Synthesis of a ribofuranosyl cation mimic

Tetrahedron Letters

Volumn 37, Issue 12, 1996, Pages 2097-2100

  Bols, Mikael ^a   Persson, Morten P ^b   Butt, Waqas M ^b   Jørgensen, Martin ^b   Christensen, Peter ^b   Hansen, Lars T ^b  

^a AARHUS UNIVERSITY   (Denmark)

^b TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

5 HYDROXYISOFAGAMINE; ALPHA GLUCOSIDASE; BETA GLUCOSIDASE; ISOFAGAMINE; NUCLEOSIDE PHOSPHORYLASE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BLOOD; CHIRALITY; CONTROLLED STUDY; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN TISSUE; PLANT; REACTION ANALYSIS; STEREOCHEMISTRY; YEAST;

EID: 0029878043     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00202-X     Document Type: Article

References (14)

1. Raymond, J. -L.; Janda, K. D.; Lerner, R. A. Angew. Chem. 1991 103 1690-1.
2. Jespersen, T. M.; Dong, W.; Sierks, M. R.; Skrydstrup, T.; Lundt, I.; Bols, M. Angew. Chem. Int. Ed. Engl. 1994 33 1778-9.
3. Ichikawa, Y.; Igarashi, Y. Tetrahedron Lett. 1995 36 4585-6.
4. Ho, P. T. Can. J. Chem. 1979 57 381-3.
5. Schmidt, O.T. Methods Carbohydr. Chem. 1963 2 318-25.
6. 2C 3/10 56.9 95.0 84.9 54.3 - 65.9 114.2 28.6 27.7 4/11 53.5 80.8 72.4 50.8 - 65.1 -6 50.2 81.6 78.0 67.5 48.3 65.4 111.7 29.7 28.8
7. Ichikawa, M.; Igarashi, Y.; Ichikawa, Y. Tetrahedron Lett. 1995 36 1767-1770.
8. Spectral data of 7 equivalent to reported values (ref 7).
9. Hughes, N. A.; Speakman, P. R. H. Carbohydr. Res. 1965 1 171-5.
10. α-glucosidase assay was performed according to Halvorson, H.O. Methods Enzymol. 1966 8 559-562. The type 1 bakers yeast enzyme (Sigma G 5003) was employed to catalyse hydrolysis of 4-nitrophenyl α-D-glucopyranoside to glucose and 4-nitrophenol at pH 6.8 and 22°C with or without inhibitor present. Formation of 4-nitrophenol was followed spectrophotometrically at 400 nm.
11. β-glucosidase assay was performed according to Halvorson, H.O. Methods Enzymol. 1966 8 559-562. The enzyme from almonds (Sigma G 0395) was employed to catalyse hydrolysis of 4-nitrophenyl β-D-glucopyranoside to glucose and 4-nitrophenol at pH 6.8 and 22°C with or without inhibitor present. Formation of 4-nitrophenol was followed spectrophotometrically at 400 nm.
12. PNP'ase assay was performed according to Stoeckler, J.D.; Agarval, R.P.; Agarwal, K.C.; Parks, R.E. Jr. Methods Enzymol. 1978 51 530-8. Purin nucleoside phosphorylase from human blood (Sigma N 3514) was employed to catalyse phosphorolysis of inosine to α-D-ribofuranose-1-phosphate and hypoxanthine at pH 7.5 and 22°C in the presence of xanthine oxidase (Sigma X 4875) with or without inhibitor present (see below). Xanthine oxidase catalysed the immidiate oxidation of hypoxanthine to uric acid, formation of which was followed UV-spectrophotometrically at 293 nm.
13. (equation presented)
14. Since the PNP'ase assay relies on two enzymes it is important to ensure which enzyme is being affected by an inhibitor. Compound 4 did not inhibit xanthine oxidase at the contrations ([4] = 1.1 mM) at which the PNP'ase inhibition study was carried out.