Complete Absolute Configuration of Integramide A, a Natural, 16‐mer Peptide Inhibitor of HIV‐1 Integrase, Elucidated by Total Synthesis | Zendy

De Zotti Marta | Zendy; Formaggio Fernando | Zendy; Kaptein Bernard | Zendy; Broxterman Quirinus B. | Zendy; Felock Peter J. | Zendy; Hazuda Daria J. | Zendy; Singh Sheo B. | Zendy; Brückner Hans | Zendy; Toniolo Claudio | Zendy

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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.

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