A simple and efficient one-step, regioselective, enzymatic glucosylation of arbutin by α-glucosidase

Tetrahedron Letters

Volumn 48, Issue 40, 2007, Pages 7222-7224

  Milosavić, Nenad B ^a   Prodanović, Radivoje M ^b   Jankov, Ratko M ^b  

^a UNIVERSITY OF BELGRADE   (Serbia)

^b UNIVERSITY OF BELGRADE   (Serbia)

Author keywords

Anomer selective glucosylation; 4 Hydroxyphenyl isomaltoside; Enzyme reactions; Maltase; Transglucosylation

Indexed keywords

4 HYDROXYPHENYL BETA ISOMALTOSIDE; ALPHA GLUCOSIDASE; ARBUTIN; BUFFER; CARBOHYDRATE DERIVATIVE; CITRATE SODIUM; GLUCOSIDE; ISOMALTOSE; SODIUM DIHYDROGEN PHOSPHATE; SUCROSE; UNCLASSIFIED DRUG;

ACIDITY; ARTICLE; ENZYME MECHANISM; ENZYME SYNTHESIS; GLYCOSYLATION; MOLECULE; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 34548409004     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.07.152     Document Type: Article

References (16)

1. Yasukochi T., Inaba C., Fukase K., and Kusumoto S. Tetrahedron Lett. 40 (1999) 6585-6589
2. Wong C.H., and Whitesides G.M. Enzymes in Synthetic Organic Chemistry (1994), Pergamon Press, Oxford pp 252-311
3. Bassao A., Ducret A., Gardossi L., and Lortie R. Tetrahedron Lett. 43 (2002) 2005-2008
4. Akita H., Kurashima K., Nakamura T., and Kato K. Tetrahedron: Asymmetry 10 (1999) 2429-2439
5. Akita H., Kawahara E., Kishida M., and Kato K. J. Mol. Catal. B: Enzym. 40 (2006) 8-15
6. Nakagawa H., Yoshiyama M., Shimura S., Usami K., and Kirimura S. Biosci. Biotechnol. Biochem. 62 (1998) 1332-1339
7. Kosary J., Stefanovits-Banyai E., and Boross L. J. Biotechnol. 66 (1998) 83-90
8. Maeda K., and Fukuda M. J. Pharmacol. Exp. Ther. 276 (1996) 756-769
9. Prodanovic R.M., Milosavic N.B., Sladic D., Cirkovic Velickovic T., and Vujcic Z. Biotechnol. Lett. 27 (2005) 551-554
10. Prodanovic R., Milosavic N., Sladic D., Zlatovic M., Bozic B., Velickovic Cirkovic T., and Vujcic Z. J. Mol. Catal. B: Enzym. 35 (2005) 142-146
11. Kurosum J., Sato T., Yoshida K., Tsugane T., Shimura S., Kirimura K., Kino K., and Usami J. J. Biosci. Bioeng. 93 (2002) 328-330
12. Sugimoto K., Nishimura T., Nomura K., Sugimoto K., and Kuriki T. Chem. Pharm. Bull. 51 (2003) 798-801
13. Sugimoto K., Nomura K., Nishimura T., Kiso T., Sugimoto K., and Kuriki T. J. Biosci. Bioeng. 99 (2005) 272-276
14. Shin K.H., Kong Y.J., Lee D.J., and Lee H.T. Biotechnol. Lett. 22 (2000) 321-325
15. Prodanovic R., Milosavic N., Jovanovic S., Prodanovic O., Cirkovic-Velickovic T., Vujcic Z., and Jankov R.M. Biocat. Biotrans. 24 (2006) 195-200
16. 1H NMR (200 MHz, DMSO) 6.92 (d, 2H, J = 9.0 Hz, H-2, H-6), 6.68 (d, 2H, J = 9.0 Hz, H-3, H-5), 4.68 (d, 1H, J = 3.6 Hz, H-1′), 4.57 (d, 1H, J = 6.6 Hz, H-1″), 3.10-3.70 (m, 12 H, H-2′, H-2″ H-3′, H-3″, H-4′, H-4″, H-5′, H-5″, H-6′A, H-6′B, H-6″, H-6″B).