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Angiolam A

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Angiolam A
Category Antibiotics
Catalog number BBF-00468
CAS 99267-41-1
Molecular Weight 587.79
Molecular Formula C34H53NO7

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Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

Fermentation Plant

Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

It is produced by the strain of Angiococcus disciformis An d30. Interfered with protein synthesis and had anti-gram-positive bacterial activity.

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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
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
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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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
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