title: Synthesis of octahydropyrano[3,2-b]pyrrole-2-carboxylic acid derivatives from D-mannose.
abstract: Bicyclic amino acids are useful building blocks in synthesizing biologically active molecules and peptidomimetics. 2-Carboxy-6-hydroxyloctahydroindole (Choi) is a novel bicyclic amino acid found in the marine natural products aeruginosins. Many compounds in the aeruginosin family exhibit inhibition activities toward serine proteases including thrombin and trypsin. The unique Choi structure is the common feature of this family of oligopeptides and this motif is important for their observed biological activities. To better understand the influence of the stereochemistry of the Choi core structure on the inhibition activities, we have previously synthesized ring-oxygenated variants from glucose. The preparation of octahydro-pyrano[3,2-b]pyrrole 2-carboxylic acids from d-mannose is reported here. These novel bicyclic amino acids can be used in the preparation of aeruginosin analogs, as well as conformationally constrained peptidomimetics or other biologically active molecules.
authors.affiliation: Department of Chemistry, University of New Orleans, New Orleans, LA 70148, USA.
authors.forename: Jean-Rene
authors.initials: JR
authors.lastname: Ella-Menye
authors.forename: Xiaoping
authors.initials: X
authors.lastname: Nie
authors.forename: Guijun
authors.initials: G
authors.lastname: Wang
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis*; D008358:Mannose / Q000737:chemistry*; D011714:Pyrans / Q000138:chemical synthesis*; D011758:Pyrroles / Q000138:chemical synthesis
chemical_list: D001643:Bridged Bicyclo Compounds; D011714:Pyrans; D011758:Pyrroles; D008358:Mannose