title: Chiral polyamines from reduction of polypeptides: asymmetric pyridoxamine-mediated transaminations.
abstract: BH3.THF can reduce polypeptides to polyamines with retention of chirality. The resulting polyamines are intriguing general platforms for asymmetric catalysis, given the diverse structures available and their relative ease of synthesis. We have constructed a number of chiral pyridoxamine catalysts based on reduced peptides. These compounds transaminate alpha-ketoacids with moderate to good enantioselectivity, while their peptidyl counterparts show almost no chiral induction.
authors.affiliation: Department of Chemistry, Columbia University, 3000 Broadway, New York, NY 10027, USA.
authors.forename: Wenjun
authors.initials: W
authors.lastname: Zhou
authors.forename: Nancy
authors.initials: N
authors.lastname: Yerkes
authors.forename: Jason J
authors.initials: JJ
authors.lastname: Chruma
authors.forename: Lei
authors.initials: L
authors.lastname: Liu
authors.forename: Ronald
authors.initials: R
authors.lastname: Breslow
mesh_terms: D001880:Boranes / Q000737:chemistry; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry; D011073:Polyamines / Q000138:chemical synthesis* / Q000737:chemistry; D011733:Pyridoxamine / Q000737:chemistry*; D013237:Stereoisomerism; D013763:Tetrahydrofolates / Q000737:chemistry
chemical_list: D001880:Boranes; D010455:Peptides; D011073:Polyamines; D013763:Tetrahydrofolates; C030371:5,6,7,8-tetrahydrofolic acid; D011733:Pyridoxamine