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200517.fm Page 37 Friday, March 18, 2005 2:52 PM
2005
Biochemical syntheses
O 0035
Highly Enantioselective sec-Alkyl Sulfatase Activity of Sulfolobus acidocaldarius
639. — Treatment of racemic sulfates (I) with whole cells of the title sulfatase
17- 037 DSM
leads to hydrolysis of the (R)-enantiomers to provide the (S)-configurated sec-alcohols,
and thus furnishing a homochiral product mixture. High enantioselectivities are
observed for sulfates (Ia) and (Id), bearing two significantly sterically varying groups
R1 and R2. Sulfates (Ib) and (Ic) bearing the sulfate group more in the center of the molecule give decreased enantioselectivities. Compared to known Rhodococcus sulfatase
RS2, the present sulfatase affords enhanced enantioselectivities and accepts a wider
substrate spectrum. — (WALLNER, S. R.; NESTL, B. M.; FABER*, K.; Org. Lett. 6
(2004) 26, 5009-5010; Inst. Chem., Org. Bioorg. Chem., Karl Franzens Univ. Graz,
A-8010 Graz, Austria; Eng.) — Klein
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