Document Detail

'Five at one stroke': proline and small peptides in the stereoselective de novo synthesis and enantiotopic functionalization of carbohydrates.
MedLine Citation:
PMID:  17193175     Owner:  NLM     Status:  MEDLINE    
Asymmetric catalysis with the simple amino acid proline (so called 'enamine catalysis') arrested big attention in the last few years since the re-discovery of the Hajos-Parrish-Eder-Sauer-Wiechert reaction. After basic mechanistic studies, probing scope and limitations of the catalyst and the corresponding reactions, this concept has now emerged to a state where it is applied to the assembly of up to five stereogenic centers of carbohydrates, not really 'at one stroke', but in only two simple synthetic operations. Beyond, it is not only possible to build up complicated natural products elegantly, but also to address selectively the similar functional groups of carbohydrates by small peptidic catalysts. This short review covers the recent developments of organocatalysis in both fields, with special emphasis on the asymmetric assembly and selective derivatization of carbohydrates.
Michael Limbach
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't; Review    
Journal Detail:
Title:  Chemistry & biodiversity     Volume:  2     ISSN:  1612-1880     ISO Abbreviation:  Chem. Biodivers.     Publication Date:  2005 Jul 
Date Detail:
Created Date:  2006-12-28     Completed Date:  2007-02-08     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101197449     Medline TA:  Chem Biodivers     Country:  Switzerland    
Other Details:
Languages:  eng     Pagination:  825-36     Citation Subset:  IM    
Laboratorium für Organische Chemie, Department Chemie und Angewandte Biowissenschaften, Eidgenössische Technische Hochschule, ETH Hönggerberg, HCI, Wolfgang-Pauli-Strasse 10, CH-8093 Zürich.
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MeSH Terms
Carbohydrates / chemical synthesis*,  chemistry*
Peptides / chemistry*
Proline / chemistry*
Reg. No./Substance:
0/Carbohydrates; 0/Peptides; 147-85-3/Proline

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