Tetromycin A

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Tetromycin A
Category Antibiotics
Catalog number BBF-04584
CAS 180027-83-2
Molecular Weight 576.76
Molecular Formula C36H48O6
Purity >99% by HPLC

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Description

An unusual tetronic acid, structurally related to kijanimicin, chlorothricin, saccharocarcin, tetrocarcin and versipelostatin. It is an antibiotic produced by Streptomyces. It has pronounced activity against antibiotic susceptible and resistant gram-positive bacteria including MRSA. It appears to target the phosphatidylinositide-3-kinase/akt signalling pathway.

Specification

Synonyms [1S-(1R*,4R*,4aR*,6aS*,7E,11E,12aS*,15S*,16aR*,20aR*,20bS*)]-4-(acetyloxy)-2,3,4,4a,6a,9,10,12a,15,16,20a,20b-dodecahydro-21-hydroxy-1,6,7,11,12a,14,15,20a-octamethyl-18H-16a,19-Metheno-16aH-benzo[b]naphth[2,1-j]oxacyclotetradecin-18,20(1H)-dione; 8-Demethyl-17,32-dideoxy-12,20-dimethyl-kijanolide 9-Acetate
Storage Store at -20°C
IUPAC Name [(1S,3R,6R,7Z,11Z,13R,16S,17S,20S,21R,22S,23Z)-23-hydroxy-3,4,6,8,12,14,20,22-octamethyl-25,27-dioxo-26-oxapentacyclo[22.2.1.01,6.013,22.016,21]heptacosa-4,7,11,14,23-pentaen-17-yl] acetate
Canonical SMILES CC1CCC(C2C1C3(C(C(=CCCC(=CC4(C=C(C(CC45C(=O)C(=C3O)C(=O)O5)C)C)C)C)C)C(=C2)C)C)OC(=O)C
InChI InChI=1S/C36H48O6/c1-19-11-10-12-20(2)29-22(4)15-26-27(41-25(7)37)14-13-21(3)30(26)35(29,9)31(38)28-32(39)36(42-33(28)40)18-24(6)23(5)17-34(36,8)16-19/h12,15-17,21,24,26-27,29-30,38H,10-11,13-14,18H2,1-9H3/b19-16-,20-12-,31-28-/t21-,24+,26+,27-,29+,30+,34+,35+,36+/m0/s1
InChI Key MQEFCZZPPWNMPU-IWMYSMRLSA-N
Source Streptomyces sp.

Properties

Appearance Light Tan Solid
Antibiotic Activity Spectrum Gram-positive bacteria
Boiling Point 684.1±55.0°C at 760 mmHg
Density 1.2±0.1 g/cm3
Solubility Soluble in Ethanol, Methanol, DMF, DMSO; Moderate soluble in Water

Reference Reading

1. New tetromycin derivatives with anti-trypanosomal and protease inhibitory activities
Ute Hentschel, Sheila M Pimentel-Elardo, Verena Buback, Tanja Schirmeister, Tobias A M Gulder, Chris M Ireland, Jason Reppart, Gerhard Bringmann, Tim S Bugni Mar Drugs . 2011;9(10):1682-1697. doi: 10.3390/md9101682.
Four new tetromycin derivatives, tetromycins 1-4 and a previously known one, tetromycin B (5) were isolated from Streptomyces axinellae Pol001(T) cultivated from the Mediterranean sponge Axinella polypoides. Structures were assigned using extensive 1D and 2D NMR spectroscopy as well as HRESIMS analysis. The compounds were tested for antiparasitic activities against Leishmania major and Trypanosoma brucei, and for protease inhibition against several cysteine proteases such as falcipain, rhodesain, cathepsin L, cathepsin B, and viral proteases SARS-CoV M(pro), and PL(pro). The compounds showed antiparasitic activities against T. brucei and time-dependent inhibition of cathepsin L-like proteases with K(i) values in the low micromolar range.

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