Haloalkane dehalogenase catalysed desymmetrisation and tandem kinetic resolution for the preparation of chiral haloalcohols

Mohangic Acids A–E, p-Aminoacetophenonic Acids from a Marine-Mudflat-Derived Streptomyces sp.

“…The solvent was removed, and the dibromopropane was purified by column chromatography (silica gel, 40–63 μm, pentane). With the acquired dibromopropane, bidentate chiral solvents ( R , R )-and ( S , S )-bis-α-methylbenzylamine- p -Me were synthesized according to previously reported procedures. , …”

Inverting hydrolases and their use in enantioconvergent biotransformations

“…Carefully designed mutants giving ( R )-2,3-dichloropropan-1-ol in 90% ee and the ( S )-enantiomer in 97% ee could be obtained from a screening of only 5500 variants after five rounds of evolution. Recently, a one-enzyme tandem-desymmetrization/kinetic resolution process of short-chain prochiral and meso -dihaloalkanes was shown [92]. In this protocol, the dihaloalkane was converted to the haloalcohol in a first step, which was further dehalogenated to the corresponding diol.…”

Enhancement of (S)-2,3-dichloro-1-propanol production by recombinant whole-cell biocatalyst in n-heptane–aqueous biphasic system

“…Enantiopure haloalcohols are extensively used as chiral building blocks for the production of many industrially important chemicals such as pharmaceuticals and pesticides (Pamies and Backvall, 2002;Tanis et al, 2006;Westerbeek et al, 2012). For example, chiral haloalcohol (S)-2,3-dichloro-1-propanol ((S)-DCP) serves as a key precursor for the synthesis of (R)-epichlorohydrins, ␤-blockers, lcarnitine and platelet activating factor (PAF) (Furnodewinter et al, 1991;Kasai et al, 1992a,b;Li et al, 2011b;Yang et al, 2011).…”