| Synthesis of Carbohydrates in a Continuous Flow Reactor by Immobilized Phosphatase and Aldolase. | |
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MedLine Citation:
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PMID: 23150241 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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Herein, we report a new flow process with immobilized enzymes to synthesize complex chiral carbohydrate analogues from achiral inexpensive building blocks in a three-step cascade reaction. The first reactor contained immobilized acid phosphatase, which phosphorylated dihydroxyacetone to dihydroxyacetone phosphate using pyrophosphate as the phosphate donor. The second flow reactor contained fructose-1,6-diphosphate aldolase (RAMA, rabbit muscle aldolase) or rhamnulose-1-phosphate aldolase (RhuA from Thermotoga maritima) and acid phosphatase. The immobilized aldolases coupled the formed dihydroxyacetone phosphate to aldehydes, resulting in phosphorylated carbohydrates. A final reactor containing acid phosphatase that dephosphorylated the phosphorylated product yielded the final product. Different aldehydes were used to synthesize carbohydrates on a gram scale. To demonstrate the feasibility of the flow systems, we synthesized 0.6 g of the D-fagomine precursor. By using immobilized aldolase RhuA we were also able to obtain other stereoisomers of the D-fagomine precursor. |
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Authors:
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Lara Babich; Aloysius F Hartog; Lieke J C van Hemert; Floris P J T Rutjes; Ron Wever |
Publication Detail:
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Type: JOURNAL ARTICLE Date: 2012-11-13 |
Journal Detail:
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Title: ChemSusChem Volume: - ISSN: 1864-564X ISO Abbreviation: ChemSusChem Publication Date: 2012 Nov |
Date Detail:
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Created Date: 2012-11-14 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 101319536 Medline TA: ChemSusChem Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
Copyright Information:
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Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. |
Affiliation:
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Van 't Hoff Institute for Molecular Sciences, University of Amsterdam, Science Park 904, 1098 XH Amsterdam (The Netherlands). |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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