Do the substituent effects affect conformational freedom of squalene in hopene biosynthesis?

Journal of Molecular Modeling

Volumn 17, Issue 9, 2011, Pages 2169-2174

  Nowosielski, Marcin ^a,b   Hoffmann, Marcin ^c  

^a BIOINFOBANK INSTITUTE   (Poland)

^b INSTITUTE OF MEDICAL BIOLOGY   (Poland)

^c ADAM MICKIEWICZ UNIVERSITY   (Poland)

Author keywords

Conformational freedom; Hopene; Lanosterol; Squalene; Substituent effects

Indexed keywords

HOPENE; HYDROGEN; LANOSTEROL DERIVATIVE; LANOSTEROL RING A; METHYL GROUP; SQUALENE; UNCLASSIFIED DRUG;

BIOSYNTHESIS; CALCULATION; CHEMICAL STRUCTURE; CONFERENCE PAPER; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; CYCLIZATION; HYDROGEN BOND; MOLECULAR INTERACTION; NONHUMAN; PRIORITY JOURNAL; SUBSTITUTION REACTION;

COMPUTER SIMULATION; CYCLIZATION; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR CONFORMATION; SQUALENE; THERMODYNAMICS; TRITERPENES;

EID: 80255123888     PISSN: 16102940     EISSN: 09485023     Source Type: Journal    
DOI: 10.1007/s00894-011-1103-7     Document Type: Conference Paper

References (14)

1. RW Hoffmann 2000 Conformation Design of Open-Chain Compounds Angew Chem Int Ed Eng 39 2054 2070 10.1002/1521-3773(20000616)39:12<2054::AID- ANIE2054>3.0.CO;2-Z (Pubitemid 30435588)
2. RW Alder PR Allen KR Anderson CP Butts E Khosravi A Martín CM Maunder AG Orpen ChB St Pourcain 1998 Conformational control by quaternary centres: theory, database evidence and application to polymers J Chem Soc Perkin Trans 2 2083 2107 (Pubitemid 128434916)
3. RW Hoffmann U Schopfer M Stahl 1997 Z- and U-Shaped Open Chain Molecular Backbones by Conformation Design Tetrahedron Lett 38 4055 4058 10.1016/S0040-4039(97)00825-3 1:CAS:528:DyaK2sXktVOru7o%3D (Pubitemid 27232553)
4. KU Wendt GE Schulz EJ Corey DR Liu 2833 (2000) Enzyme Mechanisms for Polycyclic Triterpene Formation Angew Chem Int Edn 39 2812
5. Frisch MJ et al. (2004) Gaussian 03. Gaussian Inc, Wallingford, CT
6. C Møller MS Plesset 1934 Note on an Approximation Treatment for Many-Electron Systems Phys Rev 46 618 622 10.1103/PhysRev.46.618
7. Y Zhao DG Truhlar 2008 Density Functionals with Broad Applicability in Chemistry Acc Chem Res 41 157 167 10.1021/ar700111a 1:CAS:528: DC%2BD1cXksV2iug%3D%3D
8. F Jensen 2002 Polarization Consistent Basis Sets III. The Importance of Diffuse Functions J Chem Phys 117 9234 9240 10.1063/1.1515484 1:CAS:528:DC%2BD38Xos1Snsbs%3D
9. R Thoma T Schulz-Gasch B D'Arcy J Benz J Aebi H Dehmlow M Hennig M Stihle A Ruf 2004 Insight into steroid scaffold formation from the structure of human oxidosqualene cyclase Nature 432 118 122 10.1038/nature02993 1:CAS:528:DC%2BD2cXpt1eit7g%3D (Pubitemid 39490838)
10. T Hoshino T Sato 2002 Squalene-Hopene Cyclase: Catalytic Mechanism and Substrate Recognition Chem Commun (Camb) 4 291 301 10.1039/b108995c (Pubitemid 34177697)
11. MK Leong VS Mastryukov JE Boggs 1994 Structure and Conformations of Six-Membered Systems A6H12 (A;=;C, Si): Ab Initio Study of Cyclohexane and Cyclohexasilane J Phys Chem 98 6961 6966 10.1021/j100079a013 1:CAS:528:DyaK2cXksFKksbc%3D
12. NL Allinger MA Miller 1961 Conformational Analysis. XVII.1 The 1,3-Diaxial Methyl-Methyl Interaction J Am Chem Soc 83 2145 2146 10.1021/ja01470a024 1:CAS:528:DyaF3MXhtFyiurc%3D
13. Nishio M, Hirota M, Umezaw Y (1998) The CH-[pi] interaction: evidence, nature, and consequences. Wiley, New York
14. Y Umezawaa S Tsuboyamab H Takahashib J Uzawab M Nishio 1999 CH/π interaction in the conformation of organic compounds. A database study Tetrahedron 55 10047 10056 10.1016/S0040-4020(99)00539-6 (Pubitemid 29362786)