Enzymatic synthesis of a ring-contracted analogue of 5- enolpyruvylshikimate-3-phosphate

Organic Letters

Volumn 6, Issue 22, 2004, Pages 4065-4067

  An, Ming ^a,b   Bartlett, Paul A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5 ENOLPYRUVYLSHIKIMATE 3 PHOSPHATE; PHOSPHATE; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; ENZYME SYNTHESIS; MOLECULAR DYNAMICS;

3-PHOSPHOSHIKIMATE 1-CARBOXYVINYLTRANSFERASE; ALKYL AND ARYL TRANSFERASES; CATALYSIS; CYCLOPENTANES; ISOMERISM; MODELS, CHEMICAL; PHOSPHOENOLPYRUVATE; PHOSPHOTRANSFERASES (ALCOHOL GROUP ACCEPTOR); SHIKIMIC ACID;

EID: 8744285741     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048260z     Document Type: Article

References (21)

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14. 2O) δ 0.89.
15. With excess PEP and S3P analogue concentrations of 10-15 mM, the rates of exchange in μmol/h/unit enzyme were approximately 1 (2P), 0.3 (1P), and 0.15 (3P).
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17. 10 made between direct formation of the tetrahedral adduct versus a stepwise process involving a protonated PEP intermediate is subtle, in essence hinging on whether the enzyme provides a negatively charged group capable of stabilizing the cation.
18. (a) Stallings, W. C.; Abdel-Meguid, S. S.; Lim, L. W.; Shieh, H. S.; Dayringer, H. E.; Leimgruber, N. K.; Stegeman, R. A.; Anderson, K. S.; Sikorski, J. A.; Padgette, S. R.; Kishore, G. M. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 5046-5050.
19. (b) Schönbrunn, E.; Eschenburg, S.; Shuttleworth, W. A.; Schloss, J. A.; Amrhein, N.; Evans, J. N.; Kabsch, W. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 1376-1380.
20. We are aware of only two examples in which the nature of the ring itself has been altered. (a) Pawlak, J. L.; Berchtold, G. A. J. Org. Chem. 1988, 53, 4063-4069. The ring-expanded cycloheptadiene 5 was synthesized as an analogue of chorismate; however, 5 is not processed by chorismate mutase, anthranilate synthase, or p-aminobenzoate synthase. (b) Delany, J. J., III; Padykula, R. E.; Berchtold, G. A. J. Am. Chem. Soc. 1992, 114, 1394-1397. In this case, the cyclohexadiene ring of chorismate was replaced with the dihydropyran of 6. Although less reactive than chorismate, the Claisen rearrangement of 6 is accelerated by chorismate mutase by almost the same factor as the natural substrate.
21. We are aware of only two examples in which the nature of the ring itself has been altered. (a) Pawlak, J. L.; Berchtold, G. A. J. Org. Chem. 1988, 53, 4063-4069. The ring-expanded cycloheptadiene 5 was synthesized as an analogue of chorismate; however, 5 is not processed by chorismate mutase, anthranilate synthase, or p-aminobenzoate synthase. (b) Delany, J. J., III; Padykula, R. E.; Berchtold, G. A. J. Am. Chem. Soc. 1992, 114, 1394-1397. In this case, the cyclohexadiene ring of chorismate was replaced with the dihydropyran of 6. Although less reactive than chorismate, the Claisen rearrangement of 6 is accelerated by chorismate mutase by almost the same factor as the natural substrate.