Conformational Preferences of Peptides Containing Reverse-Turn Mimetic Bicyclic Lactams: Inverse γ-Turns versus Type-II′ β-Turns – Insights into β-Hairpin Stability

Belvisi, Laura; Gennari, Cesare; Mielgo, Antonia; Potenza, Donatella; Scolastico, Carlo

doi:10.1002/(sici)1099-0690(199902)1999:2<389::aid-ejoc389>3.0.co;2-7

Cited by 109 publications

(76 citation statements)

References 65 publications

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“…Complete 1 H NMR assignment of peptides I-V were obtained using a combination of 2D COSY and ROESY methods in CDCl 3 . In order to investigate the existence of intramolecular hydrogen bonding and peptide conformation in solution phase, the solvent dependence of the NH chemical shifts were examined by NMR titration [33]. In this experiment a solution of the peptide in nonpolar CDCl 3 (10 mM in 0.5 ml) was gradually titrated against polar (CD 3 ) 2 SO.…”

Section: Solution Conformational Analysismentioning

confidence: 99%

Conformational studies of γ-turn in pseudopeptides containing α-amino acid and conformationally constrained meta amino benzoic acid/meta nitro aniline

Konar

2013

Journal of Molecular Structure

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Section: Solution Conformational Analysismentioning

confidence: 99%

Conformational studies of γ-turn in pseudopeptides containing α-amino acid and conformationally constrained meta amino benzoic acid/meta nitro aniline

Konar

2013

Journal of Molecular Structure

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“…17 On the contrary, the C-terminal CONH 2 or CONHR amide protons showed chemical shifts in the range of 5.27-6.82 ppm in CDCl 3 , while the change of solvent resulted in an important fluctuation of d values, indicative of solvent exposure (normally >1 ppm, see Table 1S, Supplementary data).…”

Section: Conformational Analysis By 1 H Nmrmentioning

confidence: 99%

Synthesis and SAR studies on azetidine-containing dipeptides as HCMV inhibitors

Perez‐Faginas¹,

Aranda²,

García-López³

et al. 2011

Bioorganic & Medicinal Chemistry

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SAR studies on an azetidine-containing dipeptide prototype inhibitor of HCMV are described. Three series of structurally modified analogues, involving substitutions at the N- and C-terminus, and at the C-terminal side-chain were synthesized and evaluated for antiviral activity. Aliphatic or no substituents at the C-carboxamide group, an aliphatic C-terminal side-chain, as well as a benzyloxycarbonyl moiety at the N-terminus were absolute requirements for anti-HCMV activity. The conformational restriction induced by the 2-azetidine residue into the dipeptide derivatives, identified by (1)H NMR as a γ-type reverse turn, seems to have influence on the activity of these molecules.

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“…Detailed conformational analysis by nuclear magnetic resonance, infrared, and molecular modeling techniques [67], as well as applications as thrombin inhibitors [68], and in RGD-based cyclopeptides such as a v b 3 -integrin ligands [69], proved this class of compounds to act as d-amino acid reverse turn mimetics.…”

Section: D-amino Acids As Reverse Turn Mimeticsmentioning

confidence: 99%

Synthesis of γ‐ and δ‐Amino Acids

Trabocchi

Menchi

Guarna

2009

Amino Acids, Peptides and Proteins in Organic Chemistry

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An area of significant importance that provides new dimensions to the field of molecular diversity and drug discovery is the area of peptidomimetics [1]. Biomedical research has reoriented towards the development of new drugs based on peptides and proteins, by introducing both structural and functional specific modifications, and maintaining the features responsible for biological activity. As a part of this research area, unnatural amino acids are of valuable interest in drug discovery and their use as new building blocks for the development of peptidomimetics with a high structural diversity level is of key interest. In particular, medicinal chemistry has taken advantage of the use of amino acid homologs to introduce elements of diversity for the generation of new molecules as drug candidates in the so-called peptidomimetic approach, where a peptide lead is processed into a new nonpeptidic molecule. The additional methylenic unit between the N-and C-termini in b-amino acids results in an increase of the molecular diversity in terms of the higher number of stereoisomers and functional group variety, and many synthetic approaches to the creation of b-amino acids have been published. There is great interest in these as a tool for medicinal chemistry [2] and in the field of b-peptides generally [3]. The g-and d-amino acids have garnered similar interest. In particular, the folding properties of g-[4] and d-peptides [5] have been investigated, as they have been proved to generate stable secondary structures. The homologation of a-amino acids into g-and d-units allows an enormous increase of the chemical diversity within the three and four atoms between the amino and carboxyl groups. Thus, additional substituents and stereocenters expand the number of compounds belonging to the class of g-and d-amino acids. g-Amino acids have been reported both in linear form, and with the amino and carboxyl groups separated or incorporated in a cyclic structure. In the case of d-amino acids, five-and six-membered rings have been mainly reported having two substituents variously tethered between the amino and carboxyl groups. Moreover, bicyclic and spiro compounds have been reported as constrained d-amino acids, especially in the field of peptidomimetics. The synthetic approaches for the preparation of

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Conformational Preferences of Peptides Containing Reverse-Turn Mimetic Bicyclic Lactams: Inverse γ-Turns versus Type-II′ β-Turns – Insights into β-Hairpin Stability

Cited by 109 publications

References 65 publications

Conformational studies of γ-turn in pseudopeptides containing α-amino acid and conformationally constrained meta amino benzoic acid/meta nitro aniline

Conformational studies of γ-turn in pseudopeptides containing α-amino acid and conformationally constrained meta amino benzoic acid/meta nitro aniline

Synthesis and SAR studies on azetidine-containing dipeptides as HCMV inhibitors

Synthesis of γ‐ and δ‐Amino Acids

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