Pregled bibliografske jedinice broj: 254718
Attempted diastereoselective preparation and chiroptical properties of (2S)-1-(3-mercapto-2-methyl-1-oxopropyl)-L-proline (captopril) and some congeners
Attempted diastereoselective preparation and chiroptical properties of (2S)-1-(3-mercapto-2-methyl-1-oxopropyl)-L-proline (captopril) and some congeners // Croatica Chemica Acta, 62 (1989), 2B; 325-338 (međunarodna recenzija, članak, znanstveni)
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Naslov
Attempted diastereoselective preparation and chiroptical properties of (2S)-1-(3-mercapto-2-methyl-1-oxopropyl)-L-proline (captopril) and some congeners
Autori
Snatzke, G. ; Decorte, E. ; Kovač, T. ; Moimas, F. ; Habuš, Ivan ; Šunjić, Vitomir
Izvornik
Croatica Chemica Acta (0011-1643) 62
(1989), 2B;
325-338
Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni
Ključne riječi
(2S)-1-(3-mercapto-2-methyl-1-oxopropyl)-L-proline (captopril, 1)
Sažetak
CD and 13C-NMR study of the conformational properties of (2S)-1-(3-mercapto-2-methyl-1-oxopropyl)-L-proline (captopril, 1), and its congeners 2-5, 8, 9 is reported. 13C-NMR data (in DMSO-d6) reveal an E/Z (cis/trans) ratio of ca. (15-30) : (70-85) for the N-acyl-prolines 1, 5, 10, and for N-acetyl-L-proline. CD data indicate practically identical conformations for the ring systems of 8 and 9. Attempted diastereoselective cyclization of the sodium salt of 7 or the free thioacid into 8 and 9 resulted in low chemical yields (~30%) and low diastereoselectivity, favouring formation of the "wrong" diastereomer 9 in small excess (~20%).
Izvorni jezik
Engleski
Znanstvena područja
Kemija
POVEZANOST RADA
Ustanove:
Institut "Ruđer Bošković", Zagreb
Citiraj ovu publikaciju:
Časopis indeksira:
- Current Contents Connect (CCC)
- Web of Science Core Collection (WoSCC)
- Science Citation Index Expanded (SCI-EXP)
- SCI-EXP, SSCI i/ili A&HCI
