Diastereoselective and regioselective reactions on D-aldopentose mixtures: A possible reason for nature's choice of D-ribofuranose based nucleic acids?

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 15, 1997, Pages 1999-2002

  Wengel, Jesper ^a   Scheuer Larsen, Claus ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

ARABINOSE; LYXOSE; RIBOSE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG; XYLOSE;

ARTICLE; CARBOHYDRATE ANALYSIS; CARBOHYDRATE SYNTHESIS; CHEMICAL STRUCTURE; CHIRALITY; ENZYME ACTIVITY; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY;

EID: 0030791343     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)00352-1     Document Type: Article

References (18)

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2. Boisen, A.; Dalskov, J; Wengel, J. Unpublished results.
3. Eschenmoser, A.; Kisakürek, M. V. Helv. Chim. Acta 1996, 79, 1249.
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9. This lipase is commercially available from Novo-Nordisk A/S, Bagsvœrd, Denmark.
10. 3): δ 63.5, 64.9, 70.5, 70.6, 71.0, 74.9, 79.7, 80.1, 96.0, 101.2, 173.4, 173.7. Calcd. C: 49.08; H: 7.32; Found C: 48.89; H: 7.02%.
11. 2SO): δ 55.1, 64.3, 65.9, 70.6, 70.8, 71.3, 75.4, 80.6, 81.1, 85.3, 96.5, 101.7. Calcd. C: 69.01; H: 6.24; Found C: 69.37; H: 6.22%.
12. Moris, F.; Gotor, V. J. Org. Chem. 1993, 58, 653.
13. See, e.g.: von Büren, M.; Petersen, G. V.; Rasmussen, K.; Brandenburg, G.; Wengel, J. Tetrahedron 1995, 51, 8491.
14. 2O.
15. The selectivity obtained here during 4,4′-dimethoxytritylation could not be repeated during tritylations. See also an earlier report describing selective 5-O-tritylations of D-ribose, D-arabinose, D-xylose and D-lyxose in separate reactions using trityl chloride in anhydrous pyridine at room temperature: Kam, B. L.; Oppenheimer, N. J. Carbohydr. Res. 1979, 69, 308. Synthesis of 2-deoxy-5-O-(4,4′-dimethoxytrityl)-D-ribofuranose from 2-deoxy-D-ribose using a similar procedure has been reported: Groebke, K.; Leumann, C. Helv. Chim. Acta. 1990, 73, 608.
16. The selectivity obtained here during 4,4′-dimethoxytritylation could not be repeated during tritylations. See also an earlier report describing selective 5-O-tritylations of D-ribose, D-arabinose, D-xylose and D-lyxose in separate reactions using trityl chloride in anhydrous pyridine at room temperature: Kam, B. L.; Oppenheimer, N. J. Carbohydr. Res. 1979, 69, 308. Synthesis of 2-deoxy-5-O-(4,4′-dimethoxytrityl)-D-ribofuranose from 2-deoxy-D-ribose using a similar procedure has been reported: Groebke, K.; Leumann, C. Helv. Chim. Acta. 1990, 73, 608.
17. Pitsch, S.; Krishnamurthy, R.; Bolli, M.; Wendeborn, S.; Holzer, A.; Minton, M.; Lesueur, C.; Schlönvogt, I.; Jaun, B.; Eschenmoser, A. Helv. Chim. Acta. 1995, 78, 1621.
18. Knerr, L.; Pannecoucke, X.; Schmitt, G.; Luu, B. Tetrahedron Lett. 1996, 37, 5123.