AB-0022A

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Category Antibiotics
Catalog number BBF-03183
CAS
Molecular Weight 461.72
Molecular Formula C20H19Cl3O6

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Description

AB-0022A is an antibiotic produced by Dictyostelium purpureum K1001. It has anti-Gram-positive bacteria activity, the MIC against Staphylococcus is 0.39-3.13 μg/mL, and the MIC against Streptococcus and Enterococcus is 25-50 μg/mL.

Specification

Synonyms AB0022A
IUPAC Name 1-(4,6,8-trichloro-1,9-dihydroxy-3,7-dimethoxydibenzofuran-2-yl)hexan-1-one
Canonical SMILES CCCCCC(=O)C1=C(C(=C2C(=C1O)C3=C(C(=C(C(=C3O2)Cl)OC)Cl)O)Cl)OC
InChI InChI=1S/C20H19Cl3O6/c1-4-5-6-7-8(24)9-15(25)10-11-16(26)12(21)20(28-3)14(23)19(11)29-18(10)13(22)17(9)27-2/h25-26H,4-7H2,1-3H3
InChI Key HANVBLRSGDIVGE-UHFFFAOYSA-N

Properties

Appearance Light Yellow Needle Crystal
Antibiotic Activity Spectrum Gram-positive bacteria
Melting Point 144.7-146.1°C

Reference Reading

1. Structure determination and total synthesis of a novel antibacterial substance, AB0022A, produced by a cellular slime mold
T Sawada, M Aono, S Asakawa, A Ito, K Awano J Antibiot (Tokyo). 2000 Sep;53(9):959-66. doi: 10.7164/antibiotics.53.959.
A novel antibacterial substance, AB0022A, was isolated from the cellular slime mold Dictyostelium purpureum K1001. It inhibited the growth of Gram-positive bacteria, and its MICs ranged from 0.39 to 50 microg/ml. Because AB0022A was a highly substituted aromatic compound, we could not determine its structure based on only its physico-chemical and spectral data. We therefore used a dehalogenated derivative from AB0022A and deduced that its structure was 1,9-dihydroxy-3,7-dimethoxy-2-hexanoyl-4,6,8-trichlorodibenzofuran . To confirm this structure, we synthesized the compound having the deduced structure. The synthetic compound was identical to naturally occurring AB0022A.

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