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Synthesis and conformational study of model peptides containing N-substituted 3-aminoazetidine-3-carboxylic acids

(2014) EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 2014(11). p.2312-2321
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Abstract
Model peptides containing N-substituted 3-aminoazetidine-3-carboxylic acids have been synthesized to investigate the conformational features of these C-tetrasubstituted amino acids. The target peptides were designed and prepared by classical synthetic methods in solution, exploiting the convenient N-substituted 3-azidoazetidine-3-carboxylic acids as precursors. The conformational preferences of the newly synthesized peptides were investigated in solution by IR and NMR spectroscopy. It was observed that the 3-aminoazetidine-3-carboxylic acid moiety is likely a -turn inducer. In addition, an interesting main-chain-to-side-chain hydrogen bond that forms a six-membered pseudo-cycle was detected. It connects the nitrogen (acceptor) of the azetidine ring to the amide NH (donor) of the immediately following residue. This unexpected hydrogen bond increases the number of conformational options offered by N-substituted 3-aminoazetidine-3-carboxylic acids when designing foldamers with new and predictable 3D structures.
Keywords
Conformation analysis, Peptides, Amino acids, Nitrogen heterocycles, ALPHA-AMINO-ACIDS, TRICHOGIN GA IV, LEUKEMIA HL-60 CELLS, STEREOSELECTIVE-SYNTHESIS, CYCLIC TETRAPEPTIDE, RECEPTOR ANTAGONIST, EFRAPEPTIN-C, ALAMETHICIN, DERIVATIVES, PROTEIN

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Chicago
Žukauskaitė, Asta, Alessandro Moretto, Cristina Peggion, Marta De Zotti, Algirdas Sačkus, Fernando Formaggio, Norbert De Kimpe, and Sven Mangelinckx. 2014. “Synthesis and Conformational Study of Model Peptides Containing N-substituted 3-aminoazetidine-3-carboxylic Acids.” European Journal of Organic Chemistry 2014 (11): 2312–2321.
APA
Žukauskaitė, A., Moretto, A., Peggion, C., De Zotti, M., Sačkus, A., Formaggio, F., De Kimpe, N., et al. (2014). Synthesis and conformational study of model peptides containing N-substituted 3-aminoazetidine-3-carboxylic acids. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014(11), 2312–2321.
Vancouver
1.
Žukauskaitė A, Moretto A, Peggion C, De Zotti M, Sačkus A, Formaggio F, et al. Synthesis and conformational study of model peptides containing N-substituted 3-aminoazetidine-3-carboxylic acids. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 2014;2014(11):2312–21.
MLA
Žukauskaitė, Asta, Alessandro Moretto, Cristina Peggion, et al. “Synthesis and Conformational Study of Model Peptides Containing N-substituted 3-aminoazetidine-3-carboxylic Acids.” EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 2014.11 (2014): 2312–2321. Print.
@article{4413127,
  abstract     = {Model peptides containing N-substituted 3-aminoazetidine-3-carboxylic acids have been synthesized to investigate the conformational features of these C-tetrasubstituted amino acids. The target peptides were designed and prepared by classical synthetic methods in solution, exploiting the convenient N-substituted 3-azidoazetidine-3-carboxylic acids as precursors. The conformational preferences of the newly synthesized peptides were investigated in solution by IR and NMR spectroscopy. It was observed that the 3-aminoazetidine-3-carboxylic acid moiety is likely a -turn inducer. In addition, an interesting main-chain-to-side-chain hydrogen bond that forms a six-membered pseudo-cycle was detected. It connects the nitrogen (acceptor) of the azetidine ring to the amide NH (donor) of the immediately following residue. This unexpected hydrogen bond increases the number of conformational options offered by N-substituted 3-aminoazetidine-3-carboxylic acids when designing foldamers with new and predictable 3D structures.},
  author       = {Žukauskaitė, Asta and Moretto, Alessandro and Peggion, Cristina and De Zotti, Marta and Sačkus, Algirdas and Formaggio, Fernando and De Kimpe, Norbert and Mangelinckx, Sven},
  issn         = {1434-193X},
  journal      = {EUROPEAN JOURNAL OF ORGANIC CHEMISTRY},
  keywords     = {Conformation analysis,Peptides,Amino acids,Nitrogen heterocycles,ALPHA-AMINO-ACIDS,TRICHOGIN GA IV,LEUKEMIA HL-60 CELLS,STEREOSELECTIVE-SYNTHESIS,CYCLIC TETRAPEPTIDE,RECEPTOR ANTAGONIST,EFRAPEPTIN-C,ALAMETHICIN,DERIVATIVES,PROTEIN},
  language     = {eng},
  number       = {11},
  pages        = {2312--2321},
  title        = {Synthesis and conformational study of model peptides containing N-substituted 3-aminoazetidine-3-carboxylic acids},
  url          = {http://dx.doi.org/10.1002/ejoc.201301741},
  volume       = {2014},
  year         = {2014},
}

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