Complestatin Synthetic Studies: The Effect of the Amino Acid Configuration on Peptide Backbone Conformation in the Common Western BCD Macrocycle.

ChemInform ◽  
2004 ◽  
Vol 35 (34) ◽  
Author(s):  
Amos B. Smith III ◽  
Jason J. Chruma ◽  
Qiang Han ◽  
Joseph Barbosa
Keyword(s):  
Amino Acid ◽  
Peptide Backbone ◽  
Backbone Conformation ◽  
The Common ◽  
Peptide Backbone Conformation ◽  
Synthetic Studies

scholarly journals Role of peptide backbone conformation on biological activity of chemotactic peptides.

1991 ◽  
Vol 266 (28) ◽  
pp. 18460-18468
Author(s):  
A.R. Dentino ◽  
P.A. Raj ◽  
K.K. Bhandary ◽  
M.E. Wilson ◽  
M.J. Levine
Keyword(s):  
Biological Activity ◽  
Peptide Backbone ◽  
Backbone Conformation ◽  
Chemotactic Peptides ◽  
Peptide Backbone Conformation

Peptide Backbone Conformation Affects the Substrate Preference of Protein Arginine Methyltransferase I

Biochemistry ◽  
2012 ◽  
Vol 51 (27) ◽  
pp. 5463-5475 ◽  
Author(s):  
Knut Kölbel ◽  
Christian Ihling ◽  
Uwe Kühn ◽  
Ines Neundorf ◽  
Silke Otto ◽  
...  
Keyword(s):  
Substrate Preference ◽  
Protein Arginine Methyltransferase ◽  
Peptide Backbone ◽  
Arginine Methyltransferase ◽  
Backbone Conformation ◽  
Peptide Backbone Conformation

Modulation of the Peptide Backbone Conformation by the Selenoxo Photoswitch

2010 ◽  
Vol 132 (22) ◽  
pp. 7578-7579 ◽  
Author(s):  
Yun Huang ◽  
Günther Jahreis ◽  
Christian Lücke ◽  
Dirk Wildemann ◽  
Gunter Fischer
Keyword(s):  
Peptide Backbone ◽  
Backbone Conformation ◽  
Peptide Backbone Conformation

scholarly journals Hybrid Cyclobutane/Proline-Containing Peptidomimetics: The Conformational Constraint Influences Their Cell-Penetration Ability

2021 ◽  
Vol 22 (10) ◽  
pp. 5092
Author(s):  
Ona Illa ◽  
Jimena Ospina ◽  
José-Emilio Sánchez-Aparicio ◽  
Ximena Pulido ◽  
María Ángeles Abengozar ◽  
...  
Keyword(s):  
Amino Acid ◽  
Cell Penetrating Peptides ◽  
Cell Uptake ◽  
Relevant Parameter ◽  
Intracellular Accumulation ◽  
Peptide Backbone ◽  
New Family ◽  
Cell Line Hela ◽  
Penetration Ability ◽  
Tumoral Cell

A new family of hybrid β,γ-peptidomimetics consisting of a repetitive unit formed by a chiral cyclobutane-containing trans-β-amino acid plus a Nα-functionalized trans-γ-amino-l-proline joined in alternation were synthesized and evaluated as cell penetrating peptides (CPP). They lack toxicity on the human tumoral cell line HeLa, with an almost negligible cell uptake. The dodecapeptide showed a substantial microbicidal activity on Leishmania parasites at 50 µM but with a modest intracellular accumulation. Their previously published γ,γ-homologues, with a cyclobutane γ-amino acid, showed a well-defined secondary structure with an average inter-guanidinium distance of 8–10 Å, a higher leishmanicidal activity as well as a significant intracellular accumulation. The presence of a very rigid cyclobutane β-amino acid in the peptide backbone precludes the acquisition of a defined conformation suitable for their cell uptake ability. Our results unveiled the preorganized charge-display as a relevant parameter, additional to the separation among the charged groups as previously described. The data herein reinforce the relevance of these descriptors in the design of CPPs with improved properties.

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