Derailing Dehydroquinate Synthase by Introducing a Stabilizing Stereoelectronic Effect in a Reaction Intermediate

Journal of Organic Chemistry

Volumn 62, Issue 24, 1997, Pages 8582-8585

  Parker, Emily J ^a   Coggins, John R ^b   Abell, Chris ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b UNIVERSITY OF GLASGOW   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000239859     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9713060     Document Type: Article

References (17)

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11. 19F NMR spectra of 10, 13, and 14 are available as Supporting Information.
12. Dehydroquinate synthase was purified according to the method of: Frost, J. W.; Bender, J. L.; Kadonaga, J. T.; Knowles, J. R. Biochemistry 1984, 23, 4470-4475.
13. max values were in the order 1 > 11 < 8. Le Marechal, P.; Froussios, C.; Azerad, R. Biochimie 1986, 68, 1211-1215.
14. It is considered unlikely that the formation of the 14 is due to dehydroquinate synthase using the C-1 epimer of the (6S)-6-fluoroDAHP as a substrate. Less than 4% of this compound is present in the starting material (see Figure 1).
15. Analogous to the increase in stability seen when a fluorine is introduced next to the anomeric center in 2-deoxy-2-fluorosugars. Street, I. P.; Rupitz, K.; Withers, S. G. Biochemistry 1989, 28, 1581-1587.
16. Widlanski, T. S.; Bender, S. L.; Knowles, J. R. J. Am. Chem. Soc. 1987, 109, 1873-1875.
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