Mechanistic studies of HPP epoxidase: Configuration of the substrate governs its enzymatic fate

Angewandte Chemie - International Edition

Volumn 41, Issue 23, 2002, Pages 4529-4532

  Zhao, Zongbao ^a   Liu, Pinghua ^a   Murakami, Kazuo ^a   Kuzuyama, Tomohisa ^b   Seto, Haruo ^c   Liu, Hung wen ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

^b UNIVERSITY OF TOKYO   (Japan)

^c TOKYO UNIVERSITY OF AGRICULTURE   (Japan)

Author keywords

Biosynthesis; Enzymes; Fosfomycin; Radicals; Reaction mechanisms

Indexed keywords

BIOCONVERSION; CATALYSIS; HYDROGEN; IRON; OXIDATION; SUBSTRATES;

ENANTIOMERS;

ENZYMES;

2 HYDROXYPROPYLPHOSPHONIC ACID; 2 HYDROXYPROPYLPHOSPHONIC ACID EPOXIDASE; 2-HYDROXYPROPYLPHOSPHONIC ACID EPOXIDASE; ENZYME; FOSFOMYCIN; HEME; HYDROXYPROPYLPHOSPHONIC ACID EPOXIDASE; IRON; OXIDOREDUCTASE; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMISTRY; CONFORMATION; ENANTIOMER; ENZYME ACTIVITY; ENZYME SPECIFICITY; ENZYME STRUCTURE; ENZYME SUBSTRATE; METABOLISM; OXIDATION; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; FOSFOMYCIN; MOLECULAR CONFORMATION; OXIDATION-REDUCTION; OXIDOREDUCTASES; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 0037011396     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20021202)41:23<4529::AID-ANIE4529>3.0.CO;2-2     Document Type: Article

References (29)

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14. 1H NMR spectroscopy. Reaction rates were estimated based on the integrals of the well-resolved methyl signals associated with substrate and product.
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29. A recent report has shown that the (1S,2S)-epoxypropylphosphonic acid exists as a co-metabolite of fosfomycin ((1R,2S)-epoxypropyl-phosphonic acid, 2) in the culture broth of Streptomyces fradiae. Formation of this 1S epimer has been speculated as a result of racemization of the radical intermediate (such as 4 or its equivalent) generated during turnover catalyzed by HPP epoxidase (B. P. Simov, F. Wuggenig, M. Lämmerhofer, W. Lindner, E. Zarbl, F. Hammerschmidt, Eur. J. Org. Chem, 2002, 1139-1142).