TAN 420E

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TAN 420E
Category Antibiotics
Catalog number BBF-03876
CAS 91700-93-5
Molecular Weight 576.68
Molecular Formula C30H44N2O9
Purity >95% by HPLC

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Description

Antibiotic TAN 420E is a hydroquinone analogue of herbimycin A with antibacterial, antifungal and antiprotozoan activity.

Specification

Synonyms Dihydro-Herbimycin A; Dihydroherbimycin A
Storage Store at -20°C
IUPAC Name [(4E,6Z,8S,9S,10E,12S,13R,14S,16S,17R)-20,22-dihydroxy-8,13,14,17-tetramethoxy-4,10,12,16-tetramethyl-3-oxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18(22),19-hexaen-9-yl] carbamate
Canonical SMILES CC1CC(C(C(C=C(C(C(C=CC=C(C(=O)NC2=CC(=CC(=C2O)C1OC)O)C)OC)OC(=O)N)C)C)OC)OC
InChI InChI=1S/C30H44N2O9/c1-16-10-9-11-23(37-5)28(41-30(31)36)18(3)12-17(2)27(40-8)24(38-6)13-19(4)26(39-7)21-14-20(33)15-22(25(21)34)32-29(16)35/h9-12,14-15,17,19,23-24,26-28,33-34H,13H2,1-8H3,(H2,31,36)(H,32,35)/b11-9-,16-10+,18-12+/t17-,19-,23-,24-,26+,27+,28-/m0/s1
InChI Key QANBQEQVJJKJTJ-BVXDHVRPSA-N

Properties

Appearance Greenish Tan Lyophilisate
Antibiotic Activity Spectrum fungi
Boiling Point 714.8±60.0°C at 760 mmHg
Density 1.21±0.1 g/cm3

Reference Reading

1. Herbimycins D-F, ansamycin analogues from Streptomyces sp. RM-7-15
Sherif I Elshahawi, Gregory C Copley, Khaled A Shaaban, James C Hower, Andrew J Morris, Xiachang Wang, Larissa V Ponomareva, Jon S Thorson, Madan K Kharel, Manjula Sunkara J Nat Prod . 2013 Sep 27;76(9):1619-26. doi: 10.1021/np400308w.
Bacterial strains belonging to the class actinomycetes were isolated from the soil near a thermal vent of the Ruth Mullins coal fire (Appalachian Mountains of eastern Kentucky). High-resolution electrospray ionization mass spectrometry and ultraviolet absorption profiles of metabolites from one of the isolates (Streptomyces sp. RM-7-15) revealed the presence of a unique set of metabolites ultimately determined to be herbimycins D-F (1-3). In addition, herbimycin A (4), dihydroherbimycin A (TAN 420E) (7), and the structurally distinct antibiotic bicycylomycin were isolated from the crude extract of Streptomyces sp. RM-7-15. Herbimycins A and D-F (1-3) displayed comparable binding affinities to the Hsp90α. While the new analogues were found to be inactive in cancer cell cytotoxicity and antimicrobial assays, they may offer new insights in the context of nontoxic ansamycin-based Hsp90 inhibitors for the treatment of neurodegenerative disease.

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