Regioselective structural and functional mimicry of peptides. Design of hydrolytically-stable cyclic peptidomimetic inhibitors of HIV-1 protease.

Abbenante, Giovanni; March, Darren R.; Bergman, Douglas A.; Hunt, Philip A.; Garnham, B.; Dancer, Robert J.; Martin, Jennifer L.; Fairlie, David P.

doi:10.1021/ja00146a007

Cited by 54 publications

(66 citation statements)

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“…During her PhD she studied the influence of the stereochemistry and incorporated heterocycles on the Cu II table from L. patella and L. bistratum have attracted scientific interest for more than two decades, as they provide a wide range of cyclic peptides, based on unusual amino acids and with unusual structures and properties. [8][9][10][11][12][13][14][15][16]19 Ascidians harbor an obligate symbiont, Prochloron sp., which, it is thought, might produce the cyclic peptides. 20,21 Through photosynthesis, Prochloron is an extremely important nutrient for their hosts.…”

Section: Nina Dovalilmentioning

confidence: 99%

Cyclic peptide marine metabolites and Cu^II

et al. 2014

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a Cyclic pseudo-peptides derived from marine metabolites of the genus Lissoclinum bistratum and Lissoclinum patella have attracted scientific interest in the last two decades. Their structural properties and solution dynamics have been analyzed in detail, elaborate synthetic procedures for the natural products and synthetic derivatives developed, the biosynthetic pathways studied and it now is possible to produce them biosynthetically. Initially, these macrocyclic ligands were studied due to their medicinal and pharmaceutical potential -some of the isolated cyclic pseudo-peptides show high cytotoxic and antiviral activity.A major focus in the last decade has been on their Cu II coordination chemistry, as a number of studies have indicated that dinuclear Cu II complexes of cyclic peptides may be involved in the ascidians' metabolism, and this is the focus of the present review.

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Section: Nina Dovalilmentioning

confidence: 99%

Cyclic peptide marine metabolites and Cu^II

et al. 2014

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“…Spectroscopic data are in agreement with previous publications. [5,6] (b) To a racemic solution of 1 (2 mmol) in toluene (3 mL) and THF (8 mL) at 2308C, the corresponding dipeptide, previously synthesized and protected as ester (2 mmol) and solubilized in the minimal THF amount, was added dropwise. The mixture was stirred for 15 min.…”

Section: Peptidosulfonamides 861mentioning

confidence: 99%

New Mild and Efficient Synthesis of Peptidosulfonamides

Papandrea

Ponticelli

2008

Synthetic Communications

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“…The HIV protease substrates AcSer-Leu-Asn-Phe-Pro-Ile-Val and Ac-Leu-Val-Phe-Phe-IleVal-NH 2 were easily converted to potent competitive inhibitors by replacing the scissile amide bond (-CONH-) with non-cleavable transition state isosteres (i.e. -CHOH-CH 2 -) [150]. On the base of the X-ray structure of these derivatives bound to HIVPR, Fairlie's group designed several 15 and 16 member macrocycles by linking together the side chains of the first and third amino acids, flanking either the left or the right side of the scissile amide bond [150,151].…”

Section: β-Strand Mimetics As Protease Inhibitorsmentioning

confidence: 99%

“…-CHOH-CH 2 -) [150]. On the base of the X-ray structure of these derivatives bound to HIVPR, Fairlie's group designed several 15 and 16 member macrocycles by linking together the side chains of the first and third amino acids, flanking either the left or the right side of the scissile amide bond [150,151]. The resulting C-and N-terminal macrocyclic derivatives [48 (IC 50 = 12 nM) and 49 (IC 50 = 0.6 nM), Fig.…”

Section: β-Strand Mimetics As Protease Inhibitorsmentioning

confidence: 99%

Modulation of Protein-Protein Interactions by Stabilizing/Mimicking Protein Secondary Structure Elements

Vega

Martı́n-Martı́nez²,

González‐Muñiz

2007

CTMC

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In view of the crucial role of protein-protein intercommunication both in biological and pathological processes, the search of modulators of protein-protein interactions (PPIs) is currently a challenging issue. The development of rational strategies to imitate key secondary structure elements of protein interfaces is complementary to other approaches based on the screening of synthetic or virtual libraries. In this sense, the present review provides representative examples of compounds that are able to disturb PPIs of therapeutic relevance, through the stabilization or the imitation of peptide hot-spots detected in contact areas of the interacting proteins. The review is divided into three sections, covering mimetics of the three main secondary structural elements found in proteins, in general, and in protein-protein interfaces, in particular (alpha-helices, beta-sheets, and reverse turns). Once the secondary element has been identified, the first approach typically involves the translation of the primary peptide structure into different cyclic analogues. This is normally followed by gradual decrease of the peptide nature through combination of peptide and non-peptide fragments in the same molecule. The final step usually consists in the development of pertinent organic scaffolds for appending key functional groups in the right spatial disposition, as a means towards totally non-peptide small molecule PPI modulators.

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Regioselective structural and functional mimicry of peptides. Design of hydrolytically-stable cyclic peptidomimetic inhibitors of HIV-1 protease.

Cited by 54 publications

References 0 publications

Cyclic peptide marine metabolites and Cu^II

Cyclic peptide marine metabolites and Cu^II

New Mild and Efficient Synthesis of Peptidosulfonamides

Modulation of Protein-Protein Interactions by Stabilizing/Mimicking Protein Secondary Structure Elements

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Regioselective structural and functional mimicry of peptides. Design of hydrolytically-stable cyclic peptidomimetic inhibitors of HIV-1 protease.

Cited by 54 publications

References 0 publications

Cyclic peptide marine metabolites and CuII

Cyclic peptide marine metabolites and CuII

New Mild and Efficient Synthesis of Peptidosulfonamides

Modulation of Protein-Protein Interactions by Stabilizing/Mimicking Protein Secondary Structure Elements

Contact Info

Product

Resources

About

Cyclic peptide marine metabolites and Cu^II

Cyclic peptide marine metabolites and Cu^II