Schizophrenic behavior of 2,3-oxidosqualene sterol cyclase from pig liver towards 2,3-oxidosqualene analogs

Alain Krief , Romuald Sable , Alain Ronvaux , Willy Dumont , Pat Sandra , Frank David

Chemical Synthesis ›› 2021, Vol. 1 ›› Issue (1) : 6

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Chemical Synthesis ›› 2021, Vol. 1 ›› Issue (1) :6 DOI: 10.20517/cs.2021.03
Research Article

Schizophrenic behavior of 2,3-oxidosqualene sterol cyclase from pig liver towards 2,3-oxidosqualene analogs

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Abstract

We report the unusual behavior of oxidosqualene sterol cyclase from pig liver towards 2,3-oxidosqualene analogs bearing two alkyl groups different from a methyl, at their Δ18-19 double bond: unambiguous structure determinations of the products and tentative rational for their formation are described.

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Biosynthesis / multistep hemi-synthesis of natural product analogs / performance liquid chromatography / structure determination

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Alain Krief, Romuald Sable, Alain Ronvaux, Willy Dumont, Pat Sandra, Frank David. Schizophrenic behavior of 2,3-oxidosqualene sterol cyclase from pig liver towards 2,3-oxidosqualene analogs. Chemical Synthesis, 2021, 1(1): 6 DOI:10.20517/cs.2021.03

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References

[1]

Barrett A,Mies T.Recent developments in polyene cyclizations and their applications in natural product synthesis.Synthesis2018;51:67-82

[2]

Yoder RA.A case study in biomimetic total synthesis: polyolefin carbocyclizations to terpenes and steroids.Chem Rev2005;105:4730-56 PMCID:PMC2575671

[3]

Huff MW.Lord of the rings - the mechanism for oxidosqualene:lanosterol cyclase becomes crystal clear.Trends Pharmacol Sci2005;26:335-40

[4]

Harrison DM.The biosynthesis of triterpenoids and steroids.Nat Prod Rep1985;2:525-60

[5]

Thoma R,D'Arcy B.Insight into steroid scaffold formation from the structure of human oxidosqualene cyclase.Nature2004;432:118-22

[6]

Woodward RB.The cyclization of squalene in cholesterol synthesis.J Am Chem Soc1953;75:2023-4

[7]

Stork G. The stereochemistry of polyene cyclization. Harvard University Organic colloquium Abstract. 1950. Burgstahler AW, PhD. Thesis. Harvard University: 1952.

[8]

Stork G.The stereochemistry of polyene cyclization.J Am Chem Soc1955;77:5068-77

[9]

Eschenmoser A,Jeger O.Zur Kenntnis der Triterpene. 190. Mitteilung. Eine stereochemische Interpretation der biogenetischen Isoprenregel bei den Triterpenen.Helv Chim Acta1955;38:1890-904

[10]

Eschenmoser A.Revisited after 50 years: the “stereochemical interpretation of the biogenetic isoprene rule for the triterpenes”.HCA2005;88:3011-50

[11]

Corey EJ,Ortiz de Montellano PR.2,3-Oxidosqualene, an intermediate in the biological synthesis of sterols from squalene.J Am Chem Soc1966;88:4750-1

[12]

Tamelen EE, Willett JD, Clayton RB, Lord KE. Enzymic conversion of squalene 2,3-oxide to lanosterol and cholesterol.J Am Chem Soc1966;88:4752-4

[13]

Cornforth JW.Olefin alkylation in biosynthesis.Angew Chem Int Ed Engl1968;7:903-11

[14]

Corey EJ,Sarshar S.New mechanistic and stereochemical insights on the biosynthesis of sterols from 2,3-oxidosqualene.J Am Chem Soc1991;113:8171-2

[15]

Wendt KU,Corey EJ.Enzyme mechanisms for polycyclic triterpene formation.Angew. Chem. Int. Edn Engl2000; 39:2812-33

[16]

Hérin M,Krief A.Stereospecific enzymic cyclization of a synthetic 2,3-oxidosqualene analogue bearing an 18Z carbon-carbon double bond.Tetrahedron Letters1979;20:3103-6

[17]

Krief A,Guittet E,Hérin M.Novel results on the biocyclisation of 2,3-oxidosqualene analogs by sterol cyclase.1993;3:365-8

[18]

Krief A,Guittet E,Lallemand JY.About the mechanism of sterol biosynthesis.J Am Chem Soc1987;109:7910-1

[19]

Hogeboom GH.Methods enzymol. Fractionation of cell components of animal tissues. Elsevier; 1955. p. 16-9.

[20]

Tamelen EE, Sharpless KB, Hanzlik R, Clayton RB, Burlingame AL, Wszolek PC. Enzymic cyclization of trans,trans,trans-18,19-dihydrosqualene 2,3-oxide.J Am Chem Soc1967;89:7150-1

[21]

Krief A,Quéré L.Comparison of the behavior of oxidosqualene cyclases from pig liver and yeast toward epoxy-squalene analogues possessing a Δ18-19 Z or E (C, C) double bond.1991;1:365-8

[22]

Krief A,Bahar M,Herrebout W.Elucidation of the absolute configuration of rhizopine by chiral supercritical fluid chromatography and vibrational circular dichroism.J Sep Sci2015;38:2545-50

[23]

Tamelen E, Sharpless KB. Positional selectivity during controlled oxidation of polyolefins.Tetrahedron Letters1967;8:2655-9

[24]

Krief A,Clarembeau M,Badaoui E.Synthesis of α-selenoalkyllithium compounds.Tetrahedron1989;45:2005-22

[25]

Labar D.Connective (C-C) route to hindered epoxides and olefins from hindered ketones.J Chem Soc, Chem Commun1982;10:564-6

[26]

Horner L,Wippel HG.Phosphororganische Verbindungen, XX. Phosphinoxyde als Olefinierungsreagenzien.Chem Ber1959;92:2499-505

[27]

Buss AD.The Wittig-Horner route to tri-substituted alkanes: synthesis of -α-bisabolene.Tetrahedron Letters1983;24:111-4

[28]

Schauder J.Regio and stereochemically controlled ring opening of epoxides with Grignard reagents. Stereocontrolled synthesis of the steroid side chains. first stereoselective hemisynthesis of 20s isolanosterol.Tetrahedron Letters1982;23:4389-92

[29]

Koreeda M.Stereochemically controlled synthesis of 20-isocholesterol.Tetrahedron Letters1978;19:1641-4

[30]

Pasau P. PhD thesis, Facultés Universitaires Notre-Dame de la Paix (FUNDP). Namur; 1992.

[31]

House HO,Olmstead HD.Chemistry of carbanions. XIX. Alkylation of enolates from unsymmetrical ketones.J Org Chem1971;36:2361-71

[32]

Corey EJ.Pyridinium chlorochromate. An efficient reagent for oxidation of primary and secondary alcohols to carbonyl compounds.Tetrahedron Letters1975;16:2647-50

[33]

Evans DA,Grimm KG.Thiosilanes, a promising class of reagents for selective carbonyl protection.J Am Chem Soc1977;99:5009-17

[34]

Barton DHR.A new method for the deoxygenation of secondary alcohols.J Chem Soc, Perkin Trans 11975;

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