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      The Pictet-Spengler Reaction in Nature and in Organic Chemistry

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      Journal: Angewandte Chemie International Edition
      Publisher: Wiley-Blackwell

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          Chemistry and biology of the tetrahydroisoquinoline antitumor antibiotics.

          Jack D Scott, Robert M Williams (2002)
          Article 0 comments Cited 172 times – based on 0 reviews     Review now
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            The Pictet-Spengler condensation: a new direction for an old reaction

            Eric D Cox, James Cook (1995)
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              Metabolic engineering of taxadiene biosynthesis in yeast as a first step towards Taxol (Paclitaxel) production.

              Benedikt Engels, Pia Dahm, Stefan Jennewein (2008)
              Metabolic engineering in microbes could be used to produce large amounts of valuable metabolites that are difficult to extract from their natural sources and too expensive or complex to produce by chemical synthesis. As a step towards the production of Taxol in the yeast Saccharomyces cerevisiae, we introduced heterologous genes encoding biosynthetic enzymes from the early part of the taxoid biosynthetic pathway, isoprenoid pathway, as well as a regulatory factor to inhibit competitive pathways, and studied their impact on taxadiene synthesis. Expression of Taxus chinensis taxadiene synthase alone did not increase taxadiene levels because of insufficient levels of the universal diterpenoid precursor geranylgeranyl diphosphate. Coexpression of T. chinensis taxadiene synthase and geranylgeranyl diphosphate synthase failed to increase levels, probably due to steroid-based negative feedback, so we also expressed a truncated version of 3-hydroxyl-3-methylglutaryl-CoA reductase (HMG-CoA reductase) isoenzyme 1 that is not subject to feedback inhibition and a mutant regulatory protein, UPC2-1, to allow steroid uptake under aerobic conditions, resulting in a 50% increase in taxadiene. Finally, we replaced the T. chinensis geranylgeranyl diphosphate synthase with its counterpart from Sulfolobus acidocaldarius, which does not compete with steroid synthesis, and codon optimized the T. chinensis taxadiene synthase gene to ensure high-level expression, resulting in a 40-fold increase in taxadiene to 8.7+/-0.85mg/l as well as significant amounts of geranylgeraniol (33.1+/-5.6mg/l), suggesting taxadiene levels could be increased even further. This is the first demonstration of such enhanced taxadiene levels in yeast and offers the prospect for Taxol production in recombinant microbes.
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                Author and article information

                Journal
                Title: Angewandte Chemie International Edition
                Abbreviated Title: Angew. Chem. Int. Ed.
                Publisher: Wiley-Blackwell
                ISSN: 14337851
                Publication date Created: September 05 2011
                Publication date (Print): September 05 2011
                Volume: 50
                Issue: 37
                Pages: 8538-8564
                Article
                DOI: 10.1002/anie.201008071
                PubMed ID: 21830283
                SO-VID: 33a065ce-2080-4616-8413-32558aeb2525
                Copyright © © 2011
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                http://doi.wiley.com/10.1002/tdm_license_1

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