scholarly journals Syntheses and Investigations of Conformationally Restricted, Linker-Free α-Amino Acid–BODIPYs via Boron Functionalization

2021 ◽  
Author(s):  
Maodie Wang ◽  
Guanyu Zhang ◽  
Petia Bobadova-Parvanova ◽  
Kevin M. Smith ◽  
M. Graça H. Vicente
Keyword(s):  
Amino Acid ◽  
Conformationally Restricted

The conformational restriction of synthetic peptides, including a malaria peptide, for use as immunogens

1989 ◽  
Vol 323 (1217) ◽  
pp. 565-572 ◽  
Keyword(s):  
Hydrogen Bond ◽  
Plasmodium Falciparum ◽  
Amino Acid ◽  
Hydrogen Bonds ◽  
Synthetic Peptides ◽  
Synthetic Methods ◽  
Amide Hydrogen ◽  
Conformational Restriction ◽  
Conformationally Restricted ◽  
New Strategy

A new strategy is advanced for the conformational restriction of peptidyl immunogens. Our approach is to replace putative amide-amide hydrogen bonds with covalent hydrogen-bond mimics. Because on average every other amino acid in a protein engages in this bond, the syntheses of diversely shaped peptides can be contemplated. Synthetic methods for introducing a potential hydrogen-bond mimic into a peptide with α-helical potential is reported and the structural consequences are discussed. The replacement of the hydrogen bond with a chemical link will modify as well as shape the peptide. To explore the consequences of these changes, a potential synthetic vaccine for malaria, the repeating tetrapeptide Asn-Pro-Asn-Ala, was conformationally restricted. Antibodies to the shaped malarial peptide showed a strong cross reaction with Plasmodium falciparum sporozoites.

α-Amino acid Tröger base derivatives, possible conformationally restricted scaffolds?

2007 ◽  
pp. 389-391 ◽  
Author(s):  
Sean P. Bew ◽  
Laurent Legentil ◽  
Vincent Scholier ◽  
Sunil V. Sharma
Keyword(s):  
Amino Acid ◽  
Conformationally Restricted

Conformational modulation of peptides using β-amino benzenesulfonic acid (SAnt)

2015 ◽  
Vol 13 (7) ◽  
pp. 2087-2091 ◽  
Author(s):  
Gowri Priya ◽  
Amol S. Kotmale ◽  
Debamitra Chakravarty ◽  
Vedavati G. Puranik ◽  
Pattuparambil R. Rajamohanan ◽  
...  
Keyword(s):  
Amino Acid ◽  
Short Peptides ◽  
Benzenesulfonic Acid ◽  
Conformationally Restricted

This communication describes the utility of the conformationally restricted aromatic β-amino acid (2-aminobenzenesulfonic acid, SAnt) for inducing various folding interactions in short peptides.

Synthesis of Unsaturated Analogues of Glutamic Acid: Amination of Trianions From Unsaturated Dicarboxylic Acids With Chloramine

1996 ◽  
Vol 49 (7) ◽  
pp. 785 ◽  
Author(s):  
RD Allan ◽  
RK Duke ◽  
TW Hambley ◽  
GAR Johnston ◽  
KN Mewett ◽  
...  
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Double Bond ◽  
Glutamic Acid ◽  
Dicarboxylic Acid ◽  
Dicarboxylic Acids ◽  
Space Group ◽  
Conformationally Restricted ◽  
Convenient Synthesis

Trianions can be formed from dicarboxylic acids which contain a β,γ -double bond, and amination with chloramine yields β,γ-unsaturated α-amino acids. This methodology provides a convenient synthesis of amino acids that are inaccessible by other routes. (Z)-3-Phenylthiopent-2-enedioic acid and all four stable unsaturated analogues of the conformationally restricted glutamate analogue 1-aminocyclopentane-1,3-dicarboxylic acid have been synthesized to demonstrate the applicability of the method. The structure of one of the amino acid products, (�)-cis-1-aminocyclopent-4-ene-1,3-dicarboxylic acid (7), has been determined; it crystallizes in the space group P21/c, a 9.245(24), b 8.455(2), c 9.311(3) Ǻ, β 95.00(2)°, and the structure was refined to R 0.035 for 980 F.

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