Resormycin
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| Category | Antibiotics |
| Catalog number | BBF-02181 |
| CAS | |
| Molecular Weight | 486.95 |
| Molecular Formula | C21H31ClN4O7 |
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Description
It is originally isolated from Str. platensis MJ953-SF5. It has a strong herbicide effect, especially on the seeds of dicotyledonous plants. Resormycin also has anti-fungal action, resisting some plant pathogenic fungi, but not resisting bacteria and yeast.
Specification
| IUPAC Name | (Z)-3-(4-chloro-3,5-dihydroxyphenyl)-2-[[(2S)-2-[[(3S)-3,7-diaminoheptanoyl]amino]-3-hydroxy-3-methylbutanoyl]amino]prop-2-enoic acid |
| Canonical SMILES | CC(C)(C(C(=O)NC(=CC1=CC(=C(C(=C1)O)Cl)O)C(=O)O)NC(=O)CC(CCCCN)N)O |
| InChI | InChI=1S/C21H31ClN4O7/c1-21(2,33)18(26-16(29)10-12(24)5-3-4-6-23)19(30)25-13(20(31)32)7-11-8-14(27)17(22)15(28)9-11/h7-9,12,18,27-28,33H,3-6,10,23-24H2,1-2H3,(H,25,30)(H,26,29)(H,31,32)/b13-7-/t12-,18+/m0/s1 |
| InChI Key | LGIARSLOMQCKGX-SMOPJJOVSA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | fungi |
Reference Reading
1. Resormycin, a novel herbicidal and antifungal antibiotic produced by a strain of Streptomyces platensis. II. Structure elucidation of resormycin
M Igarashi, H Nakamura, H Naganawa, T Takeuchi J Antibiot (Tokyo). 1997 Dec;50(12):1026-31. doi: 10.7164/antibiotics.50.1026.
A novel herbicidal antibiotic, resormycin, was isolated from the culture broth of Streptomyces platensis MJ953-SF5. The structure of resormycin is determined to be (2Z)-2-N-[2N-[(3S)-3,6-diaminoheptanoyl]-(2S)-3-hydroxyva lyl]amino-3- (4-chloro-3,5-dihydroxy)phenylpropenoic acid by spectroscopic analyses, degradation studies and X-ray crystallography.
2. Synthesis of Androprostamine A and Resormycin
Hikaru Abe, Yohko Yamazaki, Chiharu Sakashita, Isao Momose, Takumi Watanabe, Masakatsu Shibasaki Chem Pharm Bull (Tokyo). 2016;64(7):982-7. doi: 10.1248/cpb.c16-00207.
Syntheses of androprostamine A (1), and resormycin (3), anti-prostate cancer peptidyl natural products produced by microorganisms, were completed. The characteristic enamide structures of these compounds were installed using the Horner-Wadsworth-Emmons reaction from the corresponding phosphonates in reasonable Z-selectivity.
3. Some biological and biochemical activities of resormycin, a novel herbicidal antibiotic
M Igarashi, M Kawada, M Hamada, H Iinuma, H Hayashi, K Tsuchiya, M Hori J Antibiot (Tokyo). 2001 Dec;54(12):1072-9. doi: 10.7164/antibiotics.54.1072.
Biological and biochemical activities of resormycin were studied using unicellular green algae, Selenastrum capricornutum (abbreviated as Selena.), as a test organism. Resormycin inhibited the growth in vitro of Selena. more strongly in the dark than in the light. A weaker but more photo-stable derivative, (+/-)-2,3-dihydro-resormycin, showed more long-lasting activity against Selena. in the light. Resormycin started killing Selena. only after exposure for 2 days and longer, even at high concentrations. Resormycin at concentrations near IC50 rapidly inhibited incorporation of 3H-leu, but not 3H-UR or 3H-TdR, into the TCA insoluble fraction of Selena. Herbicidal activity of resormycin was confirmed using some crops and weeds.
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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 ╳
