Angiolam A
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| Category | Antibiotics |
| Catalog number | BBF-00468 |
| CAS | 99267-41-1 |
| Molecular Weight | 587.79 |
| Molecular Formula | C34H53NO7 |
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Description
It is produced by the strain of Angiococcus disciformis An d30. Interfered with protein synthesis and had anti-gram-positive bacterial activity.
Specification
| Synonyms | 1-Oxa-9-azacyclononadec-17-6,8,13,19-tetrone, 15-hydroxy-2-(6-hydroxy-3,7-dimethyl-1,7,9-decatrienyl)-5,10,14,18-pentamethyl-, (2R-(2R*(1E,3S*,6S*,7E),5S*,10R*,14R*,15S*,16S*,17Z))- |
| IUPAC Name | (17E)-15-hydroxy-2-[(1E,7Z)-6-hydroxy-3,7-dimethyldeca-1,7,9-trienyl]-5,10,14,16,18-pentamethyl-1-oxa-9-azacyclononadec-17-ene-6,8,13,19-tetrone |
| Canonical SMILES | CC1CCC(OC(=O)C(=CC(C(C(C(=O)CCC(NC(=O)CC1=O)C)C)O)C)C)C=CC(C)CCC(C(=CC=C)C)O |
| InChI | InChI=1S/C34H53NO7/c1-9-10-22(3)29(36)17-12-21(2)11-15-28-16-13-23(4)31(38)20-32(39)35-26(7)14-18-30(37)27(8)33(40)24(5)19-25(6)34(41)42-28/h9-11,15,19,21,23-24,26-29,33,36,40H,1,12-14,16-18,20H2,2-8H3,(H,35,39)/b15-11+,22-10-,25-19+ |
| InChI Key | GRCRWFPQJFBHLG-ZXXIUXGKSA-N |
Properties
| Appearance | Colorless Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 792.9 °C at 760 mmHg |
| Melting Point | 178-180 °C |
| Density | 1.032 g/cm3 |
Reference Reading
1. Synthesis of angiolam A
Marc Timo Gieseler, Markus Kalesse Org Lett. 2014 Jan 17;16(2):548-51. doi: 10.1021/ol403423r. Epub 2013 Dec 16.
The first total synthesis of angiolam A has been accomplished in 18 steps. Key steps include vinylogous Mukaiyama aldol reactions of aldehyde-derived dienol ethers, conjugate reduction of the resulting double bond followed by diastereoselective protonation and the Witzeman protocol for macrolactamization. Comparison of the optical rotation of the synthesized material with the isolation data established that the absolute configuration of angiolam A is opposite from the proposed structure.
2. Production, isolation, physico-chemical and biological properties of angiolam A, a new antibiotic from Angiococcus disciformis (Myxobacterales)
B Kunze, W Kohl, G Höfle, H Reichenbach J Antibiot (Tokyo). 1985 Dec;38(12):1649-54. doi: 10.7164/antibiotics.38.1649.
Angiolam A, a new lactone-lactam antibiotic, was isolated from the culture broth of the myxobacterium Angiococcus disciformis strain An d30. It was active against a few Gram-positive bacteria and mutant strains of Escherichia coli with increased permeability. It appears to interfere with protein synthesis.
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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 ╳
