Miyakamide A2
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| Category | Antibiotics |
| Catalog number | BBF-01946 |
| CAS | 497252-39-8 |
| Molecular Weight | 508.61 |
| Molecular Formula | C31H32N4O3 |
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Description
Miyakamide A2 is an antibiotic produced by Aspergillus flavus var. columnaris FKI-0739. It has insecticidal effect. Miyakamide A2 inhibits the growth of Artemia salina at a minimum concentration of 5 μg/mL. Miyakamide A1 has weak antixanthomonas activity. It inhibits P388 cells with an IC50 of 12.2 μg/mL.
Specification
| IUPAC Name | (2S)-2-acetamido-N-[(2S)-1-[[(E)-2-(1H-indol-3-yl)ethenyl]amino]-1-oxo-3-phenylpropan-2-yl]-N-methyl-3-phenylpropanamide |
| Canonical SMILES | CC(=O)NC(CC1=CC=CC=C1)C(=O)N(C)C(CC2=CC=CC=C2)C(=O)NC=CC3=CNC4=CC=CC=C43 |
| InChI | InChI=1S/C31H32N4O3/c1-22(36)34-28(19-23-11-5-3-6-12-23)31(38)35(2)29(20-24-13-7-4-8-14-24)30(37)32-18-17-25-21-33-27-16-10-9-15-26(25)27/h3-18,21,28-29,33H,19-20H2,1-2H3,(H,32,37)(H,34,36)/b18-17+/t28-,29-/m0/s1 |
| InChI Key | NNICSBNBJLZHOU-LBBURDNXSA-N |
Properties
| Appearance | Light Yellow Powder |
| Antibiotic Activity Spectrum | Gram-negative bacteria |
| Boiling Point | 860.8±65.0°C at 760 mmHg |
| Melting Point | 98-100°C (dec.) |
| Density | 1.2±0.1 g/cm3 |
Reference Reading
1. New antibiotics miyakamides produced by a fungus
Kazuro Shiomi, Kenji Hatae, Yuichi Yamaguchi, Rokuro Masuma, Hiroshi Tomoda, Susumu Kobayashi, Satoshi Omura J Antibiot (Tokyo). 2002 Nov;55(11):952-61. doi: 10.7164/antibiotics.55.952.
New antibiotics, miyakamides A1, A2, B1, and B2, were isolated from the cultured broth of Aspergillus flavus Link var. columnaris FKI-0739 together with known compounds, parasiticolide A, hydroxyaspergillic acid, and kojic acid. The structure of miyakamide A1 is N-acetyl-L-phenylalanyl-N-methyl-L-phenylalanyl-(alphaZ)-alpha,beta-didehydrotryptamine, and miyakamide A2 is E isomer of A1 at didehydrotryptamine. The structure of miyakamide B1 is N-acetyl-L-tyrosyl-N-methyl-L-phenylalanyl-(alphaZ)-alpha,beta-didehydrotryptamine, and B2 is E isomer of B1. Both miyakamides A1 and B1 existed as equilibrium isomers in solvents, and this isomerism was associated with cis-trans rotation of the amide bond between two amino acids. Conformational isomerism between two amino acids of miyakamides A2 and B2 is cis-form. Miyakamides showed growth inhibitory activity against brine shrimp, Artemia salina.
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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 ╳
