Module 3 : Bioorganic Chemistry of Enzymes

Lecture 11 : Biomimetic Polyene Cyclizations

3.14 Selected References
  1. Stryer, L.; Berg, J. M.; Tymoczko, J. L. In Biochemistry, 5th Ed. (Hardcover).
  2. Dugas, H. In Bioorganic Chemistry-A chemical Approach to Enzyme Action, 3rd Edition.
  3. Silverman, R.B. In The organic chemistry of enzyme-catalyzed reactions, Academic Press, San Diego, 2000, 717 pp.
  4. Lehninger Principles of Biochemistry, 5th Ed. by Nelson and Cox.
  5. Sekhon, B. S. Curr. Chem. Biol. 2008, 2, 278-311
  6. Biomimetic Synthesis: (a) Robinson, R. J. Chem. Soc. 1917, 111, 762-768. (b) Willstätter, R. Liebigs Ann. Chem. 1903, 326, 1-42. (c) Langdon, R.G.; Bloch, K. J. Am. Chem. Soc. 1952, 74, 1869-1870. (d) Woodward, R.B.; Bloch, K. J. Am. Chem. Soc. 1953, 75, 2023-2024. (e) Stork, G.; Burgstrahler, A.W. J. Am. Chem. Soc. 1955, 77, 5068. (f) Eschenmoser, A.; Ruzicka, L.; Jeger, O.; Arigoni, D. Helv. Chim. Acta. 1955, 38, 1890-1904. (g) Tchen, T.T.; Bloch, K. J. Biol. Chem. 1957, 226, 931. (h) Eschenmoser, A.; Felix, D.; Gut, M.; Meier, J.; Stadler, P. In Ciba Foundation Symposium on the Biosynthesis of Terpenes and Steroids; Wolstenholme, G.E.W; O’Conner, M., Eds; J. and A. Churchill: London, 1959, pp 217-230. (i) Johnson, W.S.; Crandall, J.K. J. Org. Chem. 1965, 30, 1785-1790.  (j) van Tamelen, E.E. Acc. Chem. Res. 1968, 1, 111-120. (k) van Tamelen, E.E.; Seiler, M.P.; Wierenga, W. J. Am. Chem. Soc. 1972, 94, 8229-8231. (l) Johnson, W.S. Bioorg. Chem. 1976, 5, 51-98. (m) Manitto, P. Biosynthsis of Natural Products; Ellis Harwood: Chichester, 1981; pp 215-313. (n) van Tamelen, E.E.; Hwu, J.R. J. Am. Chem. Soc. 1983,105, 2490-2491. (o) Johnson, W.S. Tetrahedron 1991, 47, xi-1. (p) Heathcock, C.H. Proc. Natl. Acad. Sci., U.S.A. 1996, 93, 14323-14327. (q) Wendt, K.U.; Poralla, K.; Schulz, G.E. Science 1997, 277, 1811-1815. (r) Wendt, K.U.; Schulz, G.E.; Corey, E.J.; Liu, D.R. Angew. Chem. Int. Ed. 2000, 39, 2812-2833. (s) Johnston, J. N. Chem. Rev. 2005, 105, 4730-4756.
  7.  (a) Jencks, W.P. In Catalysis in Chemistry and Enzymology, McGraw-Hill, New York, 1967.
  8. (a) Pollack, S.J.; Jacobs, J.W.; Schultz, P.G. Science 1986, 234, 1570. (b) Tramontano, A.; Janda, K. D.; Lerner, R. A. Science 1986, 234, 1566. (c) Eyring, H.  J. Chem. Phys. 1935, 3, 107. (d) Eyring, H.  Chem. Rev. 1935, 17, 65. (e) Tanaka, F. Chem. Rev. 2002, 102, 4885. (f) Stewart, J. D.; Benkovic, S.J. Nature 1995, 375, 388. (g) Mader, M.M.; Bartlett, P.A.  Chem. Rev. 1997, 97, 1281. (h) Hilvert, D. Annu. Rev. Biochem. 2000, 69, 751–793. (i) Jones, L. H.; Wentworth, P.; Mini Reviews in Medicinal Chemistry 2001, 1, 125–132. (j) Lerner, R. A.; Benkovic, S. J. and Schultz, P. G. Science 1991, 252, 659–667. (k) Xu, Y.; Yamamoto, N.; Janda, K. D. Bioorg. Med. Chem. 2004, 12, 5247 and references therein.