Highly regio- and enantio-selective deacylation of carbocyclic 3',5'- di-O-acyloxetanocins by lipases

Tetrahedron Letters

Volumn 39, Issue 17, 1998, Pages 2613-2616

  Katagiri, Nobuya ^a   Morishita, Yoshihiro ^a   Yamaguchi, Masahiko ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

3',5' DI O ACYLOXETANOCIN A; 3',5' DI O ACYLOXETANOCIN T; OXETANOCIN DERIVATIVE; SOLVENT; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; ARTICLE; BACILLUS MEGATERIUM; CHEMICAL REACTION; DEACYLATION; DRUG ISOLATION; DRUG STRUCTURE; ENZYME ACTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN;

BACILLUS MEGATERIUM;

EID: 0032559982     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00282-2     Document Type: Article

References (23)

1. 1. Part ILIII of "Synthesis of nucleosides and their related compounds". For Part ILII, see: Katagiri, N.; Kokufuda, H.; Makino, M.; Vince, R.; Kaneko, C. Nucleosides & Nucleotides, in press, 1997.
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4. 3. For recent reviews of the synthesis of carbocyclic nucleosides, see: (a) Borthwick, A. D.; Biggadike, K. Tetrahedron 1992,48, 571.
5. (b) Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611.
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8. 5. Regioselective acylation and deacylation of natural nucleosides by lipases have been reported. (a) Uemura, A.; Nozaki, K.; Yamashita, J.; Yasumoto, M. Tetrahedron Lett. 1989, 30, 3817.
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11. (d) idem, ibid, 1993, 58, 653.
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13. 3).
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16. 8. Lipase type I, VII, and XIII were purchased from Sigma.
17. 3).
18. 3).
19. 2O)]. Bisacchi, G. S.; Breitman, A.; Cianci, C. W.; Clark, J. M.; Field, A. K.; Hagen, M. E.; Hockstein, D. R.; Malley, M. F.; Mitt, T.; Slusarchyk, W. A.; Sundeen, J. E.; Terry, B. J.; Tuomari, A. V.; Weaver, E. R.; Young, M. G.; Zahler, R. J. Med. Chem. 1991, 34, 1415.
20. 3).
21. 13. Compound (±)-3a was synthesized by the method previously reported. Katagiri, N.; Sato, H.; Kaneko, C. Chem. Pharm. Bull. 1990, 38, 288.
22. 3). The e.e. was determined by HPLC analysis using Chiralpak AS (hexane-EtOH = 1:1).
23. 3).