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Complete Absolute Configuration of Integramide A, a Natural, 16‐mer Peptide Inhibitor of HIV‐1 Integrase, Elucidated by Total Synthesis
Author(s) -
De Zotti Marta,
Formaggio Fernando,
Kaptein Bernard,
Broxterman Quirinus B.,
Felock Peter J.,
Hazuda Daria J.,
Singh Sheo B.,
Brückner Hans,
Toniolo Claudio
Publication year - 2009
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.200800443
Subject(s) - integrase , diastereomer , stereochemistry , chemistry , human immunodeficiency virus (hiv) , absolute configuration , integrase inhibitor , nonribosomal peptide , total synthesis , peptide , sequence (biology) , combinatorial chemistry , enzyme , antiretroviral therapy , virology , biochemistry , biology , biosynthesis , viral load
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.