Aminosäuren, 17 – Eine neue Synthese von Didehydrodipeptiden und Didehydrotripeptiden

Autor:	Uwe Stelzer, Franz Effenberger, Jürgen Kühlwein, Martin Hopf
Rok vydání:	1993
Předmět:	chemistry.chemical_classification Dipeptide Stereochemistry Organic Chemistry Tripeptide Amino acid Acylation chemistry.chemical_compound Hydrolysis chemistry Peptide synthesis Azide Physical and Theoretical Chemistry Racemization
Zdroj:	Liebigs Annalen der Chemie. 1993:1303-1311
ISSN:	1099-0690 0170-2041
DOI:	10.1002/jlac.1993199301212
Popis:	Amino Acids, 17. – A New Synthesis of Didehydro Dipeptides and Didehydro Tripeptides Esters of N-phthaloyl-protected (R)- or (S)-didehydro dipeptides 5–7 were obtained in good yields by the perrhenate-catalyzed decomposition of 2-azidocarboxylates 1 with N-phthaloyl-protected (R)- or (S)-amino acid chlorides 2 in presence of at least equimolar amounts of N-methyl-2-pyridone (4) as acylation catalyst. Esters of didehydro tripeptides 16 were obtained in a comparable procedure from the optically active amino acid chlorides 2 and 2-(2-azidoacyl)amino acid esters 15, which were prepared from 2-azidocarboxylic acids 12 or the corresponding chlorides 13 with 2-amino acid ester hydrochlorides (S)-14. – As an example, the unprotected (S)-alanly-didehydrovalin 20 was prepared from the didehydro dipeptide 18a without any racemization by hydrolysis of the benzyl ester and subsequent hydrogenolytic removal of the N-phthaloyl group.
Databáze:	OpenAIRE
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