The epimerization of peptide aldehydes--a systematic study

Cécile Ganneau1, Aline Moulin, Luc Demange

  • 1Laboratoire des Aminoacides, Peptides et Protéines, LAPP, UMR 5810 CNRS Universités Montpellier I et II, Faculté de Pharmacie, 15 Avenue Charles Flahault,BP 14491, 34093 Montpellier Cédex 5, France.

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IUPAC Nomenclature of Aldehydes

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Common Names of Aldehydes and Ketones

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Common names of aldehydes are derived from the names of their corresponding acid. For instance, the two-carbon aldehyde–acetaldehyde derives its name from the corresponding acid–acetic acid. Similarly, formaldehyde derives its name from formic acid and benzaldehyde from benzoic acid.
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Alkylation of β-Diester Enolates: Malonic Ester Synthesis

Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis01:07

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an alkylated β-keto acid.
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In aldehydes, the hydrogen atom connected to the carbonyl carbon helps distinguish aldehydes from other carbonyl compounds using ¹H NMR spectroscopy. The closeness of aldehydic hydrogen to the electrophilic carbonyl carbon highly deshields the hydrogen atom causing its signal to appear around 10 ppm in the ¹H NMR spectra. α hydrogens split the aldehydic proton signal, which helps identify the number of α hydrogens in the molecule. For instance, one α hydrogen creates a doublet for an aldehydic...
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Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones

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