title: Synthesis and biological activity of chiral tetrahydrofuranyl amino acids as building moieties of pamamycin analogues.
abstract: A new synthetic route to chiral tetrahydrofuranyl amino acids is described starting with D-glucose. The 17-step and a 20-step procedures, respectively, furnished compounds of the general formulas 1 and 2 mimicking the dimethylamino carboxylic acid part of pamamycin (3). In comparison with the absolute stereochemistry of 3 the acyclic compounds 1a-c and 2a-c are enantiomers. Despite of the presence of a dimethylamino function they showed neither antibacterial activity nor protonophoric effects on an artificial bilayer membrane suggesting that the macrodiolide ring of 3 forms an indispensable prerequisite for the known interaction of this antibiotic with biological systems.
authors.affiliation: Hans-Knöll-Institute for Natural Products Research, Jena, Germany.
authors.forename: E
authors.initials: E
authors.lastname: Krüger-Velthusen
authors.forename: P
authors.initials: P
authors.lastname: Jütten
authors.forename: P A
authors.initials: PA
authors.lastname: Grigoriev
authors.forename: U
authors.initials: U
authors.lastname: Gräfe
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D005663:Furans / Q000138:chemical synthesis* / Q000494:pharmacology*; D018942:Macrolides; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008567:Membranes, Artificial; D008826:Microbial Sensitivity Tests; D009930:Organic Chemicals; D011522:Protons; D013237:Stereoisomerism
chemical_list: D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D005663:Furans; D018942:Macrolides; D008567:Membranes, Artificial; D009930:Organic Chemicals; D011522:Protons; C024500:pamamycin