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Diastereoselective synthesis of (R) - (alkyl) -beta-D-galactopyranoside by using beta-galactosidase (Aspergillus oryzae) in low-water media

Majumder, A.B.; Singh, B.; Gupta, M.N.

Bioorganic and Medicinal Chemistry Letters 18(1): 124-128

2008

ISSN/ISBN: 1464-3405
PMID: 18024031
DOI: 10.1016/j.bmcl.2007.11.006
Accession: 052591850
A beta-galactosidase (from Aspergillus oryzae) preparation viz. EPRP (enzyme precipitated and rinsed with propanol), obtained by the removal of bulk water by precipitation with n-propanol, showed higher biological activity than the lyophilized powder. FT-IR study confirmed that EPRP had retained the alpha-helical content of the native structure better than the lyophilized form. Use of this formulation of beta-galactosidase under low water conditions (temperature 55 degrees C, reaction time of 4 h) gave enantioselectivity, E > 1000 for the stereoselective synthesis of (R)-(1-phenylethyl)-beta-D-galactopyranoside, starting from racemic 1-phenylethanol and D-galactose. For racemic 2-octanol also, EPRP worked better. Under similar conditions, (R)-(2-octyl)-beta-D-galactopyranoside was formed with an enantioselectivity, E = 38.

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Related References

Ooi, Y.; Hashimoto, T.; Mitsuo, N.; Satoh, T. 1985: Enzymic formation of beta alkyl glycosides by beta galactosidase from aspergillus oryzae and its application to the synthesis of chemically unstable cardiac glycosides Chemical and Pharmaceutical Bulletin 33(5): 1808-1814
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