INHIBITORS OF PHENYLALANINE AMMONIA-LYASE - 2-AMINOINDAN-2-PHOSPHONIC ACID AND RELATED-COMPOUNDS

被引：128

作者：

ZON, J

AMRHEIN, N

机构：

[1] Institute of Organic and Physical Chemistry, Technical University Wroclaw, Wroclaw, PL-50-370

[2] Institute of Plant Sciences, Swiss Federal Institut of Technology, Zürich, CH-8092

来源：

LIEBIGS ANNALEN DER CHEMIE | 1992年 / 06期

关键词：

2-AMINOINDAN-2-PHOSPHONIC ACID; ENZYME INHIBITION; PHENYLALANINE AMMONIA-LYASE;

D O I：

10.1002/jlac.1992199201107

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

2-Aminoindan-2-phosphonic acid (3) was synthesized for the first time both directly from 2-indanone (7) as well as by alkylation of ethyl diethoxyphosphorylacetate with 1,2-bis(bromomethyl) benzene (9) via 10 - 12, respectively. 2-Hydroxyindan-2-phosphonic acid (5) was obtained also from 7 via its diisopropyl ester 8. Compound 3 was found to be a potent inhibitor of the plant enzyme phenylalanine ammonia-lyase (EC 4.3.1.5) both in vitro and in vivo. Of the related 2-aminoindan-2-carboxylic acid (4), compound 5, and 1-aminocyclopentylphosphonic acid (6), only 4 inhibited the enzyme but was far less inhibitory than 3.

引用

页码：625 / 628

页数：4

共 25 条

[1] CRYSTALLIZATION AND PROPERTIES OF L-PHENYLALANINE AMMONIA-LYASE FROM RHODOSPORIDIUM-TORULOIDES [J].

ADACHI, O ;

MATSUSHITA, K ;

SHINAGAWA, E ;

AMEYAMA, M .

AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1990, 54 (11) :2839-2843

[2]

AMRHEIN N, 1977, PLANT SCI LETT, V8, P313, DOI 10.1016/0304-4211(77)90148-1

[3]

AMRHEIN N, 1986, RECENT ADV PHYTOCHEM, V20, P83

[4]

BIRYUKOV A, COMMUNICATION

[5] LEUCINE ENKEPHALIN ANALOGS CONTAINING A CONFORMATIONALLY RESTRAINED N-TERMINAL AMINO-ACID RESIDUE [J].

DEEKS, T ;

CROOKS, PA ;

WAIGH, RD .

JOURNAL OF PHARMACEUTICAL SCIENCES, 1984, 73 (04) :457-460

[6]

FLETCHER H, 1970, Patent No. 3532744

[7]

FURATA T, 1990, J AM CHEM SOC, V112, P3633

[8] PHYSIOLOGY AND MOLECULAR-BIOLOGY OF PHENYLPROPANOID METABOLISM [J].

HAHLBROCK, K ;

SCHEEL, D .

ANNUAL REVIEW OF PLANT PHYSIOLOGY AND PLANT MOLECULAR BIOLOGY, 1989, 40 :347-369

[9]

Hanson K. R., 1981, The biochemistry of plants. A comprehensive treatise. Volume 7. Secondary plant products., P577

[10] USE OF N-15 AND DEUTERIUM-ISOTOPE EFFECTS TO DETERMINE THE CHEMICAL MECHANISM OF PHENYLALANINE AMMONIA-LYASE [J].

HERMES, JD ;

WEISS, PM ;

CLELAND, WW .

BIOCHEMISTRY, 1985, 24 (12) :2959-2967

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