Chiral Pyridoxal-Catalyzed Asymmetric Biomimetic Transamination of α-Keto Acids

被引：50

作者：

Shi, Limin

Tao, Chuangan

Yang, Qin

Liu, Yong Ethan

Chen, Jing

Chen, Jianfeng

Tian, Jiaxin

Liu, Feng

Li, Bo

Du, Yongling

Zhao, Baoguo ^{[1
]}

机构：

[1] Shanghai Normal Univ, Educ Minist, Key Lab Resource Chem, Shanghai 200234, Peoples R China

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 23期

关键词：

AMINO-ACIDS; AMINATIVE UMPOLUNG; ENANTIOSELECTIVE SYNTHESIS; OPTICAL INDUCTION; AQUEOUS SYSTEMS; METAL-COMPLEXES; ESTERS; STEREOSELECTIVITY; ISOMERIZATION; ALDEHYDES;

D O I：

10.1021/acs.orglett.5b02895

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of chiral pyridoxals 8 and 9 have been developed from commercially available pyridoxine and (S)-alpha,alpha-diarylprolinols. The pyridoxals exhibited good catalytic activity in an asymmetric transamination of alpha-keto acids with 2,2-diphenylglycine (7f) as the amine source to give various alpha-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.

引用

收藏

页码：5784 / 5787

页数：4

相关论文

共 67 条

[1] A NUCLEAR MAGNETIC RESONANCE INVESTIGATION OF METAL ION AND PROTON-CATALYZED REACTION OF SOME VITAMIN B6 SCHIFF BASES [J].

ABBOTT, EH ;

MARTELL, AE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (25) :6931-&

[2] SYNTHESIS AND REACTION OF A NEW CHIRAL PYRIDOXAMINE ANALOG - SOME DOUBT ABOUT THE STEREOCHEMICAL PROCESS TENTATIVELY PROPOSED FOR A NONENZYMATIC TRANSAMINATION REACTION [J].

ANDO, M ;

KUZUHARA, H .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1989, 62 (01) :244-250

[3] ASYMMETRIC-SYNTHESIS OF FLUOROPHENYLALANINES AND (TRIFLUOROMETHYL)PHENYLALANINES - THE USE OF CHIRAL PYRIDOXAMINE-LIKE PYRIDINOPHANE-ZINC COMPLEX AS AN ENZYME MIMIC [J].

ANDO, M ;

KUZUHARA, H .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (07) :1925-1928

[4] Mimicking enzymatic transaminations:: attempts to understand and develop a catalytic asymmetric approach to chiral α-amino acids [J].

Bachmann, S ;

Knudsen, KR ;

Jorgensen, KA .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (14) :2044-2049

[5] Isotactic polyethylenimines induce formation of L-amino acids in transamination [J].

Bandyopadhyay, Subhajit ;

Zhou, Wenjun ;

Breslow, Ronald .

ORGANIC LETTERS, 2007, 9 (06) :1009-1012

[6] TRANSAMINATION .2. NON-ENZYMIC REACTIONS BETWEEN PYRIDOXAMINE AND PYRUVIC ACID AND BETWEEN PYRIDOXAL AND ALANINE [J].

BANKS, BE ;

DIAMANTIS, AA ;

VERNON, CA .

JOURNAL OF THE CHEMICAL SOCIETY, 1961, (SEP) :4235-&

[7] STEREOSELECTIVITY IN REACTIONS OF METAL-COMPLEXES .7. ASYMMETRIC-SYNTHESIS OF AMINO-ACIDS BY METAL ION-PROMOTED TRANSAMINATION [J].

BERNAUER, K ;

DESCHENAUX, R ;

TAURA, T .

HELVETICA CHIMICA ACTA, 1983, 66 (07) :2049-2058

[8] DEUTERIUM ISOTOPE EFFECTS IN TRANSAMINATION - L-ALANINE AND PYRIDOXAL [J].

BLAKE, MI ;

KATZ, JJ ;

KILPATRICK, M ;

SIEGEL, FP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (03) :294-&

[9] OPTICALLY-ACTIVE AMINO-ACID SYNTHESIS BY ARTIFICIAL TRANSAMINASE ENZYMES [J].

BRESLOW, R ;

CHMIELEWSKI, J ;

FOLEY, D ;

JOHNSON, B ;

KUMABE, N ;

VARNEY, M ;

MEHRA, R .

TETRAHEDRON, 1988, 44 (17) :5515-5524

[10] SELECTIVE TRANSAMINATION AND OPTICAL INDUCTION BY A BETA-CYCLODEXTRIN-PYRIDOXAMINE ARTIFICIAL ENZYME [J].

BRESLOW, R ;

HAMMOND, M ;

LAUER, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (01) :421-422

← 1 2 3 4 5 6 7 →