title: Chiral Pyridoxal-Catalyzed Asymmetric Biomimetic Transamination of α-Keto Acids.
abstract: A series of chiral pyridoxals 8 and 9 have been developed from commercially available pyridoxine and (S)-α,α-diarylprolinols. The pyridoxals exhibited good catalytic activity in an asymmetric transamination of α-keto acids with 2,2-diphenylglycine (7f) as the amine source to give various α-amino acids in 29-85% yields with 53-80% ee's. The current asymmetric transamination has successfully mimicked a complete biological transamination process characterized by two half-transaminations, a small chiral pyridoxal molecule acting as the catalyst, and enantioselective control.
authors.affiliation: The Education Ministry Key Lab of Resource Chemistry and Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University , Shanghai 200234, P. R. China.
authors.forename: Limin
authors.initials: L
authors.lastname: Shi
authors.affiliation: The Education Ministry Key Lab of Resource Chemistry and Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University , Shanghai 200234, P. R. China.
authors.forename: Chuangan
authors.initials: C
authors.lastname: Tao
authors.affiliation: The Education Ministry Key Lab of Resource Chemistry and Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University , Shanghai 200234, P. R. China.
authors.forename: Qin
authors.initials: Q
authors.lastname: Yang
authors.affiliation: The Education Ministry Key Lab of Resource Chemistry and Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University , Shanghai 200234, P. R. China.
authors.forename: Yong Ethan
authors.initials: YE
authors.lastname: Liu
authors.affiliation: The Education Ministry Key Lab of Resource Chemistry and Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University , Shanghai 200234, P. R. China.
authors.forename: Jing
authors.initials: J
authors.lastname: Chen
authors.affiliation: The Education Ministry Key Lab of Resource Chemistry and Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University , Shanghai 200234, P. R. China.
authors.forename: Jianfeng
authors.initials: J
authors.lastname: Chen
authors.affiliation: The Education Ministry Key Lab of Resource Chemistry and Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University , Shanghai 200234, P. R. China.
authors.forename: Jiaxin
authors.initials: J
authors.lastname: Tian
authors.affiliation: The Education Ministry Key Lab of Resource Chemistry and Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University , Shanghai 200234, P. R. China.
authors.forename: Feng
authors.initials: F
authors.lastname: Liu
authors.affiliation: The Education Ministry Key Lab of Resource Chemistry and Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University , Shanghai 200234, P. R. China.
authors.forename: Bo
authors.initials: B
authors.lastname: Li
authors.affiliation: The Education Ministry Key Lab of Resource Chemistry and Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University , Shanghai 200234, P. R. China.
authors.forename: Yongling
authors.initials: Y
authors.lastname: Du
authors.affiliation: The Education Ministry Key Lab of Resource Chemistry and Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University , Shanghai 200234, P. R. China.
authors.forename: Baoguo
authors.initials: B
authors.lastname: Zhao
mesh_terms: D000586:Amination; D000596:Amino Acids / Q000737:chemistry; D032701:Biomimetics; D002384:Catalysis; D005998:Glycine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D007651:Keto Acids / Q000737:chemistry*; D015394:Molecular Structure; D011730:Pyridoxal / Q000138:chemical synthesis / Q000737:chemistry*; D011759:Pyrrolidines / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D007651:Keto Acids; D011759:Pyrrolidines; D011730:Pyridoxal; C010509:prolinol; C000606577:2,2-diphenylglycine; D005998:Glycine