Pradimicin L
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| Category | Antibiotics |
| Catalog number | BBF-02056 |
| CAS | 142062-87-1 |
| Molecular Weight | 870.80 |
| Molecular Formula | C41H46N2O19 |
| Purity | >98% |
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Description
Pradimicin L is an antibiotic produced by Actinomadura verrucosospora subsp. neohibisca. It has antifungal activity.
Specification
| Storage | Store at -20°C |
| IUPAC Name | D-Alanine, N-((5-((4,6-dideoxy-3-O-beta-D-glucopyranosyl-4-(methylamino)-beta-D-galactopyranosyl)oxy)-5,6,8,13-tetrahydro-1,6,9,14-tetrahydroxy-11-methoxy-3-methyl-8,13-dioxobenzo(a)naphthacen-2-yl)carbonyl)-, (5S-trans)- |
Properties
| Appearance | Dark Red Powder |
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 1164.5±75.0°C at 760 mmHg |
| Melting Point | >200°C (dec.) |
| Density | 1.8±0.1 g/cm3 |
| Solubility | Soluble in DMSO |
Reference Reading
1. Pradimicin S, a new pradimicin analog. III. Application of the frit-FAB LC/MS technique to the elucidation of the pradimicin S biosynthetic pathway
K Saitoh, T Furumai, T Oki, F Nishida, K Harada, M Suzuki J Antibiot (Tokyo). 1995 Feb;48(2):162-8. doi: 10.7164/antibiotics.48.162.
The biosynthetic pathway of pradimicin S (PRM-S) was investigated by using sinefungin and bioconversion experiments with aglycones of pradimicin A (PRM-A) and Actinomadura spinosa AA0851, a PRM-S producer. Addition of sinefungin to the strain inhibited the formation of 11-O-demethyl-7-O-methylpradinone II (11dM-7M-PNII) as also determined to occur with its addition to the PRM-A producer. In feeding PRM-A aglycone and its analogs to the strain early in PRM-S biosynthesis, good identifications of bioconverted products were obtained by frit-FAB LC/MS as follows: 11-O-demethylpradinone II (11dM-PNII), 11dM-7M-PNII, 11-O-demethylpradinone I (11dM-PNI), 11-O-demethylpradimicinone I (11dM-PMNI) and pradimicinone I (PMNI) were converted to PRM-S. Pradimicin B (PRM-B) and pradimicin L (PRM-L) were converted to PRMs-L and -S and PRM-S, respectively. A biosynthetic pathway for PRM-S is proposed.
2. Pradimicin-resistance of yeast is caused by a point mutation of the histidine-containing phosphotransfer protein Ypd1
Fumitaka Hiramoto, Nobuhiko Nomura, Tamotsu Furumai, Yasuhiro Igarashi, Toshikazu Oki J Antibiot (Tokyo). 2003 Dec;56(12):1053-7. doi: 10.7164/antibiotics.56.1053.
Pradimicin is an antifungal antibiotic which induces apoptosis like cell death in the yeast Saccharomyces cerevisiae. Pradimicin-resistant mutants were isolated from the S. cerevisiae and the mutation points were analyzed. A point mutation of YPD1 that led to a substitution of the 74th glycine (Gly74) to cysteine (Cys) was identified in a mutant strain NH1. In S. cerevisiae, Ypd1 transfers a phosphoryl group from the sensor kinase Slnl to the response regulator Sskl which regulates a downstream MAP kinase in response to hyperosmotic stress. Gly74 is located in a three-residue reverse turn domain that connects two alpha-helices, one of which contains a histidine residue which is phosphorylated. In the reverse turn, glycine (relative position +10 to the active-site histidine) is highly conserved in Ypd1 and other histidine-containing phosphotransfer proteins. It was therefore suggested that the substitution of Gly74 to Cys altered the Ypd1 structure, which resulted in the resistance to pradimicin.
3. Pradimicin S, a new pradimicin analog. II. Isolation and structure elucidation
K Saitoh, T Tsuno, M Kakushima, M Hatori, T Furumai, T Oki J Antibiot (Tokyo). 1993 Mar;46(3):406-11. doi: 10.7164/antibiotics.46.406.
Pradimicin S was isolated from the culture filtrate of Actinomadura spinosa AA0851. NMR and MS analyses proved that pradimicin S is the 3'-O-(3''-O-sulfo-beta-D-glucopyranosyl) analog of pradimicin A, a new member of the pradimicin family of antibiotics. Stereochemical assignment was made by correlating pradimicin S with pradimicin L.
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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 ╳
