Chiral polyamines from reduction of polypeptides: asymmetric pyridoxamine-mediated transaminations.
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.
Zhou
Wenjun
W
Department of Chemistry, Columbia University, 3000 Broadway, New York, NY 10027, USA.
Yerkes
Nancy
N
Chruma
Jason J
JJ
Liu
Lei
L
Breslow
Ronald
R
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
D001880:Boranes; D010455:Peptides; D011073:Polyamines; D013763:Tetrahydrofolates; C030371:5,6,7,8-tetrahydrofolic acid; D011733:Pyridoxamine