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Journal of the American Chemical Society

Volumn 129, Issue 31, 2007, Pages 9580-9581

Trapping and structural elucidation of an intermediate in the macrophomate synthase reaction pathway

(4) Serafimov, Jörg M a Westfeld, Thomas a Meier, Beat H a Hilvert, Donald a

a ETH ZURICH (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRONE DERIVATIVE; MACROPHOMATE SYNTHASE; OXALOACETIC ACID; PYRUVIC ACID; SYNTHETASE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; DECARBOXYLATION; DIELS ALDER REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MICHAEL ADDITION; MICHAELIS MENTEN KINETICS; PROTON NUCLEAR MAGNETIC RESONANCE;

CROSS-LINKING REAGENTS; MOLECULAR STRUCTURE; MULTIENZYME COMPLEXES; X-RAY DIFFRACTION;

EID: 34547786838 PISSN: 00027863 EISSN: None Source Type: Journal
DOI: 10.1021/ja073087y Document Type: Article

Times cited : (20)

References (14)

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- Because macrophomate is fluorescent, whereas the starting materials are not, its formation can be monitored by the continuous increase in fluorescence at 420 nm using an excitation wavelength of 310 nm. A significant lag phase is consistently observed for the appearance of product in the total time courses of the MPS-catalyzed reaction, providing additional evidence for the occurrence of a relatively stable intermediate.
- Because macrophomate is fluorescent, whereas the starting materials are not, its formation can be monitored by the continuous increase in fluorescence at 420 nm using an excitation wavelength of 310 nm. A significant lag phase is consistently observed for the appearance of product in the total time courses of the MPS-catalyzed reaction, providing additional evidence for the occurrence of a relatively stable intermediate.

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14
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- It is not possible to deduce the rate at which macrophomate was formed in previous studies (e.g, ref 2) because the published value of k cat (0.6 s-1) was determined at an unspecified enzyme concentration. Nonetheless, based on the increase in fluorescence observed at 420 nm for reactions in 50 mM PIPES, 5 mM MgCl2 (pH 7.0, we estimate the rate constant for the conversion of 5 to 2 to be approximately 1.5 × 10-3 s-1 at 303 K. If we assume 5% conversion for an MPS reaction with 15 mM 1 (10 times K m, then the resulting 0.75 mM 5 would yield macrophomate at an initial rate of (0.75 mM)(1.5 × 10-3 s-1) ≈ 1 μM s-1. If we further assume an MPS concentration of 1 μM, this Vmax would correspond to an apparent k cat of 1 s-1, which is similar in magnitude to the literature va
- -1, which is similar in magnitude to the literature value.

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