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Original scientific paper

Attempted Diastereoselective Preparation and Chiroptical Properties of (2S)-1-(3-Mercapto-2-Methyl-1-Oxopropyl)-L-Proline (Captopril) and Some Congeners

G. Snatzke ; Chair for Structural Chemistry, Ruhr University, D-4630 Bochum, FR Germany
E. Decorte ; CRC - Compagnia di Ricerca Chimica SpA, 1-33048 San Giovanni al Natisone (UD), Italy
T. Kovač ; CRC - Compagnia di Ricerca Chimica SpA, 1-33048 San Giovanni al Natisone (UD), Italy
F. Moimas ; CRC - Compagnia di Ricerca Chimica SpA, 1-33048 San Giovanni al Natisone (UD), Italy
L. Habuš ; "Ruđer Bošković" Institute, P.O. Box 1016, YU-41001 Zagreb, Croatia, Yugoslavia
V. Šunjić ; "Ruđer Bošković" Institute, P.O. Box 1016, YU-41001 Zagreb, Croatia, Yugoslavia

Fulltext: english, pdf (5 MB) pages 325-338 downloads: 76* cite
APA 6th Edition
Snatzke, G., Decorte, E., Kovač, T., Moimas, F., Habuš, L. & Šunjić, V. (1989). 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 (2B), 325-338. Retrieved from https://hrcak.srce.hr/175499
MLA 8th Edition
Snatzke, G., et al. "Attempted Diastereoselective Preparation and Chiroptical Properties of (2S)-1-(3-Mercapto-2-Methyl-1-Oxopropyl)-L-Proline (Captopril) and Some Congeners." Croatica Chemica Acta, vol. 62, no. 2B, 1989, pp. 325-338. https://hrcak.srce.hr/175499. Accessed 27 May 2020.
Chicago 17th Edition
Snatzke, G., E. Decorte, T. Kovač, F. Moimas, L. Habuš and V. Šunjić. "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, no. 2B (1989): 325-338. https://hrcak.srce.hr/175499
Harvard
Snatzke, G., et al. (1989). '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(2B), pp. 325-338. Available at: https://hrcak.srce.hr/175499 (Accessed 27 May 2020)
Vancouver
Snatzke G, Decorte E, Kovač T, Moimas F, Habuš L, Šunjić V. Attempted Diastereoselective Preparation and Chiroptical Properties of (2S)-1-(3-Mercapto-2-Methyl-1-Oxopropyl)-L-Proline (Captopril) and Some Congeners. Croatica Chemica Acta [Internet]. 1989 [cited 2020 May 27];62(2B):325-338. Available from: https://hrcak.srce.hr/175499
IEEE
G. Snatzke, E. Decorte, T. Kovač, F. Moimas, L. Habuš and V. Šunjić, "Attempted Diastereoselective Preparation and Chiroptical Properties of (2S)-1-(3-Mercapto-2-Methyl-1-Oxopropyl)-L-Proline (Captopril) and Some Congeners", Croatica Chemica Acta, vol.62, no. 2B, pp. 325-338, 1989. [Online]. Available: https://hrcak.srce.hr/175499. [Accessed: 27 May 2020]

Abstracts
CD and 13C-NMRstudy of the eonformational properties of (2S)-1-(3-mercapto-2-methyl-1-oxopropyl)-L-proline (captopril, 1), and its congeners 2-5, 8, 9 is reported. 13C-NMRdata (in DMSO-d6) reveal an E/Z (cis/trans) ratio of ea. (15-30) : (70-85) for the N-acetyl-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%).

Hrčak ID: 175499

URI
https://hrcak.srce.hr/175499

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