Facile chemo-enzymatic access to monoglucosyl derivatives of 2,3-oxirane dimethanol

Tetrahedron Asymmetry

Volumn 7, Issue 10, 1996, Pages 2773-2774

  Trincone, Antonio ^a   Pagnotta, Edoardo ^a  

^a Ist per la Chim di Molecole di I   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ETHYLENE OXIDE DERIVATIVE; GLUCOSIDE;

ARTICLE; DRUG SYNTHESIS; ENZYME ACTIVITY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030271742     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00358-8     Document Type: Article

References (14)

1. 1. Wong, C.H., Whitesides, G.M. (1994) Enzymes in synthetic organic chemistry. Tetrahedron Organic Chemistry Series. J.E. Baldwin and P.D. Magnus, eds Elsevier Science Ltd., Oxford UK.
2. 2. (a) Trincone, A., Improta, R., Gambacorta, A. Biocatalysis and Biotransformation 1995 12, 77-88
3. (b) Trincone, A., Nicolaus, B., Lama, L., Gambacorta, A. J. Chem. Soc Perkin Trans I , 1991 2841-2844
4. (c) Trincone, A., Pagnotta, E., Sodano, G. Tetrahedron Letters 1994 35, 1415-1416
5. 3. Soriente, A., De Rosa, M., Trincone A., Sodano, G. Bioorganic and Medicinal Chemistry Letters 1995 5, 20, 2321-2324
6. 4. Almond -β-glucosidase (5.7 U/mg) was obtained from Sigma. Crude homogenates of the thermophilic microorganisms, Sulfolobus solfataricus (DSM 5837) and Thermus thermophilus (ATCC 27634) were prepared as reported in 2b. PNP-α and β-glucoside were used as donors of carbohydrate moiety. Work-up and purification procedures are the same as reported in 2a.
7. 5.Vic, G., Crout, D.H.G.,Tetrahedron Asymmetry 1994 5, 2513-2516
8. 6. Azzena, F., Calvani, F., Crotti, P., Gardelli, G., Macchia, F., Pineschi, M. Tetrahedron, 1995 51 10601-10626
9. 3).
10. 3), enzymatic transglycosydation (almond β-glucosidase or Thermus thermophilus α-glucosidase), and hydrogenolysis obtaining 8 or 9 and acetylation for the synthesis of 6 and 7.
11. 9. Grandjean, D., Pale, P., Chuche, J. Tetrahedron Letters 1991 32, 3043-3046
12. 10. Vantitten, E., Kanerva, T.L. Tetrahedron: Asymmetry 1992 3, 1529-1532
13. 11. Anzeveno, P.B. Greemer, L.J., Daniel, J.K., King, C.H., Liu, P.S. J. Org. Chem. 1989 54 2539-2542
14. 12. Henderson, I., Laslo, K., Wong, C-H Tetrahedron Letters 1994 35, 359-362