168740.
Streptomyces chartreusisNRRL 3882 produces the polyether ionophore calcimycin and a variety of analogs, which originate from the same biosynthetic gene cluster. The role of calcimycin and its analogs for the producer is unknown, but calcimycin has strong antibacterial activity. Feeding experiments were performed in chemically defined medium systematically supplemented with proteinogenic amino acids to analyze their individual effects on calcimycin synthesis. In the culture supernatants, in addition to known calcimycin analogs, eight so far unknown analogs were detected using LC-MS/MS. Under most conditions cezomycin was the compound produced in highest amounts. The highest production of calcimycin was detected upon feeding with glutamine. Supplementation of the medium with glutamic acid resulted in a decrease in calcimycin production, and supplementation of other amino acids such as tryptophan, lysine, and valine resulted in the decrease in the synthesis of calcimycin and of the known intermediates of the biosynthetic pathway. We demonstrated that the production of calcimycin and its analogs is strongly dependent on amino acid supply. Utilization of amino acids as precursors and as nitrogen sources seem to critically influence calcimycin synthesis. Even amino acids not serving as direct precursors resulted in a different product profile regarding the stoichiometry of calcimycin analogs. Only slight changes in cultivation conditions can lead to major changes in the metabolic output, which highlights the hidden potential of biosynthetic gene clusters. We emphasize the need to further study the extent of this potential to understand the ecological role of metabolite diversity originating from single biosynthetic gene clusters.
2. Semisynthesis of A23187 (calcimycin) analogs. II. Introduction of a methyl group on the benzoxazole ring
G Jeminet, G Dauphin, J Guyot, M Prudhomme J Antibiot (Tokyo) . 1984 Jun;37(6):627-34. doi: 10.7164/antibiotics.37.627.
Semisynthesis of two demethylamino A23187 with a methyl group in the 4- or 5-position on the benzene ring were carried out via the cleavage of A23187 oxazole ring and rebuilding of modified benzoxazoles. These compounds were shown to release Ca++ and MG++ from mitochondria and to keep part the antibacterial activity of the natural metabolite.
3. Semi-synthesis of A23187 (calcimycin) analogs. III. Modification of benzoxazole ring substituents, ionophorous properties in an organic phase
G Jeminet, G Dauphin, M Prudhomme J Antibiot (Tokyo) . 1986 Jul;39(7):922-33. doi: 10.7164/antibiotics.39.922.
Ten semi-synthetic analogs of A23187 (calcimycin), with only the benzoxazole ring substituents modified together with the ionophore X14885A were studied with regard to their calcium and magnesium carrier properties through an organic phase (toluene - butanol, 70:30). The results indicate that the carboxylic group and the oxazolic nitrogen, maintained in the ortho position are essential for the ionophorous properties. Further, the introduction of a substituent in place of the NHCH3 group, producing steric hindrance of the carboxylic group leads to a destabilization of the 2:1 associations with cations.
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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 ╳
