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  Chemoenzymatic synthesis of differentially protected 3-deoxysugars

Gillingham, D. G., Stallforth, P., Adibekian, A., Seeberger, P. H., & Hilvert, D. (2010). Chemoenzymatic synthesis of differentially protected 3-deoxysugars. Nature Chemistry, 2(2), 102-105. doi:10.1038/nchem.504.

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Item Permalink: http://hdl.handle.net/21.11116/0000-0006-DD65-0 Version Permalink: http://hdl.handle.net/21.11116/0000-0006-DD66-F
Genre: Journal Article

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Gillingham, Dennis G., Author
Stallforth, Pierre1, Author              
Adibekian, Alexander, Author
Seeberger, Peter H.2, Author              
Hilvert, Donald, Author
Affiliations:
1Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_1863286              
2Peter H. Seeberger, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_2040285              

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 Abstract: 3-Deoxysugars are important constituents of complex carbohydrates. For example, 2-keto-3-deoxy-D-manno-octulosonic acid (KDO) is an essential component of lipopolysaccharides in Gram-negative bacteria, 2-keto-3-deoxy-D-glycero-D-galacto-nonulosonic acid (KDN) is widely found in carbohydrates of the bacterial cell wall and in lower vertebrates, and sialic acid is a common cap of mammalian glycoproteins. Although ready access to such sugars would benefit the creation of vaccine candidates, antibiotics and small-molecule drugs, their chemical synthesis is difficult. Here we present a simple chemoenzymatic method for preparing differentially protected 3-deoxysugar derivatives from readily available starting materials. It exploits the promiscuous aldolase activity of the enzyme macrophomate synthase (MPS) to add pyruvate enolate diastereoselectively to a wide range of structurally complex aldehydes. A short synthesis of KDN illustrates the utility of this approach. Enzyme promiscuity, which putatively fosters large functional leaps in natural evolution, has great promise as a source of synthetically useful catalytic transformations.

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 Dates: 2010
 Publication Status: Published in print
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 Identifiers: DOI: 10.1038/nchem.504
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Title: Nature Chemistry
  Abbreviation : Nat. Chem.
Source Genre: Journal
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Publ. Info: London, UK : Nature Publishing Group
Pages: - Volume / Issue: 2 (2) Sequence Number: - Start / End Page: 102 - 105 Identifier: ISSN: 1755-4330