Captopril and its dimer captopril disulfide: comparative structural and conformational studies

Acta Crystallographica. Section C, Structural Chemistry
Joanna BojarskaMilan Remko

Abstract

The crystal structures of captopril {systematic name: (2S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]pyrrolidine-2-carboxylic acid}, C(9)H(15)NO(3)S, (1), and its dimer disulfide metabolite, 1,1'-{disulfanediylbis[(2S)-2-methyl-1-oxopropane-3,1-diyl]}bis-L-proline, C(18)H(28)N(2)O(6)S(2), (2), were determined by single-crystal X-ray diffraction analysis. Compound (1) crystallizes in the orthorhombic space group P2(1)2(1)2(1), while compound (2) crystallizes in the monoclinic space group P2(1), both with one molecule per asymmetric unit. The molecular geometries of (1) and (2) are quite similar, but certain differences appear in the conformations of the five-membered proline rings and the side chains containing the sulfhydryl group. The proline ring adopts an envelope conformation in (1), while in (2) it exists in envelope and slightly deformed half-chair conformations. The conformation adopted by the side chain is extended in (1) and folded in (2). A minimum-energy conformational search using Monte Carlo methods in the aqueous phase reveals that the optimized conformations of the title compounds differ from those determined crystallographically, which depend on their immediate environment. Intermolecular O-H...O and relatively weak ...Continue Reading

References

Apr 1, 1990·Acta Crystallographica. Section B, Structural Science·M C EtterJ Bernstein
Dec 25, 2007·Acta Crystallographica. Section A, Foundations of Crystallography·George M Sheldrick
Oct 8, 2008·Annals of the New York Academy of Sciences·Samir AttoubGeorg Petroianu
Jan 28, 2009·Acta Crystallographica. Section D, Biological Crystallography·Anthony L Spek
Sep 1, 2012·Acta Crystallographica. Section C, Crystal Structure Communications·Joanna BojarskaMilan Remko
Nov 6, 2012·Acta Crystallographica. Section C, Crystal Structure Communications·Joanna BojarskaMilan Remko
May 31, 2013·Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials·Simon ParsonsTrixie Wagner
Jun 8, 2013·Acta Crystallographica. Section C, Crystal Structure Communications·Joanna BojarskaMilan Remko
Jan 3, 2014·Angewandte Chemie·Colin R Groom, Frank H Allen
Jan 9, 2015·Acta Crystallographica. Section C, Structural Chemistry·George M Sheldrick

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Citations

Jan 21, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Vasso ApostolopoulosIstvan Toth
Jul 23, 2021·Langmuir : the ACS Journal of Surfaces and Colloids·Valeria CastellettoIan W Hamley

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