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Plausible origins of homochirality in the amino acid catalyzed neogenesis of carbohydrates
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
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2005 (English)In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 2005, 2047-2049 p.Article in journal (Refereed) Published
Abstract [en]

The intrinsic ability of amino acids to catalyze the asymmetric formation of carbohydrates, which enzymes have mediated for millions of years, with significant amplification of enantiomeric excess suggests a plausible ancient catalytic process for the evolution of homochirality.

Place, publisher, year, edition, pages
2005. Vol. 2005, 2047-2049 p.
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-23700DOI: 10.1039/b500589bOAI: oai:DiVA.org:su-23700DiVA: diva2:194027
Note
Part of urn:nbn:se:su:diva-449Available from: 2005-04-07 Created: 2005-04-07 Last updated: 2017-12-13Bibliographically approved
In thesis
1. Direct Amino Acid-Catalyzed Enantioselective α-Oxidation Reactions and Asymmetric de novo Synthesis of Carbohydrates
Open this publication in new window or tab >>Direct Amino Acid-Catalyzed Enantioselective α-Oxidation Reactions and Asymmetric de novo Synthesis of Carbohydrates
2005 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

The ability of amino acids to form nucleophilic enamines with aldehydes and ketones has been used in the development of asymmetric α-oxidation reactions with electrophilic oxidizing agents. Singlet molecular oxygen has for the first time been asymmetrically incorporated into aldehydes and ketones, and the products were isolated as their corresponding diols in good yields and ee’s. Organocatalytic α-oxidations of cyclic ketones with iodosobenzene and N-sulfonyloxaziridine were also possible and furnished after reduction the product diols in generally low yields and in low to good ee’s. Amino acids have also been shown to catalyze the formation of carbohydrates by sequential aldol reactions. For example, proline and hydroxy proline mediate a highly selective trimerisation of α-benzyloxyacetaldehyde into allose, which was obtained in >99 % ee. Non linear effect studies of this reaction revealed the largest permanent nonlinear effect observed in a proline-catalyzed reaction to date. Moreover, polyketides were also assembled in a similar fashion by an amino acid-catalyzed one-pot reaction, and was successful for the trimerisation of propionaldehyde, however the sequential cross aldol reactions suffered from lower selectivities. This problem was overcome by the development of a two-step synthesis that enabled the formation of a range of polyketides with excellent selectivities from a variety of aldehydes. The method furnishes the polyketides via the shortest route reported and in comparable product yields to most multi-step synthesis. All polyketides were isolated as single diastereomers with >99 % ee. Based on the observed amino acid-catalysis, amino acids are thought to have taken part in the prebiotic formation of tetroses and hexoses.

Place, publisher, year, edition, pages
Stockholm: Institutionen för organisk kemi, 2005
Keyword
Organo catalysis
National Category
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-449 (URN)91-7155-035-6 (ISBN)
Public defence
2005-04-28, sal G, Arrheniuslaboratorierna, Svante Arrhenius väg 14-18, Stockholm, 10:00
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Available from: 2005-04-07 Created: 2005-04-07Bibliographically approved

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