1177451-86-3Relevant academic research and scientific papers
Total synthesis, characterization, and conformational analysis of the naturally occurring hexadecapeptide integramide A and a diastereomer
De Zotti, Marta,Damato, Francesca,Formaggio, Fernando,Crisma, Marco,Schievano, Elisabetta,Mammi, Stefano,Kaptein, Bernard,Broxterman, Quirinus B.,Felock, Peter J.,Hazuda, Daria J.,Singh, Sheo B.,Kirschbaum, Jochen,Brueckner, Hans,Toniolo, Claudio
scheme or table, p. 316 - 327 (2010/04/02)
Integramide A is a 16-amino acid peptide inhibitor of the enzyme HIV-1 integrase. We have recently reported that the absolute stereochemistries of the dipeptide sequence near the C terminus are L-Iva14-D-Iva 15. Herein, we describe the syntheses of the natural compound and its D-Iva14-L-Iva15 diastereomer, and the results of their chromatographic/mass spectrometry analyses. We present the conformational analysis of the two compounds and some of their synthetic in-termediates of different main-chain length in the crystal state (by X-ray diffraction) and in solvents of different polarities (using circular dichroism, FTIR absorption, and 2D NMR techniques), These data shed light on the mechanism of inhibition of HIV-1 integrase, which is an important target for anti-HIV therapy.
