Effect of deuteration on the strength of the amide hydrogen bond

1972 ◽  
Vol 94 (25) ◽  
pp. 8889-8892 ◽  
Author(s):  
Gordon C. Kresheck ◽  
Daniel Kierleber ◽  
Robert J. Albers
Keyword(s):  
Hydrogen Bond ◽  
Amide Hydrogen

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.

Amide hydrogen bonding in organic medium

1980 ◽  
Vol 58 (13) ◽  
pp. 1372-1375 ◽  
Author(s):  
J. N. Spencer ◽  
Robert C. Garrett ◽  
Fred J. Mayer ◽  
Johanna E. Merkle ◽  
Carla R. Powell ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Infrared Spectroscopy ◽  
Proton Donor ◽  
Organic Medium ◽  
Association Constants ◽  
The Self ◽  
Amide Hydrogen ◽  
Theoretical Predictions ◽  
Self Association

Thermodynamic parameters for the self-association of N-methylformamide and N-methylacetamide in CCl4 solvent have been determined by infrared spectroscopy. The pure base calorimetric method was used to determine the enthalpy of hydrogen bond complex formation of N-methylformamide and N-methylacetamide with N,N-dimethylformamide, N,N-dimethylacetamide, ethyl acetate, and dioxane. Comparison of the calorimetric and spectroscopic results show that the dimers of N-methylformamide and N-methylacetamide are linear with hydrogen bond enthalpies of −2.9 and −3.9 kcal mol−1 respectively. The carbonyl group of N-methylacetamide was found to be a better proton accepter than the carbonyl of N-methylformamide in agreement with theoretical predictions. N-methylacetamide was found to be a better proton donor than N-methylformamide in disagreement with theoretical predictions. The dimer self-association constants appear to be larger than previously reported.

scholarly journals The synthesis of a pyridine-N-oxide isophthalamide rotaxane utilizing supplementary amide hydrogen bond interactions

2016 ◽  
Vol 14 (33) ◽  
pp. 7972-7981 ◽  
Author(s):  
Nicholas H. Evans ◽  
Charles E. Gell ◽  
Michael J. G. Peach
Keyword(s):  
Hydrogen Bond ◽  
Nmr Spectroscopy ◽  
Computational Modelling ◽  
Amide Hydrogen ◽  
X Ray ◽  
X Ray Crystallography ◽  
Hydrogen Bond Interactions

A pyridine-N-oxide containing rotaxane has been prepared in 32% yield. The role of macrocycle structure in successful pseudo-rotaxane formation has been rationalised by a combination of NMR spectroscopy, X-ray crystallography and computational modelling.

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