Succinimidyl Carbamate Derivatives from <i>N</i>‐Protected α‐Amino Acids and Dipeptides―Synthesis of Ureidopeptides and Oligourea/Peptide Hybrids

Fischer, Lucile; Semetey, Vincent; Lozano, José Manuel; Schaffner, Arnaud‐Pierre; Briand, Jean‐Paul; Didierjean, Claude; Guichard, Gilles

doi:10.1002/ejoc.200700541

Cited by 11 publications

(17 citation statements)

References 1 publication

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“…Figure 1. This observation is in line with previous IR and 1 H-NMR spectroscopic investigations of model N-Boc-N'-carbamoyl-gem-diaminoalkyl derivatives in low polar solvents showing that the urea moiety adopts a stable cis,trans conformation that can be stabilized by an intramolecular H-bond (the "urea turn") [4]. Observed ROEs in 1 are compatible with the population of consecutive urea turns.…”

Section: Ch Of the Gval Residue (Figure 1) A Short Interproton Distasupporting

confidence: 88%

Mixing Urea and Amide Bonds: Synthesis and Self-Organization of New Hybrid Oligomers

Fischer

Lena

Briand

et al. 2009

Advances in Experimental Medicine and Biology

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Section: Ch Of the Gval Residue (Figure 1) A Short Interproton Distasupporting

confidence: 88%

Mixing Urea and Amide Bonds: Synthesis and Self-Organization of New Hybrid Oligomers

Fischer

Lena

Briand

et al. 2009

Advances in Experimental Medicine and Biology

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“…to the free amino group of the resin-bound peptide in DMF (2 mL) in presence of Hünig’s base (DIEA, 4 equivalents) twice for 120 min [ 45 ]. At the end of that time the Kaiser ninhydrin test [ 46 ] was negative. The Fmoc group was deprotected with 20% piperidine in DMF, and the last amino acids were introduced with standard solid-phase peptide synthesis procedures.…”

Section: The Peptide Bond As An Immunotherapeutic Target For Molecmentioning

confidence: 99%

Development of Designed Site-Directed Pseudopeptide-Peptido-Mimetic Immunogens as Novel Minimal Subunit-Vaccine Candidates for Malaria

et al. 2010

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Synthetic vaccines constitute the most promising tools for controlling and preventing infectious diseases. When synthetic immunogens are designed from the pathogen native sequences, these are normally poorly immunogenic and do not induce protection, as demonstrated in our research. After attempting many synthetic strategies for improving the immunogenicity properties of these sequences, the approach consisting of identifying high binding motifs present in those, and then performing specific changes on amino-acids belonging to such motifs, has proven to be a workable strategy. In addition, other strategies consisting of chemically introducing non-natural constraints to the backbone topology of the molecule and modifying the α-carbon asymmetry are becoming valuable tools to be considered in this pursuit. Non-natural structural constraints to the peptide backbone can be achieved by introducing peptide bond isosters such as reduced amides, partially retro or retro-inverso modifications or even including urea motifs. The second can be obtained by strategically replacing L-amino-acids with their enantiomeric forms for obtaining both structurally site-directed designed immunogens as potential vaccine candidates and their Ig structural molecular images, both having immuno-therapeutic effects for preventing and controlling malaria.

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“…Ureidopeptidomimetics have their peptide bonds (−C(O)NH−) substituted by urea (−HNC(O)NH−) and have been synthesized with various substituents on either ends of the peptide chain . These molecules have potential applications in the field of drug delivery, sensors, and molecular devices .…”

Section: Introductionmentioning

confidence: 99%

Density functional theoretical studies on photoswitching and charge migration dynamics of thio and selenoureidopeptides

2017

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Density functional theoretical calculations have been performed to investigate the changes in electronic structure at ground and excited states of ureidopeptides on substitution with higher chalcogens like sulphur and selenium for oxygen. This replacement results in a reduced preference towards the intramolecular hydrogen bonding interaction, thus linear conformers are found to be stable at both states.Nevertheless, conformational switching observed during this process is mainly due to n to π* transition that leads to the dihedral angle ω change from trans to cis with a rotational barrier of 10 to 17 kcal mol -1 . The computed barrier is lesser than that reported for oxopeptides (20 kcal mol -1 ). And, the hole migration dynamics after immediate ionization illustrates that the hole originated at ureido end evolves in time (2−4 fs) while the hole generated at the carboxylate end will not evolve as reported for ureidopeptides. The usage of these candidates as photoswitches has also been explored.

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Succinimidyl Carbamate Derivatives from N‐Protected α‐Amino Acids and Dipeptides―Synthesis of Ureidopeptides and Oligourea/Peptide Hybrids

Cited by 11 publications

References 1 publication

Mixing Urea and Amide Bonds: Synthesis and Self-Organization of New Hybrid Oligomers

Mixing Urea and Amide Bonds: Synthesis and Self-Organization of New Hybrid Oligomers

Development of Designed Site-Directed Pseudopeptide-Peptido-Mimetic Immunogens as Novel Minimal Subunit-Vaccine Candidates for Malaria

Density functional theoretical studies on photoswitching and charge migration dynamics of thio and selenoureidopeptides

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