| Synthesis of 2-amino-8-oxodecanoic acids (Aodas) present in natural hystone deacetylase inhibitors. | |
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MedLine Citation:
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PMID: 16388624 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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[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. |
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Authors:
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Manuela Rodriquez; Ines Bruno; Elena Cini; Mauro Marchetti; Maurizio Taddei; Luigi Gomez-Paloma |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 71 ISSN: 0022-3263 ISO Abbreviation: J. Org. Chem. Publication Date: 2006 Jan |
Date Detail:
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Created Date: 2006-01-03 Completed Date: 2006-07-26 Revised Date: 2009-11-19 |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 103-7 Citation Subset: IM |
Affiliation:
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Dipartimento di Scienze Farmaceutiche, Università degli Studi di Salerno, Via Ponte don Melillo, 84084 Fisciano, Salerno, Italy. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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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:
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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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