Document Detail


Synthesis of 2-amino-8-oxodecanoic acids (Aodas) present in natural hystone deacetylase inhibitors.
MedLine Citation:
PMID:  16388624     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
[reaction: see text] Differently substituted 2-amino-8-oxodecanoic acids (Aodas), present in naturally occurring inhibitors of hystone deacetylase (HDAC), have been prepared using a convergent approach. The configuration in position 2 was derived from enantiomerically pure allylglycine or glutamic acid, whereas the stereochemistry of the substituent in position 9 derived from lactic acid or glyceraldehyde derivatives. Starting from allylglycine, (S)-Aodas, protected at the nitrogen as Boc or Fmoc, were obtained in four steps in about 30% overall yield. These products have been used to prepare a simplified analogue of a natural cyclic tetrapeptide HDAC inhibitor by SPPS.
Authors:
Manuela Rodriquez; Ines Bruno; Elena Cini; Mauro Marchetti; Maurizio Taddei; Luigi Gomez-Paloma
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  71     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2006 Jan 
Date Detail:
Created Date:  2006-01-03     Completed Date:  2006-07-26     Revised Date:  2009-11-19    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  103-7     Citation Subset:  IM    
Affiliation:
Dipartimento di Scienze Farmaceutiche, Università degli Studi di Salerno, Via Ponte don Melillo, 84084 Fisciano, Salerno, Italy.
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MeSH Terms
Descriptor/Qualifier:
Amination
Decanoic Acids / chemical synthesis,  chemistry*
Enzyme Inhibitors / chemical synthesis*,  chemistry,  pharmacology
Histone Deacetylase Inhibitors*
Molecular Structure
Oxygen / chemistry*
Peptides / chemical synthesis,  chemistry,  pharmacology
Chemical
Reg. No./Substance:
0/Decanoic Acids; 0/Enzyme Inhibitors; 0/Histone Deacetylase Inhibitors; 0/Peptides; 334-48-5/decanoic acid; 7782-44-7/Oxygen

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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