Novel deoxy-selenylconduritols: chemoenzymatic synthesis and biological evaluation

The first synthesis of two selenyldeoxycyclitols (4-bromo-2-phenylselenyl conduritol F and 6-phenylselenylconduritol F) is reported via a chemoenzymatic enantioselective route. The key step of the synthesis is the selenolysis of a vinyl epoxide. The new compounds were evaluated for their capacity to inhibit the growth of different microorganisms using a modification of the agar diffusion technique with thin layer chromatography plates as support.

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(1S,2S,5S,6S)-4-Bromo-2-phenylselenyl-5,6-O-isopropylidenedioxycyclohex-3-ene-1-olC15H17O3SeBrEe >98%[α]D25=+168 (c 0.6, CH2Cl2)Source of chirality: enzymatic catalysisAbsolute configuration: (1S,2S,5S,6S)

(1S,2S,5S,6S)-4-Bromo-6-(phenylselenyl)cyclohex-4-ene-1,2,3-triolC12H13O3SeBrEe >98%[α]D20=+93 (c 0.2, MeOH)Source of chirality: enzymatic catalysisAbsolute configuration: (1S,2S,5S,6S)

(1S,2S,5R,6S)-2-Phenylselenyl-5,6-isopropylidenedioxycyclohex-3-ene-1-olC15H18O3SeEe >98%[α]D20=+127 (c 1.1, CH2Cl2)Source of chirality: enzymatic catalysisAbsolute configuration: (1S,2S,5R,6S)

(1S,2R,3R,6S)-6-(Phenylselenyl)cyclohex-4-ene-1,2,3-triol (phenylselenylconduritol F)C12H14O3SeEe >98%[α]D20=+71 (c 0.2, MeOH)Source of chirality: enzymatic catalysisAbsolute configuration: (1S,2R,3R,6S)