title: Isolation and synthesis of novel farnesyl protein transferase inhibitors, valinoctins A and B, from Streptomyces strain MJ858-NF3.
abstract: Two novel farnesyl protein transferase inhibitors, valinoctins A (1) and B (2), were isolated from the fermentation broth of Streptomyces strain MJ858-NF3. The tentative structures of these compounds were elucidated from NMR and mass spectra as dipeptides consisting of valine and a novel amino acyl moiety. Four possible isomers of valinoctin A were synthesized, and the protected derivative of the appropriate compound was crystallized to give the relative stereochemistry of X-ray analysis. Since the valine residue of valinoctin A was determined to be the L-configuration by a chiral HPLC column, absolute configuration of valinoctin A was determined.
authors.affiliation: Department of Applied Chemistry, Keio University, Kanagawa, Japan.
authors.forename: R
authors.initials: R
authors.lastname: Sekizawa
authors.forename: H
authors.initials: H
authors.lastname: Iinuma
authors.forename: Y
authors.initials: Y
authors.lastname: Muraoka
authors.forename: H
authors.initials: H
authors.lastname: Naganawa
authors.forename: N
authors.initials: N
authors.lastname: Kinoshita
authors.forename: H
authors.initials: H
authors.lastname: Nakamura
authors.forename: M
authors.initials: M
authors.lastname: Hamada
authors.forename: T
authors.initials: T
authors.lastname: Takeuchi
authors.forename: K
authors.initials: K
authors.lastname: Umezawa
mesh_terms: D000818:Animals; D001921:Brain / Q000201:enzymology; D002417:Cattle; D018360:Crystallography, X-Ray; D004151:Dipeptides / Q000302:isolation & purification* / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000302:isolation & purification* / Q000494:pharmacology; D005285:Fermentation; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008968:Molecular Conformation; D010458:Peptidyl Transferases / Q000037:antagonists & inhibitors*; D013302:Streptomyces / Q000378:metabolism*
chemical_list: D004151:Dipeptides; D004791:Enzyme Inhibitors; C102702:valinoctin A; C102703:valinoctin B; D010458:Peptidyl Transferases