Saphenamycin
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| Category | Antibiotics |
| Catalog number | BBF-02876 |
| CAS | 634600-55-8 |
| Molecular Weight | 402.40 |
| Molecular Formula | C23H18N2O5 |
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Description
It is a phenazine antibiotic produced by the strain of Str. canarius MG 314-hF8. It has strong effect against gram-positive bacteria and mycobacterium. It inhibits mouse leukemia L5178Y and L1210 cells with ID50 (μg/mL) of 0.15 and 0.6-2.5, respectively (in vitro determination).
Specification
| Related CAS | 83198-27-0 (R-isomer) |
| Synonyms | Antibiotic A-32256; 1-Phenazinecarboxylic acid, 6-(1-((2-hydroxy-6-methylbenzoyl)oxy)ethyl)-; (+/-)-Saphenamycin |
| IUPAC Name | 6-[1-(2-hydroxy-6-methylbenzoyl)oxyethyl]phenazine-1-carboxylic acid |
| Canonical SMILES | CC1=C(C(=CC=C1)O)C(=O)OC(C)C2=C3C(=CC=C2)N=C4C(=N3)C=CC=C4C(=O)O |
| InChI | InChI=1S/C23H18N2O5/c1-12-6-3-11-18(26)19(12)23(29)30-13(2)14-7-4-9-16-20(14)24-17-10-5-8-15(22(27)28)21(17)25-16/h3-11,13,26H,1-2H3,(H,27,28) |
| InChI Key | AXHGAUSFRHOIGV-UHFFFAOYSA-N |
Properties
| Appearance | Yellow Ribbed Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Neoplastics (Tumor); Mycobacteria |
| Boiling Point | 637.6°C at 760 mmHg |
| Melting Point | 200-202°C |
| Density | 1.401 g/cm3 |
| Solubility | Soluble in Methanol, Chloroform |
Reference Reading
1. First synthesis of racemic saphenamycin and its enantiomers. investigation of biological activity
Jane B Laursen, Charlotte G Jørgensen, John Nielsen Bioorg Med Chem. 2003 Mar 6;11(5):723-31. doi: 10.1016/s0968-0896(02)00472-8.
The natural antibiotic saphenamycin, 6-[1-(2-hydroxy-6-methyl-benzoyloxy)-ethyl]-phenazine-1-carboxylic acid, was synthesized from saphenic acid using temporary allyl protection of carboxy and phenoxy functionalities. Resolution of racemic saphenic acid was performed by crystallization of the corresponding (-)-brucine diastereomeric salts and the absolute configuration of (-)-brucinium (-)-saphenate was determined by X-ray crystallography to have R-configuration. This also proved to be the configuration of natural saphenic acid. Enantiomers of saphenamycin were obtained from resolved saphenic acid and screened against a range of skin flora and resistant Staphylococcus aureus strains. Biological activities of saphenamycin enantiomers were compared with that of the synthetic racemate as well as earlier reported activities of saphenamycin isolated from natural sources. No significant difference was observed in activity of the enantiomers of saphenamycin, which revealed that the chirality of saphenamycin has no consequences for the antibiotic activity. Saphenamycin proved to be a potent antibiotic against fusidic acid and rifampicin resistant S. aureus strains showing MIC of 0.1-0.2 microg/mL.
2. Efficient synthesis of glycosylated phenazine natural products and analogs with DISAL (methyl 3,5-dinitrosalicylate) glycosyl donors
Jane B Laursen, Lars Petersen, Knud J Jensen, John Nielsen Org Biomol Chem. 2003 Sep 21;1(18):3147-53. doi: 10.1039/b306789k.
Inspired by the occurrence and function of phenazines in natural products, new glycosylated analogs were designed and synthesized. DISAL (methyl 3,5-dinitrosalicylate) glycosyl donors were used in an efficient and easily-handled glycosylation protocol compatible with combinatorial chemistry. Benzoylated D-glucose, D-galactose and L-quinovose DISAL glycosyl donors were synthesized in high yields and used under mild conditions to glycosylate methyl saphenate and 2-hydroxyphenazine. The glycosides were screened for biological activity and one compound showed inhibitory activity towards topoisomerase II.
3. Insights into a divergent phenazine biosynthetic pathway governed by a plasmid-born esmeraldin gene cluster
Zhe Rui, Min Ye, Shuoguo Wang, Kaori Fujikawa, Bankole Akerele, May Aung, Heinz G Floss, Wenjun Zhang, Tin-Wein Yu Chem Biol. 2012 Sep 21;19(9):1116-25. doi: 10.1016/j.chembiol.2012.07.025.
Phenazine-type metabolites arise from either phenazine-1-carboxylic acid (PCA) or phenazine-1,6-dicarboxylic acid (PDC). Although the biosynthesis of PCA has been studied extensively, PDC assembly remains unclear. Esmeraldins and saphenamycin, the PDC originated products, are antimicrobial and antitumor metabolites isolated from Streptomyces antibioticus Tü 2706. Herein, the esmeraldin biosynthetic gene cluster was identified on a dispensable giant plasmid. Twenty-four putative esm genes were characterized by bioinformatics, mutagenesis, genetic complementation, and functional protein expressions. Unlike enzymes involved in PCA biosynthesis, EsmA1 and EsmA2 together decisively promoted the PDC yield. The resulting PDC underwent a series of conversions to give 6-acetylphenazine-1-carboxylic acid, saphenic acid, and saphenamycin through a unique one-carbon extension by EsmB1-B5, a keto reduction by EsmC, and an esterification by EsmD1-D3, the atypical polyketide sythases, respectively. Two transcriptional regulators, EsmT1 and EsmT2, are required for esmeraldin production.
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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 ╳
