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Collect. Czech. Chem. Commun. 2004, 69, 261-266
https://doi.org/10.1135/cccc20040261

Formation of Ring A in the Biosynthesis of Hopanoids from Squalene. A Density Functional Study

B. Andes Hess, Jr.

Department of Chemistry, Vanderbilt University, Nashville, TN 37235, U.S.A.

Crossref Cited-by Linking

  • Diao Hongjuan, Chen Nanhao, Wang Kai, Zhang Fan, Wang Yong-Heng, Wu Ruibo: Biosynthetic Mechanism of Lanosterol: A Completed Story. ACS Catal. 2020, 10, 2157. <https://doi.org/10.1021/acscatal.9b05221>
  • Hess B. Andes: Computational studies on the cyclization of squalene to the steroids and hopenes. Org. Biomol. Chem. 2017, 15, 2133. <https://doi.org/10.1039/C7OB00222J>
  • Hess B. Andes, Smentek Lidia, Noel Joseph P., O’Maille Paul E.: Physical Constraints on Sesquiterpene Diversity Arising from Cyclization of the Eudesm-5-yl Carbocation. J. Am. Chem. Soc. 2011, 133, 12632. <https://doi.org/10.1021/ja203342p>
  • Tantillo Dean J.: Biosynthesis via carbocations: Theoretical studies on terpene formation. Nat Prod Rep 2011, 28, 1035. <https://doi.org/10.1039/c1np00006c>
  • Smentek Lidia, Hess B. Andes: Compelling Computational Evidence for the Concerted Cyclization of the ABC Rings of Hopene from Protonated Squalene. J. Am. Chem. Soc. 2010, 132, 17111. <https://doi.org/10.1021/ja1039133>
  • Matsuda Seiichi P. T., Wilson William K., Xiong Quanbo: Mechanistic insights into triterpene synthesis from quantum mechanical calculations. Detection of systematic errors in B3LYP cyclization energies. Org. Biomol. Chem. 2006, 4, 530. <https://doi.org/10.1039/b513599k>
  • Hess B. Andes, Smentek Lidia: Concerted Nature of AB Ring Formation in the Enzymatic Cyclization of Squalene to Hopenes. Org. Lett. 2004, 6, 1717. <https://doi.org/10.1021/ol0496125>
  • Andes Hess B., Smentek Lidia: Density functional study on formation of A and B rings in conversion of 2,3-oxidosqualene to lanosterol. Molecular Physics 2004, 102, 1201. <https://doi.org/10.1080/00268970410001728726>