Paldimycin A
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| Category | Antibiotics |
| Catalog number | BBF-02347 |
| CAS | 101411-70-5 |
| Molecular Weight | 1113.18 |
| Molecular Formula | C44H64N4O23S3 |
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Description
It is produced by the strain of Str. paulus 273. It has anti-gram-positive bacterial effect, but also has weak anti-gram-negative bacterial effect. Paldimycin A has stronger antibacterial activity than Paldimycin B.
Specification
| Synonyms | Antibiotic 273 A1-alpha; L-Cysteine, N-acetyl-, [2-[[2-(acetylamino)-2-carboxyethyl]thio]-1-carboxypropyl]carbamodithioate(ester), 4'-ester with 5-[6-O-acetyl-3-O-[2,6-dideoxy-3-O-methyl-4-C-[1-(2-methyl-1-oxobutoxy)ethyl]-a-L-lyxo-hexopyranosyl]-b-D-allopyranosyl]-2-amino-5-hydroxy-3,6-dioxo-1-cyclohexene-1-carboxylic acid; 2-Amino-5-(3-O-(2,6-dideoxy-4-C-((1S)-1-hydroxyethyl)-3-O-methyl-alpha-L-lyxo-hexopyranosyl)-beta-D-allopyranosyl)-5-hydroxy-3,6-dioxo-1-cyclohexene-1-carboxylic acid, 4'-(3-(((2R)-2-acetamido-2-carboxyethyl)thio)-2-((dithiocarboxy)amino)butyrate), 6'-acetate, 4''-C-((2S)-2-methylbutyrate), S-ester with N-acetyl-L-cysteine |
| IUPAC Name | (3S)-3-[(2R,3R,4S,5R,6R)-5-[(2S,3S)-3-[(2R)-2-acetamido-2-carboxyethyl]sulfanyl-2-[[(2R)-2-acetamido-2-carboxyethyl]sulfanylcarbothioylamino]butanoyl]oxy-6-(acetyloxymethyl)-3-hydroxy-4-[(2S,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyl-5-[(1S)-1-[(2S)-2-methylbutanoyl]oxyethyl]oxan-2-yl]oxyoxan-2-yl]-2,3-dihydroxy-6-imino-5-oxocyclohexene-1-carboxylic acid |
| Canonical SMILES | CCC(C)C(=O)OC(C)C1(C(OC(CC1OC)OC2C(C(OC(C2OC(=O)C(C(C)SCC(C(=O)O)NC(=O)C)NC(=S)SCC(C(=O)O)NC(=O)C)COC(=O)C)C3(CC(=O)C(=N)C(=C3O)C(=O)O)O)O)C)O |
| InChI | InChI=1S/C44H64N4O23S3/c1-10-16(2)40(61)68-19(5)44(64)18(4)67-28(11-27(44)65-9)70-34-32(53)36(43(63)12-25(52)30(45)29(35(43)54)39(59)60)69-26(13-66-22(8)51)33(34)71-41(62)31(17(3)73-14-23(37(55)56)46-20(6)49)48-42(72)74-15-24(38(57)58)47-21(7)50/h16-19,23-24,26-28,31-34,36,45,53-54,63-64H,10-15H2,1-9H3,(H,46,49)(H,47,50)(H,48,72)(H,55,56)(H,57,58)(H,59,60)/t16-,17-,18-,19-,23-,24-,26+,27-,28+,31+,32+,33+,34-,36+,43+,44-/m0/s1 |
| InChI Key | LEXZTVQVBNSLSG-FIQBPEFVSA-N |
Properties
| Appearance | Colorless Acicular Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Density | 1.50 g/cm3 |
| Solubility | Soluble in Chloroform, Methanol, Ethanol |
Reference Reading
1. Paldimycins A and B and antibiotics 273a2 alpha and 273a2 beta. Synthesis and characterization
A D Argoudelis, L Baczynskyj, S A Mizsak, F B Shilliday, P A Spinelli, J DeZwaan J Antibiot (Tokyo). 1987 Apr;40(4):419-36. doi: 10.7164/antibiotics.40.419.
Paldimycin (antibiotic 273a1) and antibiotic 273a2 as well as their individual components, paldimycins A (273a1 alpha) and B (273a1 beta) and antibiotics 273a2 alpha and 273a2 beta were synthesized from paulomycin, paulomycin A and paulomycin B, respectively, by reacting with N-acetyl-L-cysteine. The semisynthetic antibiotics had chromatographic behavior (TLC, HPLC) and physical and chemical properties identical to the properties of the corresponding antibiotics produced by Streptomyces paulus.
2. In vitro activity of paldimycin (U-70138F) against gram-positive bacteria isolated from patients with cancer
K V Rolston, B LeBlanc, D H Ho, G P Bodey Antimicrob Agents Chemother. 1987 Apr;31(4):650-2. doi: 10.1128/AAC.31.4.650.
The in vitro activity of paldimycin, a novel antimicrobial agent, was compared with that of vancomycin against 306 gram-positive isolates (representing 12 bacterial species) obtained from patients with cancer. Paldimycin had lower MICs for 90% of isolates than vancomycin did against most isolates tested. Its activity, however, was medium and pH dependent, being greatest in Nutrient broth at a pH of 6.8.
3. In vitro evaluation of the new paulomycin antibiotic paldimycin
G M Eliopoulos, E Reiszner, R C Moellering Jr Eur J Clin Microbiol. 1987 Jun;6(3):306-8. doi: 10.1007/BF02017620.
The comparative in vitro activity of paldimycin, a new antibiotic, was evaluated against 215 gram-positive bacteria. Activity of the compound was greater in nutrient agar of pH 6.8 than in Mueller-Hinton agar. All strains of staphylococci, streptococci, enterococci and Listeria monocytogenes were inhibited at concentrations less than or equal to 2 micrograms/ml. Activity of the new drug was generally comparable to that of vancomycin.
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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 ╳
