Mureidomycin D
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| Category | Antibiotics |
| Catalog number | BBF-01962 |
| CAS | |
| Molecular Weight | 899.96 |
| Molecular Formula | C40H53N9O13S |
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Description
Mureidomycin D is an antibiotic produced by Str. flavidovirens SANK 60486. It has anti-Pseudomonas aeruginosa activity.
Specification
| IUPAC Name | 2-[[(2S)-1-[[(2R)-3-[[(2S)-2-[(2-aminoacetyl)amino]-3-(3-hydroxyphenyl)propanoyl]-methylamino]-1-[[(E)-[5-(2,4-dioxo-1,3-diazinan-1-yl)-4-hydroxyoxolan-2-ylidene]methyl]amino]-1-oxobutan-2-yl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]carbamoylamino]-3-(3-hydroxyphenyl)propanoic acid |
| Canonical SMILES | CC(C(C(=O)NC=C1CC(C(O1)N2CCC(=O)NC2=O)O)NC(=O)C(CCSC)NC(=O)NC(CC3=CC(=CC=C3)O)C(=O)O)N(C)C(=O)C(CC4=CC(=CC=C4)O)NC(=O)CN |
| InChI | InChI=1S/C40H53N9O13S/c1-21(48(2)36(57)28(43-32(54)19-41)16-22-6-4-8-24(50)14-22)33(35(56)42-20-26-18-30(52)37(62-26)49-12-10-31(53)46-40(49)61)47-34(55)27(11-13-63-3)44-39(60)45-29(38(58)59)17-23-7-5-9-25(51)15-23/h4-9,14-15,20-21,27-30,33,37,50-52H,10-13,16-19,41H2,1-3H3,(H,42,56)(H,43,54)(H,47,55)(H,58,59)(H2,44,45,60)(H,46,53,61)/b26-20+/t21?,27-,28-,29?,30?,33+,37?/m0/s1 |
| InChI Key | HVIYMDRGURCMHG-UBYREJIESA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | Gram-negative bacteria |
| Density | 1.5±0.1 g/cm3 |
Reference Reading
1. Mureidomycins A-D, novel peptidylnucleoside antibiotics with spheroplast forming activity. II. Structural elucidation
F Isono, M Inukai, S Takahashi, T Haneishi, T Kinoshita, H Kuwano J Antibiot (Tokyo). 1989 May;42(5):667-73. doi: 10.7164/antibiotics.42.667.
Structures of new antibiotics, mureidomycins (MRD's) A approximately D, were deduced from spectroscopic analyses and degradation studies. Two residues of m-tyrosine, one residue of 2-amino-3-N-methylaminobutyric acid (AMBA) and methionine are present in all components of the complex. Uracil is contained in MRD's A and C, while dihydrouracil in MRD's B and D. Methionine and m-tyrosine are connected through an ureido bond, and uracil or dihydrouracil is linked to AMBA via enamine sugar moiety. In addition, MRD's C and D contain a glycine residue at the N-terminal.
2. Mureidomycins A-D, novel peptidylnucleoside antibiotics with spheroplast forming activity. III. Biological properties
F Isono, T Katayama, M Inukai, T Haneishi J Antibiot (Tokyo). 1989 May;42(5):674-9. doi: 10.7164/antibiotics.42.674.
Mureidomycins (MRD's) A-D were specifically active against Pseudomonas aeruginosa. Among them, MRD C was most active, with MICs of 0.1 to 3.13 micrograms/ml against many strains of the target organism. Its activity was comparable to that of cefoperazone, ceftazidime and cefsulodin. MRD C-resistant mutants of P. aeruginosa appeared spontaneously at a high frequency when cultured in the presence of the antibiotic. No cross-resistance was observed with beta-lactam antibiotics. A rapid decrease of turbidity along with spheroplast formation and cell lysis was observed when cells of P. aeruginosa were grown in the presence of MRD C. The compounds exhibited low toxicity and protected mice from experimental infection with P. aeruginosa. The urinary and fecal recoveries of MRD C given subcutaneously were 5 and 18%, respectively.
3. Susceptibility of Pseudomonas species to the novel antibiotics mureidomycins
F Isono, K Kodama, M Inukai Antimicrob Agents Chemother. 1992 May;36(5):1024-7. doi: 10.1128/AAC.36.5.1024.
Strains of Pseudomonas aeruginosa, including imipenem- or ofloxacin-resistant clinical isolates, and some other species in the genus Pseudomonas were inhibited by novel antibiotics of the mureidomycin (MRD) group. On the other hand, almost all other gram-positive and gram-negative bacteria were resistant to MRDs, though the antibiotics potently inhibited the in vitro peptidoglycan synthesis of Escherichia coli and P. aeruginosa. All of the strains in the genus Pseudomonas that were inhibited by less than or equal to 200 micrograms of MRDs per ml were classified into the rRNA groups I and III, and none of the tested strains of rRNA group I were resistant to MRDs, suggesting that these two groups are closely related to each other evolutionary. Among group I strains, P. aeruginosa, P. mendocina, P. stutzeri, and P. alcaligenes were more susceptible than the others, suggesting a closer relationship among these species.
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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 ╳
