Studies on the synthesis of β-keto esters derived from dipeptides: search for a low-epimerizing method

Autor:	Rosario González-Muñiz, Mercedes Martín-Martínez, María Teresa García-López, Rosario Patiño-Molina, Rosario Herranz
Rok vydání:	2000
Předmět:	chemistry.chemical_classification Potassium Pharmacology toxicology Diastereomer chemistry.chemical_element Salt (chemistry) Bioengineering Biochemistry Analytical Chemistry Residue (chemistry) chemistry Yield (chemistry) Drug Discovery Molecular Medicine Organic chemistry Epimer
Zdroj:	Letters in Peptide Science. 7:143-149
ISSN:	1573-3904 0929-5666
DOI:	10.1007/bf02443581
Popis:	β-Keto esters derived from dipeptides are prepared by application of common methodologies employed for the synthesis of amino acid-derived β-keto esters; however, epimerization of the C-terminal residue occurred to different extents depending on the method. In imidazolide activated dipeptides, this epimerization is due to the CDI activation step and to the configurational instability of the intermediate imidazolides in different reaction media. Regarding yield and diastereomeric purity, the method of choice proved to be the reaction of dipeptide-derived imidazolide with the potassium salt of malonic half esters in the presence of MgCl2.
Databáze:	OpenAIRE
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