160219-64-7Relevant academic research and scientific papers
Complestatin to chloropeptin I via a quantitative acid catalyzed rearrangement. Absolute stereochemical determination of complestatin
Jayasuriya, Hiranthi,Salituro, Gino M.,Smith, Scott K.,Heck, James V.,Gould, Steven J.,Singh, Sheo B.,Homnick, Carl F.,Holloway, M. Katharine,Pitzenberger, Steven M.,Patane, Michael A.
, p. 2247 - 2248 (1998)
Complestatin and isomeric chloropeptin I are bicyclo hexapeptides isolated from a Streptomyces sp. Both of these compounds are inhibitors of gp120-CD4 HIV fusion activity. In this paper, we describe an efficient acid catalyzed conversion of complestatin t
The complestatins as HIV-1 integrase inhibitors. Efficient isolation, structure elucidation, and inhibitory activities of isocomplestatin, chloropeptin I, new complestatins, A and B, and acid-hydrolysis products of chloropeptin I
Singh,Jayasuriya,Salituro,Zink,Shafiee,Heimbuch,Silverman,Lingham,Genilloud,Teran,Vilella,Felock,Hazuda
, p. 874 - 882 (2001)
From the screening of a microbial extract library, isocomplestatin (1), a new axial-chiral isomer of complestatin (2) which is a known rigid bicyclic hexapeptide, was identified as a potent natural product inhibitor of HIV-1 integrase, a unique enzyme responsible for viral replication. Isocomplestatin showed inhibitory activities (IC50) in coupled 3′-end processing/strand transfer (200 nM), strand transfer (4 μM), and HIV-1 replication (200 nM) in virus-infected cells. Attempted large-scale isolation of 1 by the literature method, used for the isolation of complestatin, led to lower yield and limited availability. We have developed several new, two-step, high-yielding absorption/elution methods of isolation based on reverse-phase chromatography at pH 8 that are applicable to scales from one gram to potential industrial quantities. We have also discovered and determined the structure of two new congeners of 1, namely, complestatins A (4) and B (5), with almost equal HIV-1 integrase activity. They differ from 1 at C2′ and C3′ of the tryptophan moiety (residue F). Selective acid hydrolysis of chloropeptin I (3), itself a known acid-catalyzed rearranged isomer of 1 and 2 (8′- vs 7′-substitution in tryptophan residue F, respectively), an isomer of complestatin, and isocomplestatin resulted in a number of fragments (6-10) with retention of most of the HIV-1 integrase activity. The structure - activity relationship as revealed by these compounds could possibly lead to the design of better inhibitors or understanding of the HIV-1 integrase target.
Total synthesis of chloropeptin II (complestatin) and chloropeptin I
Garfunkle, Joie,Kimball, F. Scott,Trzupek, John D.,Takizawa, Shinobu,Shimamura, Hiroyuki,Tomishima, Masaki,Boger, Dale L.
supporting information; experimental part, p. 16036 - 16038 (2010/02/15)
(Chemical Equation Presented) The first total synthesis of chloropeptin II (1, complestatin) is disclosed. Key elements of the approach include the use of an intramolecular Larock indole synthesis for the initial macrocyclization, adopting conditions that
Total synthesis of anti-HIV agent chloropeptin I
Deng, Hongbo,Jung, Jae-Kyung,Liu, Tao,Kuntz, Kevin W.,Snapper, Marc L.,Hoveyda, Amir H.
, p. 9032 - 9034 (2007/10/03)
A convergent diastereo- and enantioselective total synthesis of anti-HIV agent chloropeptin I is reported. Important features of the total synthesis include: (1) the use of Ti-catalyzed cyanide addition to imines to prepare a requisite amino acid moiety,
