2-AMINO-3-(5-PHENYLFURAN-2-YL)PROPIONIC ACIDS AND 5-PHENYLFURAN-2-YLACRYLIC ACIDS ARE NOVEL SUBSTRATES OF PHENYLALANINE AMMONIA-LYASE

被引：23

作者：

Paizs, Csaba ^{[1
]}

Tosa, Monica Ioana ^{[1
]}

Bencze, Laszlo Csaba ^{[1
]}

Brem, Juergen ^{[1
]}

Irimie, Florin Dan ^{[1
]}

Retey, Janos ^{[2
]}

机构：

[1] Univ Babes Bolyai, Dept Biochem & Biochem Engn, RO-400028 Cluj Napoca, Romania

[2] Karlsruhe Inst Technol, Inst Organ Chem, D-76128 Karlsruhe, Germany

来源：

HETEROCYCLES | 2011年 / 82卷 / 02期

关键词：

Biocatalysis; MIO Enzyme; Enantioselectivity; Enzyme Mechanism; Chemical Synthesis; TRANS-CINNAMIC ACID; RHODOTORULA-GLUTINIS; DEHYDROALANINE; MECHANISM; PARSLEY; ANALOGS; ENZYME;

D O I：

10.3987/COM-10-S(E)60

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Both racemic 2-amino-3-(5-phenylfuran-2-yl)propionic acids and 5-phenylfuran-2-ylacrylic acids were synthesized and spectroscopically characterized (UV, EI-MS, H-1-NMR and C-13-NMR). The phenyl group of the 5-phenylfuranyl residue carried no (rac-1a) para-Br (rac-1b) or Cl para or ortho (rac-1c, d) substituents. The novel furanylalanines were used as substrates of recombinant phenylalanine ammonia-lyase (PAL). When 50% of the racemic 5-phenylfuranylalanines were converted into the corresponding acrylates, the D-enantiomers of the substrates could be isolated. The L-enantiomers could be prepared from the substituted acrylates when the PAL reaction was reversed in the presence of 6 M ammonia at pH 10.

引用

页码：1217 / +

页数：13

共 20 条

[1] Overexpression of a designed 2.2 kb gene of eukaryotic phenylalanine ammonia-lyase in Escherichia coli [J].

Baedeker, M ;

Schulz, GE .

FEBS LETTERS, 1999, 457 (01) :57-60

[2]

Bartsch S., 2009, ANGEW CHEM, V121, P3412

[3]

BARTSCH S, 2009, ANGEW CHEM INT EDIT, V48, P3532

[4] Free-energy landscape of enzyme catalysis [J].

Benkovic, Stephen J. ;

Hammes, Gordon G. ;

Hammes-Schiffer, Sharon .

BIOCHEMISTRY, 2008, 47 (11) :3317-3321

[5] EFFECTS OF NITRO-GROUPS ON ACIDITIES AND HOMOLYTIC BOND-DISSOCIATION ENTHALPIES OF THE ACIDIC C-H BONDS IN CARBON ACIDS AND THEIR RADICAL-ANIONS [J].

BORDWELL, FG ;

ZHAO, YY .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (20) :6348-6352

[6] Do enzymes sleep and work? [J].

Engelkamp, H ;

Hatzakis, NS ;

Hofkens, J ;

De Schryver, FC ;

Nolte, RJM ;

Rowan, AE .

CHEMICAL COMMUNICATIONS, 2006, (09) :935-940

[7] BIOTRANSFORMATION OF TRANS-CINNAMIC ACID TO L-PHENYLALANINE - OPTIMIZATION OF REACTION CONDITIONS USING WHOLE YEAST-CELLS [J].

EVANS, CT ;

HANNA, K ;

PAYNE, C ;

CONRAD, D ;

MISAWA, M .

ENZYME AND MICROBIAL TECHNOLOGY, 1987, 9 (07) :417-421

[8] The behavior of substrate analogues and secondary deuterium isotope effects in the phenylalanine ammonia-lyase reaction [J].

Gloge, A ;

Langer, B ;

Poppe, L ;

Retey, J .

ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1998, 359 (01) :1-7

[9] Memorandum from the Chemistry Institute, Universisty of Marburg. The action of aromatic diazo compound on alpha,beta-unsaturated carbobyl bonds) [J].

Meerwein, H ;

Buchner, E ;

van Emster, K .

JOURNAL FUR PRAKTISCHE CHEMIE-LEIPZIG, 1939, 152 (7/10) :237-266

[10] Chemoenzymatic one-pot synthesis of enantiopure L-arylalanines from arylaldehydes [J].

Paizs, C ;

Katona, A ;

Rétey, J .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (05) :1113-1116

← 1 2 →