| Chemoenzymatic synthesis of differentially protected 3-deoxysugars. | |
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MedLine Citation:
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PMID: 21124399 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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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Authors:
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Dennis G Gillingham; Pierre Stallforth; Alexander Adibekian; Peter H Seeberger; Donald Hilvert |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't Date: 2010-01-17 |
Journal Detail:
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Title: Nature chemistry Volume: 2 ISSN: 1755-4349 ISO Abbreviation: Nat Chem Publication Date: 2010 Feb |
Date Detail:
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Created Date: 2010-12-02 Completed Date: 2011-01-06 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 101499734 Medline TA: Nat Chem Country: England |
Other Details:
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Languages: eng Pagination: 102-5 Citation Subset: IM |
Affiliation:
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Laboratory of Organic Chemistry, ETH Zurich, 8093 Zurich, Switzerland. |
| Data Bank Information | |
Bank Name/Acc. No.:
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PubChem-Substance/85845735; 85845736; 85845737; 85845738; 85845739; 85845740; 85845741; 85845742; 85845743; 85845744; 85845745; 85845746; 85845747; 85845748; 85845749; 85845750; 85845751; 85845752; 85845753; 85845754; 85845755; 85845756; 85845757; 85845758; 85845759; 85845760; 85845761; 85845762; 85845763; 85845764; 85845765; 85845766; 85845767; 85845768 |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Biocatalysis Carbohydrates / biosynthesis*, chemistry* Catalytic Domain Models, Molecular Multienzyme Complexes / chemistry, metabolism* Pyruvates / metabolism Stereoisomerism Substrate Specificity |
| Chemical | |
Reg. No./Substance:
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0/Carbohydrates; 0/Multienzyme Complexes; 0/Pyruvates; 0/macrophomate synthase |
| Comments/Corrections | |
Comment In:
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Nat Chem. 2010 Feb;2(2):85-6
[PMID:
21124396
]
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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