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. © 2006 American Chemical Society.

Rodriquez, M., Bruno, I., Cini, E., Marchetti, M., Taddei, M., Gomez Paloma, L. (2006). Synthesis of 2-amino-8-oxadecanoic acids (Aodas) present in nautural hystone deacetylase inhybitors. JOURNAL OF ORGANIC CHEMISTRY, 71(1), 103-107 [10.1021/jo0518250].

Synthesis of 2-amino-8-oxadecanoic acids (Aodas) present in nautural hystone deacetylase inhybitors

Cini, Elena;Taddei, Maurizio;
2006-01-01

Abstract

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. © 2006 American Chemical Society.
2006
Rodriquez, M., Bruno, I., Cini, E., Marchetti, M., Taddei, M., Gomez Paloma, L. (2006). Synthesis of 2-amino-8-oxadecanoic acids (Aodas) present in nautural hystone deacetylase inhybitors. JOURNAL OF ORGANIC CHEMISTRY, 71(1), 103-107 [10.1021/jo0518250].
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11365/9237
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