http://www.cnr.it/ontology/cnr/individuo/prodotto/ID16078

Total synthesis, characterization, and conformational analysis of the naturally occurring hexadecapeptide Integramide A and a diastereomer (Articolo in rivista)

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Total synthesis, characterization, and conformational analysis of the naturally occurring hexadecapeptide Integramide A and a diastereomer (Articolo in rivista) (literal)

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Alternative label

Marta De Zotti; Francesca Damato; Fernando Formaggio; Marco Crisma; Elisabetta Schievano; Stefano Mammi; Bernard Kaptein; Quirinus B. Broxterman; Peter J. Felock; Daria J. Hazuda; Sheo B. Singh; Jochen Kirschbaum; Hans Brückner; ClaudioToniolo (2010)
Total synthesis, characterization, and conformational analysis of the naturally occurring hexadecapeptide Integramide A and a diastereomer
in Chemistry - A European Journal
(literal)

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Marta De Zotti; Francesca Damato; Fernando Formaggio; Marco Crisma; Elisabetta Schievano; Stefano Mammi; Bernard Kaptein; Quirinus B. Broxterman; Peter J. Felock; Daria J. Hazuda; Sheo B. Singh; Jochen Kirschbaum; Hans Brückner; ClaudioToniolo (literal)

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Institute of Biomolecular Chemistry, CNR, Padova Unit, Department of Chemistry University of Padova, via Marzolo 1, 35131 Padova (Italy); DSM Pharmaceutical Products, Innovative Synthesis and Catalysis, P.O. Box 18, 6160 MD Geleen (The Netherlands); 9,10,11: Merck Research Laboratories, Rahway NJ 07065 and West Point, PA 19486 (USA); Department of Food Sciences, Interdisciplinary Research Centre for Biosystems, Land Use and Nutrition, University of Giessen, 35392 Giessen (Germany) (literal)

Titolo

Total synthesis, characterization, and conformational analysis of the naturally occurring hexadecapeptide Integramide A and a diastereomer (literal)

Abstract

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-Iva15. Herein, we describe the syntheses of the natural compound and its D-Iva14-L-Iva15 diastereomer, and the results of their chromatographic/mass spectrometric analyses. We present the conformational analysis of the two compounds and some of their synthetic intermediates 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. (literal)

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