Comparison of the substrate specificity of type I and type II dehydroquinases with 5-deoxy- and 4,5-dideoxy-dehydroquinic acid

Syntheses of 5-deoxydehydroquinic acid and 4,5-dideoxydehydroquinic acid from quinic acid are described. These substrate analogues were tested against the mechanistically-distinct type I and type II dehydroquinases. The C-4 hydroxy group of the substrate is shown to be important for imine formation on the type I enzyme but appears not to contribute significantly to specificity on the type II dehydroquinase.

[1]  T. Krell,et al.  The use of electrospray mass spectrometry to identify an essential arginine residue in type II dehydroquinases , 1995, FEBS letters.

[2]  I. Charles,et al.  Crystallization of a type II dehydroquinase from Mycobacterium tuberculosis. , 1994, Journal of Molecular Biology.

[3]  H. Wickman,et al.  Attachment of a Pseudomonas-like bacterium and Bacillus coagulans to solid surfaces and adsorption of their S-layer proteins , 1993 .

[4]  L. Dijkhuizen,et al.  Purification and characterization of a dual function 3-dehydroquinate dehydratase from Amycolatopsis methanolica. , 1992, Journal of General Microbiology.

[5]  I. Charles,et al.  Inducible overproduction of the Aspergillus nidulans pentafunctional AROM protein and the type-I and -II 3-dehydroquinases from Salmonella typhi and Mycobacterium tuberculosis. , 1992, The Biochemical journal.

[6]  N. C. Price,et al.  A comparison of the enzymological and biophysical properties of two distinct classes of dehydroquinase enzymes. , 1992, The Biochemical journal.

[7]  J. Coggins,et al.  Observation of an imine intermediate on dehydroquinase by electrospray mass spectrometry , 1991 .

[8]  B. Ganem,et al.  Short chemical synthesis of (-)-chorismic acid from (-)-shikimic acid , 1990 .

[9]  J. Coggins,et al.  The purification and characterization of 3-dehydroquinase from Streptomyces coelicolor. , 1990, The Biochemical journal.

[10]  A. Fersht.  Relationships between apparent binding energies measured in site-directed mutagenesis experiments and energetics of binding and catalysis. , 1988, Biochemistry.

[11]  J. Coggins,et al.  Purification and characterization of 3-dehydroquinase from Escherichia coli. , 1986, The Biochemical journal.

[12]  G. A. Berchtold,et al.  (-)-Methyl 4,5-O-benzylidene-4-epi-shikimate: an intermediate for the synthesis of (-)-chorismic acid and analogs , 1985 .

[13]  J. Secrist,et al.  Nucleoside 4',5'-enol acetates. Synthesis and chemistry of a unique uridine O2,4'-anhydronucleoside , 1979 .

[14]  J. G. Moffatt,et al.  Reactions of 2-acyloxyisobutyryl halides with nucleosides. I. Reactions of model diols and of uridine. , 1973, Journal of the American Chemical Society.

[15]  R. Grewe,et al.  Die Synthese der 5-Dehydro-chinasäure , 1956 .