16. Aldolases as Catalyst for the Synthesis of Carbohydrates and Analogs

  1. Sergio Riva2 and
  2. Wolf-Dieter Fessner3
  1. Pere Clapés,
  2. Jesús Joglar and
  3. Jordi Bujons

Published Online: 27 JUN 2014

DOI: 10.1002/9783527682492.ch16

Cascade Biocatalysis : Integrating Stereoselective and Environmentally Friendly Reactions

Cascade Biocatalysis : Integrating Stereoselective and Environmentally Friendly Reactions

How to Cite

Clapés, P., Joglar, J. and Bujons, J. (2014) Aldolases as Catalyst for the Synthesis of Carbohydrates and Analogs, in Cascade Biocatalysis : Integrating Stereoselective and Environmentally Friendly Reactions (eds S. Riva and W.-D. Fessner), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany. doi: 10.1002/9783527682492.ch16

Editor Information

  1. 2

    Istituto di Chimica del, Riconoscimento Molecolare, C. N. R., Via Mario Bianco 9, 20131 Milano, Italy

  2. 3

    Technische Universität, Darmstadt, Department of Organic, Chemistry and Biochemistry, Petersenstr. 22, D-64287 Darmstadt, Germany

Author Information

  1. Instituto de Química Avanzada de Cataluña IQAC-CSIC, Dept Chemical Biology and Molecular Modeling, Biotransformation and Bioactive Molecules Group, Jordi Girona 18-26, 08034, Barcelona, Spain

Publication History

  1. Published Online: 27 JUN 2014
  2. Published Print: 23 JUL 2014

ISBN Information

Print ISBN: 9783527335220

Online ISBN: 9783527682492

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Keywords:

  • Carboligation;
  • stereoselectivity;
  • aldolase;
  • mutagenesis;
  • carbohydrate;
  • iminocyclitols

Summary

Carbon-carbon bond formation catalyzed by carboligases is finding undeniable increasing acceptance in chemical research and laboratory as well as in large-scale production of polyhydroxylated complex molecules. Aldolases, being highly selective and efficient, offer a green tool to perform asymmetric carbon-carbon bond formation independently or in cascade or multistep reactions in combination with other enzymes in a sustainable, environmentally benign fashion. In this chapter, an account on the latest research about chemoenzymatic multistep strategies to the synthesis of iminocyclitols, carbohydrates and deoxysugars from N-protected-aminoaldehydes, hydroxyaldehydes, and simple alkylaldehydes, respectively is presented. The key step in those processes is the stereoselective aldol addition reaction of dihydroxyacetone phosphate (DHAP) and/or their unphosphorylated analogues to the acceptor aldehydes using DHAP-dependent and DHA using aldolases, respectively as biocatalysts.