title: Catalytic Stereoinversion of L-Alanine to Deuterated D-Alanine.
abstract: A combination of an achiral pyridoxal analogue and a chiral base has been developed for catalytic deuteration of L-alanine with inversion of stereochemistry to give deuterated D-alanine under mild conditions (neutral pD and 25 °C) without the use of any protecting groups. This system can also be used for catalytic deuteration of D-alanine with retention of stereochemistry to give deuterated D-alanine. Thus a racemic mixture of alanine can be catalytically deuterated to give an enantiomeric excess of deuterated D-alanine. While catalytic deracemization of alanine is forbidden by the second law of thermodynamics, this system can be used for catalytic deracemization of alanine with deuteration. Such green and biomimetic approach to catalytic stereocontrol provides insights into efficient amino acid transformations.
authors.affiliation: Department of Chemistry, University of Toronto, 80 St George Street, Toronto, ON, M5S 3H6 (Canada) http://www.diaminopharm.com.
authors.forename: Kimia
authors.initials: K
authors.lastname: Moozeh
authors.affiliation: Department of Chemistry, University of Toronto, 80 St George Street, Toronto, ON, M5S 3H6 (Canada) http://www.diaminopharm.com.
authors.forename: Soon Mog
authors.initials: SM
authors.lastname: So
authors.affiliation: Department of Chemistry, University of Toronto, 80 St George Street, Toronto, ON, M5S 3H6 (Canada) http://www.diaminopharm.com. jchin@chem.utoronto.ca.
authors.forename: Jik
authors.initials: J
authors.lastname: Chin
mesh_terms: D000409:Alanine / Q000737:chemistry*; D002384:Catalysis; D002725:Chloroform / Q000737:chemistry; D003903:Deuterium / Q000737:chemistry*; D017666:Deuterium Oxide / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism; D013816:Thermodynamics
chemical_list: D002725:Chloroform; D003903:Deuterium; D017666:Deuterium Oxide; D000409:Alanine
keywords: amino acids; catalysis; deuteration; stereoinversion; stereoselectivity