β-glycosidases: Tools for chiral discrimination

Chirality

Volumn 11, Issue 5-6, 1999, Pages 451-458

  Zarevúcka, Marie ^a   Vacek, Miroslav ^b   Kuldová, Jelena ^b   Šaman, David ^a   Wimmer, ZdeněK ^a   Weignerova, Lenka ^c   Kren, Vladimir ^c  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^b INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

^c INSTITUTE OF MICROBIOLOGY   (Czech Republic)

Author keywords

galactosidases from Escherichia coli, Bacillus circulans, and Kluyveromyces lactis; glucosidase from almond; Absolute configuration; Alkyl D glycopyranoside; Diastereoisomeric excess; Enantioselectivity; Saccharomyces cerevisiae; Tenebrio molitor

Indexed keywords

BETA GALACTOSIDASE; BETA GLYCOSIDASE; GLYCOSIDASE; UNCLASSIFIED DRUG;

CARBON NUCLEAR MAGNETIC RESONANCE; CHIRALITY; CIS TRANS ISOMERISM; CONFERENCE PAPER; DIASTEREOISOMER; GLYCOSYLATION; HYDROLYSIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0345161700     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1999)11:5/6<451::AID-CHIR16>3.0.CO;2-D     Document Type: Conference Paper

References (20)

1. Werschkun B, König WA, Křen V, Thiem J. Substrate structure and incubation-parameter-dependent selectivities in chiral discrimination of galactopyranosides by β-galactosidase hydrolysis. J Chem Soc Perkin Trans 1995;12459-2466.
2. Křen V, Thiem J. Glycosylation employing bio-systems: from enzymes to whole cells. Chem Soc Rev 1997;26:463-473.
3. Björkling F, Godtfredsen SE. New enzyme catalyzed synthesis of monoacyl galactoglycerides. Tetrahedron 1988;44:2957-2962.
4. Gais HJ, Zeissler A, Maindonis P. Diastereoselective D-galactopyranosyl transfer to meso diols catalyzed by β-galactosidases. Tetrahedron Lett 1988;29:5743-5444.
5. 13C NMR spectroscopy of the resulting mono-D-glycopyranosides. Carbohydr Res 1980;87:27-34.
6. Wimmer Z, Rejzek M, Zarevúcka M, Kuldová J, Hrdý I, Němec V, Romaňuk M. A series of bicyclic insect juvenile hormone analogs of Czech origin: twenty years of development. J Chem Ecol 1997;23:605-628.
7. Slàma K, Romaňuk M, Šorm F. Insect hormones and bioanalogues. Vienna: Springer; 1974. p 90-137.
8. Wimmer Z, Streinz L, Romaňuk M. Preparation of carbamate derivatives of 2-(4-hydroxybenzyl)-1-cyclohexanone with a juvenoid activity. Collect Czech Chem Commun 1985;50:2543-2546.
9. Wimmer Z, Buděšínský M, Macek T, Svatoš A, Šaman D, Vašíčková S, Romaňuk M. Biotransformation of 2-(4-methoxybenzyl)-1-cyclohexanone by means of Saccharomyces cerevisiae. Collect Czech Chem Commun 1987;52:2326-2337.
10. Zarevúcka M, Vacek M, Wimmer Z, Demnerová K, Macková M. A chemoenzymatic synthesis of the O-glycosides. Chirality 1998;10:676-681.
11. Rinaldi PL. The determination of absolute configuration using nuclear magnetic resonance techniques. Prog Nucl Magn Reson Spectrosc 1982;15:291-351.
12. Dale JA, Dull DL, Mosher HS. α-Methoxy-α-trifluoromethylphenylacetic acid, a versatile reagent for determination of enantiomeric composition of alcohols and amines. J Org Chem 1969;34:2543-2549.
13. Dale JA, Mosher HS. Enantiomeric purity of phenylethylene glycol and reliability of phenylglyoxylate asymmetric reduction in configurational assignment. J Org Chem 1970;35:4002-4003.
14. Dale JA, Mosher HS. Nuclear magnetic resonance enantiomer reagent. Configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O-methylmandelate, and α-methoxy-α-trifluoromethylphenyl acetate (MTPA) esters. J Am Chem Soc 1973;95:512-519.
15. Minamikawa J, Brossi A. Selective O-demethylation of an aromatic methylester in the presence of an aromatic methylenedioxy group with trimethyliodide in quinoline. Tetrahedron Lett 1978;3085-3086.
16. 19F chemical shifts of α-methoxy-α-trifluoromethylphenyl acetate derivatives. J Org Chem 1973;38:2143-2147.
17. Rejzek M, Wimmer Z, Zarevúcka M, Šaman D, Pavlik M, Říčánková M. Chiral juvenoids derived from 2-substituted cyclohexanols. Tetrahedron Asym 1994;5:1501-1512.
18. Zarevúcka M, Rejzek M, Wimmer Z, Šaman D, Streinz L. Chiral precursors of optically active juvenoids. Terahedron 1993;49:5305-5314.
19. Wimmer Z, Vaněk T, Macek T, Šaman D, Svatoš A. Reduction of 2-substituted cyclohexanones by Saccharomyces cerevisiae under aerobic and anaerobic conditions. Enzyme Microb Technol 1992;14:197-202.
20. Zarevúcka M, Rejzek M, Šaman D, Streinz L, Wimmer Z. Reduction of 2-substituted cyclohexanones by Saccharomyces cerevisiae. Biocatal Biotrans 1996;13:233-243.