Journal
NATURE COMMUNICATIONS
Volume 7, Issue -, Pages -Publisher
NATURE PUBLISHING GROUP
DOI: 10.1038/ncomms11917
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Funding
- Chemical and Pharmaceutical Engineering (CPE) Program from Singapore-MIT Alliance
- Science & Engineering Research Council of A*STAR, Singapore [1021010026]
- Synthetic Biology for Clinical and Technological Innovation (SynCTI) program from National University of Singapore
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New types of asymmetric functionalizations of alkenes are highly desirable for chemical synthesis. Here, we develop three novel types of regio- and enantioselective multiple oxy- and amino-functionalizations of terminal alkenes via cascade biocatalysis to produce chiral alpha-hydroxy acids, 1,2-amino alcohols and alpha-amino acids, respectively. Basic enzyme modules 1-4 are developed to convert alkenes to (S)-1,2-diols, (S)-1,2-diols to (S)-alpha-hydroxyacids, (S)-1,2-diols to (S)-aminoalcohols and (S)-alpha-hydroxyacids to (S)-alpha-aminoacids, respectively. Engineering of enzyme modules 1 & 2, 1 & 3 and 1, 2 & 4 in Escherichia coli affords three biocatalysts over-expressing 4-8 enzymes for one-pot conversion of styrenes to the corresponding (S)-alpha-hydroxyacids, (S)-aminoalcohols and (S)-alpha-aminoacids in high e.e. and high yields, respectively. The new types of asymmetric alkene functionalizations provide green, safe and useful alternatives to the chemical syntheses of these compounds. The modular approach for engineering multi-step cascade biocatalysis is useful for developing other new types of one-pot biotransformations for chemical synthesis.
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