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http://dx.doi.org/10.18419/opus-1171
Autor(en): | Effenberger, Franz Kühlwein, Jürgen Hopf, Martin Stelzer, Uwe |
Titel: | Eine neue Synthese von Didehydrodipeptiden und Didehydrotripeptiden (Aminosäuren ; 17) |
Sonstige Titel: | A new synthesis of didehydro dipeptides and didehydro tripeptides (Amino acids ; 17) |
Erscheinungsdatum: | 1993 |
Dokumentart: | Zeitschriftenartikel |
Erschienen in: | Justus Liebigs Annalen der Chemie (1993), S. 1303-1311. URL http://dx.doi.org./10.1002/jlac.1993199301212 |
URI: | http://nbn-resolving.de/urn:nbn:de:bsz:93-opus-44558 http://elib.uni-stuttgart.de/handle/11682/1188 http://dx.doi.org/10.18419/opus-1171 |
Zusammenfassung: | 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. |
Enthalten in den Sammlungen: | 03 Fakultät Chemie |
Dateien zu dieser Ressource:
Datei | Beschreibung | Größe | Format | |
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eff246.pdf | 968,32 kB | Adobe PDF | Öffnen/Anzeigen |
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