Assignment of absolute configuration of the α,β-unsaturated γ-methyl-γ-lactone of the Annonaceous acetogenins by a simple enzymatic method

Tetrahedron Letters

Volumn 37, Issue 39, 1996, Pages 7043-7046

  Duret, P ^a   Waechter, A I ^a   Figadere B ^a   Hocquemiller, R ^a   Cave A ^a   Pierard C ^b   Peres M ^b  

^a CNRS   (France)

^b Institut de Medecine Aerospatiale   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOGENIN; BUTENOLIDE; DEACETYLUVARICIN; LACTIC ACID; MOTRILIN; NEOANNONIN; ROLLINIASTATIN; SQUAMOCIN; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG STRUCTURE; ENZYME ASSAY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; REACTION ANALYSIS; TECHNIQUE;

EID: 0030599221     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01592-4     Document Type: Article

References (15)

1. 1. Part 53 in the series "Acetogenins from Annonaceae. For part 52 see : Silva, E.L.M.; Roblot, F.; Laprévote, O.; Sérani, L.; Cavé, A. J. Org. Chem. 1996 submitted.
2. 2. Cavé, A.; Figadère, B.; Laurens, A., and Cortes, D. in Hertz W. ed., Progress in the Chemistry of Organic Natural Products : Acetogenins from Annonaceae, Springer-Verlag Wien New-York 1996.
3. 3. Rupprecht, J.K.; Hui, Y.-H.; McLaughlin, J.L. J. Nat. Prod. 1990, 53, 237-278.
4. 4. Rieser, M.J.; Hui, Y.-H.; Rupprecht, J.K.; Kozlowski, J.F.; Wood, K.V.; McLaughlin, J.L.; Hanson, P.R.; Zhuang, Z.; Hoye, T.R. J. Am. Chem. Soc. 1992, 114, 10203-10213.
5. 5. Ramirez, E.A.; Hoye, T.R. in Atta Ur-Rahman ed., Studies in Natural Products, Elsevier Amsterdam 1995, 251-282.
6. 6. Hoye, T.R.; Hanson, P.R.; Hasenwinkel, L.E.; Ramirez, E.A.; Zhuang, Z. Tetrahedron Lett. 1994, 35, 8529-8532.
7. 7. Jolad, S.D.; Hoffman, H.J.; Cole, J.R.; Barry, C.E.; Bates, R.B.; Linz, G.S.; Konig, W.A. J. Nat. Prod. 1985, 48, 644-645.
8. 8. Sahai, M.; Singh, S.; Singh, M.; Gupta, Y.K.; Akashi, S.; Yuji, R.; Hirayama, K.; Asaki, H.; Araya, H.; Hara, N.; Eguchi, T.; Kakinuma, K.; and Fujimoto, Y. Chem. Pharm. Bull. 1994, 42, 1163-1174.
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10. 10. Gutmann, I.; Wahlefeld, A.W. in Bergmeyer H.U. ed., Methods of Enzymatic Analysis, Verlag Chemie, Academic Press, Inc. 1974, 3, 1464-1495.
11. 2O [57:57:86] v/v/v. The mixture was stirred two hours at 70°C before being filtered and concentrated. Water (0.5-1 ml) was then added to the residue and the solution was extracted with 3×0.5 ml AcOEt. The organic phases were evaporated and the residue was solubilized in (100-500 μl) buffered solution of 0.1 M TRIS/1N HCl pH=9/hydrazine [80:15:5] v/v/v. 20-50 μl of this alkaline solution were separately uncubated in turn with D-or L-LDH (10 μl) and 20-50 μl of 1% aqueous solution of NAD. Enzymatic preparations were incubated during 20 min at 40°C before HPLC analyses.
12. 12. HPLC experiments : Column (Sup-Rs Spherisorb S5ODS2, 4.6 × 250 mm, Prolabo, France); mobile phase : aqueous solution of 0.2M TRIS/0.1N HCl pH=8/0.2M aqueous solution of 0.425 mM EDTA/MeOH [23.75:26.5:44.75:5] v/v/v/v; flow rate : 1 ml/min; specific UV detection of NADH at 340 nm (sensitivity could be increased using fluorimetric detection with 260 and 460 nm as excitation and emission wavelenghts respectively); sample volume injected : 20-50 μl.
13. 13. Perspiration of the hands containing large amounts of L(+)-lactic acid, care must be taken to ensure that any parts that come in contact with the test solutions, e.g. pipette tips, are not touched with the fingers. Blank reactions were determined for the enzymatic preparations and compared with experimental results.
14. 14. Harmange J.-C.; Figadère B.; Hocquemiller R. Tetrahedron : Asymmetry 1991, 2, 347-350.
15. 15. Rodriguez, A.D.; and Ramirez, C. J. Nat. Prod. 1994, 57, 339-347.