Six cyclic pseudopeptides with general formula cyclo-(L-AA-D-Oxd)n [where AA is an alpha-amino acid, D-Oxd is trans-(4R,5S) 4-carboxy-5-methyl oxazolidin-2-one and n = 3, 4] have been designed and efficiently synthesized in the liquid phase with good overall yields. The crucial step is the macrocyclization that always occurs with satisfactory yields, regardless of the cycle dimension and the presence of varying functional groups in the side chain. Moreover a dansyl (dansyl = 5-dimethylamino-1-naphthalenesulfonyl) unit was introduced in the side chain with the aim of preparing a labelled cyclopeptide that can be easily located in a biological environment.
G. Angelici, R. Tresanchez Carrera, G. Luppi, C. Tomasini (2008). The Design and Synthesis of Dansyl Containing Cyclic Pseudopeptides. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 3552-3558 [10.1002/ejoc.200800248].
The Design and Synthesis of Dansyl Containing Cyclic Pseudopeptides
ANGELICI, GAETANO;LUPPI, GIANLUIGI;TOMASINI, CLAUDIA
2008
Abstract
Six cyclic pseudopeptides with general formula cyclo-(L-AA-D-Oxd)n [where AA is an alpha-amino acid, D-Oxd is trans-(4R,5S) 4-carboxy-5-methyl oxazolidin-2-one and n = 3, 4] have been designed and efficiently synthesized in the liquid phase with good overall yields. The crucial step is the macrocyclization that always occurs with satisfactory yields, regardless of the cycle dimension and the presence of varying functional groups in the side chain. Moreover a dansyl (dansyl = 5-dimethylamino-1-naphthalenesulfonyl) unit was introduced in the side chain with the aim of preparing a labelled cyclopeptide that can be easily located in a biological environment.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
