That elusive chiral pair: The chiral sequence of the nonribosomal, linear, 16-mer peptide integramide A, an HIV-1 integrase A inhibitor, has been fully elucidated. Total independent chemical syntheses of two diastereomers of integramide A (L-Iva14-D-Iva15 and D-Iva14-L-Iva15) in the solution phase, combined with their HPLC and 1D- and 2D-NMR analyses, provide unambiguous evidence that the natural inhibitor has a previously unassigned L-Iva14-D-Iva15 chiral pair.
Complete Absolute Configuration of Integramide A, a Natural, 16-mer Peptide Inhibitor of HIV-1 Integrase, Elucidated by Total Synthesis
DE ZOTTI, MARTA;FORMAGGIO, FERNANDO;TONIOLO, CLAUDIO
2009
Abstract
That elusive chiral pair: The chiral sequence of the nonribosomal, linear, 16-mer peptide integramide A, an HIV-1 integrase A inhibitor, has been fully elucidated. Total independent chemical syntheses of two diastereomers of integramide A (L-Iva14-D-Iva15 and D-Iva14-L-Iva15) in the solution phase, combined with their HPLC and 1D- and 2D-NMR analyses, provide unambiguous evidence that the natural inhibitor has a previously unassigned L-Iva14-D-Iva15 chiral pair.
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