title: Concise and efficient syntheses of preQ1 base, Q base, and (ent)-Q base.
abstract: To thoroughly study the functional role of prokaryotic t-RNA-guanine-transglycosylases which are essential in the pathogenesis of shigellosis, novel efficient, high-yielding synthetic approaches for preQ(1) base, Q base, as well as for (ent)-Q base mainly employing cheap and readily available starting materials have been developed. Q base as well as (ent)-Q base are accessible starting from preQ(1) base via nucleophilic substitution reactions with appropriately decorated halocyclopentenyl synthons, prior to that prepared from naturally occurring carbohydrates.
authors.affiliation: Institut für Pharmazeutische Chemie der Philipps-Universität Marburg, Marbacher Weg 6, 35032 Marburg, Germany.
authors.forename: Hans-Dieter
authors.initials: HD
authors.lastname: Gerber
authors.forename: Gerhard
authors.initials: G
authors.lastname: Klebe
mesh_terms: D006147:Guanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D011744:Pyrimidinones / Q000138:chemical synthesis* / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C096876:7-(aminomethyl)-7-deazaguanine; D011744:Pyrimidinones; D011758:Pyrroles; D006147:Guanine; C019549:queuine