Diheteropeptin

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Category Enzyme inhibitors
Catalog number BBF-01396
CAS
Molecular Weight 530.65
Molecular Formula C28H42N4O6

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Description

Diheteropeptin is produced by the strain of Diheterospora chlamydospora Q58044. It has similar activity to T ransforming growth factor-β, and inhibits the ability of Histone Deacet ylase.

Specification

IUPAC Name (3S,9S,12R)-3-benzyl-9-[(6R,7R)-6,7-dihydroxyoctyl]-6,6-dimethyl-1,4,7,10-tetrazabicyclo[10.3.0]pentadecane-2,5,8,11-tetrone
Canonical SMILES CC(C(CCCCCC1C(=O)NC(C(=O)NC(C(=O)N2CCCC2C(=O)N1)CC3=CC=CC=C3)(C)C)O)O
InChI InChI=1S/C28H42N4O6/c1-18(33)23(34)15-9-5-8-13-20-24(35)31-28(2,3)27(38)30-21(17-19-11-6-4-7-12-19)26(37)32-16-10-14-22(32)25(36)29-20/h4,6-7,11-12,18,20-23,33-34H,5,8-10,13-17H2,1-3H3,(H,29,36)(H,30,38)(H,31,35)/t18-,20+,21+,22-,23-/m1/s1
InChI Key NAOMMKDKLCMCHA-YDXQKAQTSA-N

Properties

Appearance White Powder
Antibiotic Activity Spectrum neoplastics (Tumor)
Melting Point 74-76°C

Reference Reading

1. Diheteropeptin, a novel substance with TGF-beta-like activity, produced by a fungus, Diheterospora chlamydosporia. II. Physico-chemical properties and structure elucidation
Y Masuoka, K Shin-Ya, K Furihata, H Matsumoto, Y Takebayashi, K Nagai, K Suzuki, Y Hayakawa, H Seto J Antibiot (Tokyo). 2000 Aug;53(8):793-8. doi: 10.7164/antibiotics.53.793.
The structure of diheteropeptin (1), a TGF-beta-like active substance from Diheterospora chlamydosporia Q58044, was determined to be a new cyclotetrapeptide, cyclo[2aminoisobutyryl-(S)-phenylalanyl-(R)-prolyl-(2S,8R,9R)-2-am ino-8,9-dihydroxydecanoyl-] by NMR, mass spectrometric and chemical studies.
2. Diheteropeptin, a new substance with TGF-beta-like activity, produced by a fungus, Diheterospora chlamydosporia. I. Production, isolation and biological activities
Y Masuoka, K Shin-Ya, Y B Kim, M Yoshida, K Nagai, K Suzuki, Y Hayakawa, H Seto J Antibiot (Tokyo). 2000 Aug;53(8):788-92. doi: 10.7164/antibiotics.53.788.
A new metabolite, diheteropeptin, was found in the culture broth of Diheterospora chlamydosporia Q58044 by screening for TGF-beta-like active substances. Diheteropeptin was extracted from the culture supernatant and purified by a series of chromatographies such as silica gel, gel filtration and HPLC. Diheteropeptin exhibited cytostatic activity in Mv1Lu cells with an IC50 value of 20.3 microM and inhibited histone deacetylase.

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