Chemical and enzymatic synthesis of glycoconjugates 4. Control of regioselectivity in high yielding synthesis of (β-D-fucopyranosyl)-O-D- xylopyranosyl disaccharides using a CLONEZYME(TM) thermophilic glycosidase

Tetrahedron Letters

Volumn 39, Issue 49, 1998, Pages 8963-8966

  Li, Jun ^a   Robertson, Dan E ^b   Short, Jay M ^b   Wang, Peng George ^a  

^a WAYNE STATE UNIVERSITY   (United States)

^b DIVERSA CORPORATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOCONJUGATE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; GLYCOSYLATION; STEREOCHEMISTRY; STEREOSPECIFICITY; SYNTHESIS;

EID: 0032480938     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02072-3     Document Type: Article

References (16)

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2. 2. (a) Ruggeri, G. D.; Nigrelli, R. F. Physiologically Active Substances from Echinoderms. In Bioactive Compounds from the Sea; Humm, H. J.; Lane, C. E. Eds.; Marcel Dekker: New York, 1974; Marine Science Series, Vol 1, pp 183-195.
3. (b) Dubois, M. A.; Higuchi, R.; Komori, T.; Sasaki, T. Liebigs Ann. Chem. 1988, 845.
4. 3. (a) Roccatagliata, A. J.; Maier, M. S.; Seldes, A. M.; Iorizzi, M.; Minale, L. J. Nat. Prod. 1994, 57, 747.
5. (b) Iorizzi, M.; Bifulco, G.; De Riccardia, F.; Minale, L.; Riccio, R.; Zollo, F. J. Nat Prod. 1995, 58, 10.
6. 4. Iorizzi, M.; Bryan, P.; McClintock, J.; Minale, L.; Palagiano, E.; Maurell, S.; Riccio, R.; Zollo, F. J. Nat Prod. 1995, 58, 653.
7. 5. (a) Nilsson, K. G. I. Synthesis with Glycosidases In Modern Methods in Carbohydrate Synthesis; Khan, S. H.; O'Neill, R. A. Eds.; Harwood Academic Publishers: The Netherlands, 1996, pp518-547.
8. (b) Fernández-Mayoralas, A. Top. Curr. Chem. 1997, 186, 1.
9. (c) Murata, T.; Usui, T. Biosci. Biotech. Biochem. 1997, 61, 1059.
10. (d) Crout, D. H. G.; Vic, G. Curr. Opin. Chem. Bio. 1998, 2, 98.
11. 6. (a) Li, J.; Wang, P. G. Tetrahedron Lett. 1997, 38, 7967.
12. (b) Fang, J.; Xie, W.; Li, J. Wang, P. G. Tetrahedron Lett. 1998, 39, 919.
13. 7. (a) Nilsson, K. G. I. Carbohydr. Res. 1987, 167, 95.
14. (b) Nilsson, K. G. I. Carbohydr. Res. 1989, 188, 9.
15. 8. Löpez, R.; Fernández-Mayoralas, A. J. Org. Chem. 1994, 59, 737.
16. 3) δ 5.20 (d, 1H, J = 3.6 Hz, H-4'), 5.11 (dd, 1H, J = 8, 10.4 Hz, H-2'), 4.97 (dd, 1H, J = 3.6, 10.4 Hz, H-3'), 4.89 (td, 1H, J = 6.4, 4.4 Hz, H-4), 4.82 (dd, 1H, J = 4.8, 6.4 Hz, H-2), 4.57 (d, 1H, J = 8 Hz, H-1'), 4.40 (d, 1H, J = 4.8 Hz, H-1), 4.09 (dd, 1H, J = 4.0, 12.4 Hz, H-5e), 3.87 (t, 1H, J = 6.4 Hz, H-3), 3.78 (q, 1H, J = 6.4 Hz, H-5'), 3.45 (dd, 1H, J = 6.0, 12.0 Hz, H-5a), 3.4 (s, 3H, OMe), 2.17, 2.12, 2.09, 2.05, 1.98 (5s, 15H, acetyl), 1.20 (d, 3H, J = 6.4 Hz, H-6'). 6a : δ 5.21 (d, 1H, J = 3.6 Hz, H-4'), 5.14 (dd, 1H, J = 8, 10.4 Hz, H-2'), 5.12 (t, J =8.0 Hz, H-3), 4.97 (dd, 1H, J = 3.6, 10.4 Hz, H-3'), 4.85 (td, 1H, J = 8.0, 4.8 Hz, H-4), 4.69 (d, 1H, J = 8 Hz, H-1'), 4.52 (d, 1H, J = 6.0 Hz, H-1), 4.04 (dd, 1H, J = 5.2, 12.4 Hz, H-5e), 3.81 (q, 1H, J = 6.4 Hz, H-5'), 3.61 (dd, 1H, J = 5.6, 8.0 Hz, H-2), 3.49 (s, 3H, OMe), 3.41 (dd, 1H, J = 7.6, 12 Hz, H-5a), 2.17, 2.08, 2.06, 2.05, 1.97 (5s, 15H, acetyl), 1.22 (d, 3 H, J = 6.4 Hz, H-6'). 5b : δ 7.35-7.27 (m, 5H), 5.19 (dd, 1H, J = 3.2, 1.2 Hz, H-4'), 5.11 (dd, 1H, J = 8, 10.4 Hz, H-2'), 4.97-4.91 (m, 3H, H-3', H-4 and H-2), 4.80 (d, 1H, J = 12.4 Hz, benzylic proton), 4.56 (d, 1H, J = 12.8 Hz, benzylic proton), 4.55 (d, 1H, J = 7.6 Hz, H-1'), 4.49 (d, 1H, J = 6.0 Hz, H-1), 4.13 (dd, 1H, J = 4.8, 12.4 Hz, H-5e), 3.85 (t, 1H, J = 7.0 Hz, H-3), 3.76 (qd, 1H, J = 6.4, 1.2 Hz, H-5'), 3.40 (dd, 1H, J = 7.2, 12.4 Hz, H-5a), 2.17, 2.074, 2.07, 1.98, 1.97 (5s, 15H, acetyl), 1.19 (d, 3H, J = 6.4 Hz, H-6'). 6b : δ 7.41-7.29 (m, 5 H), 5.18-5.15 (m, 2H, H-4' & H-2'), 5.13 (t, J =8.0 Hz, H-3), 4.93 (dd, 1H, J = 3.2, 10.4 Hz, H-3'), 4.91 (d, 1H, J = 12.0 Hz, benzylic proton), 4.87 (td, 1H, J = 7.6, 4.8 Hz, H-4), 4.73 (d, 1H, J = 5.6 Hz, H-1), 4.67 (d, 1H, J = 8.0 Hz, H-1'), 4.58 (d, 1H, J = 11.6 Hz, benzylic proton), 4.10 (dd, 1H, J = 4.8, 12.0 Hz, H-5e), 3.73 (dd, 1H, J = 5.6, 8.0 Hz, H-2), 3.63 (q, 1H, J = 6.4 Hz, H-5'), 3.44 (dd, 1H, J = 7.6, 12 Hz, H-5a), 2.17, 2.08, 2.052, 2.05, 1.97 (5s, 15H, acetyl), 1.12 (d, 3H, J = 6.4 Hz, H-6'). 5e : δ 7.47-7.44 (m, 5H), 5.19 (dd, 1H, J = 3.6, 1.2 Hz, H-4'), 5.08 (dd, 1H, J = 7.8, 10.5 Hz, H-2'),4.99-4.91 (m, 3H, H-3', H-4 and H-1), 4.80 (dd, 1H, J = 3.9, 9.9 Hz, H-2), 4.73 (d, 1H, J = 11.7 Hz, benzylic proton), 4.58 (d, 1H, J = 8.1 Hz, H-1'), 4.48 (d, 1H, J = 12.0 Hz, benzylic proton), 4.13 (t, 1H, J = 9.6 Hz, H-3), 3.82-3.73 (m, 2H, H-5e, H-5'), 3.63 (t, 1H, J = 10.5 Hz, H-Sa), 2.16, 2.10, 2.05, 1.97, 1.96 (5s, 15H, acetyl), 1.18 (d, 3H, J = 6.3 Hz, H-6'). 6c : δ .41-7.27 (m, 5 H), 5.49 (t, J =9.6 Hz, H-3), 5.20 (d, 1H, J = 2.7, H-4'), 5.19 (dd, 1H, J=7.8, 10.5 Hz, H-2'), 5.01 (d, 1H, J = 3.3 Hz, H-1), 4.95 (dd, 1H, J = 3.6, 10.5 Hz, H-3'), 4.91 (td, 1H, J = 10.5, 6.6 Hz, H-4), 4.75 (d, 1H, J = 12.6 Hz, benzylic proton), 4.62 (d, 1H, J = 12.3 Hz, benzylic proton), 4.57 (d, 1H, J = 7.8 Hz, H-1'), 3.77-3.70 (m, 3H, H-5', H-5e and H-2), 3.66 (t, 1H, J = 10.5 Hz, H-5a), 2.18, 2,07, 2.03, 2.00, 1.98 (5s, 15H, acetyl), 1.12 (d, 3 H, J = 6.6 Hz, H-6').