ASELACINS, NOVEL COMPOUNDS THAT INHIBIT BINDING OF ENDOTHELIN TO ITS RECEPTOR .2. ISOLATION AND ELUCIDATION OF STRUCTURES

Citation
Je. Hochlowski et al., ASELACINS, NOVEL COMPOUNDS THAT INHIBIT BINDING OF ENDOTHELIN TO ITS RECEPTOR .2. ISOLATION AND ELUCIDATION OF STRUCTURES, Journal of antibiotics, 47(5), 1994, pp. 528-535
Citations number
5
Categorie Soggetti
Pharmacology & Pharmacy",Immunology
Journal title
ISSN journal
00218820
Volume
47
Issue
5
Year of publication
1994
Pages
528 - 535
Database
ISI
SICI code
0021-8820(1994)47:5<528:ANCTIB>2.0.ZU;2-Y
Abstract
Three novel compounds, named the aselacins, which inhibit the binding of endothelin to its receptor have been isolated from two related Acre monium species of fungi grown in stationary culture. These compounds a re cyclic pentapeptolides with a ring formed by cyclo[Gly-D-Ser-D-Trp- beta-Ala-L-Thr] and an additional exocyclic D-Gln to which is attached a functionalized long chain fatty acid. The aselacins differ in the f unctionalization of this acid. The structures of the aselacins were de termined by amino acid analysis, mass spectrometry and evaluation of 1 -D and 2-D homonuclear and heteronuclear H-1, C-13 and N-15 NMR spectr a in protic and aprotic solvents. The stereochemistry of the amino aci ds present was elucidated by chiral HPLC of hydrolyzed compound.