Crystal structure of 4-[(1 R,2 S,5 R)-2-isopropyl-5-methyl-cyclo-hex-yl] 2-methyl (2 S,4 S,5 R)-1-[(2 S,3 R,5 R)-5-meth-oxy-carbonyl-2-(2-methyl-phen-yl)pyrrolidine-3-carbon-yl]-5-(2-methyl-phen-yl)pyrrolidine-2,4-di-carboxyl-ate

Polina M Ivantcova; Mikhail N Sokolov; Konstantin V Kudryavtsev; Andrei V Churakov

doi:10.1107/S2056989019004079

Crystal structure of 4-[(1 R,2 S,5 R)-2-isopropyl-5-methyl-cyclo-hex-yl] 2-methyl (2 S,4 S,5 R)-1-[(2 S,3 R,5 R)-5-meth-oxy-carbonyl-2-(2-methyl-phen-yl)pyrrolidine-3-carbon-yl]-5-(2-methyl-phen-yl)pyrrolidine-2,4-di-carboxyl-ate

Acta Crystallogr E Crystallogr Commun. 2019 Apr 2;75(Pt 5):537-539. doi: 10.1107/S2056989019004079. eCollection 2019 May 1.

Authors

Polina M Ivantcova¹, Mikhail N Sokolov¹, Konstantin V Kudryavtsev¹, Andrei V Churakov²

Affiliations

¹ Department of Chemistry, M.V. Lomonosov Moscow State University, Leninskie Gory 1/3, Moscow 119991, Russian Federation.
² Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninskii prosp. 31, Moscow 119991, Russian Federation.

Abstract

The title compound, C₃₈H₅₀N₂O₇, represents a chiral β-proline dipeptide. Corresponding stereogenic centres of constituting pyrrolidine units have opposite absolute configurations. The central amide fragment is planar within 0.1 Å and adopts a Z configuration along the N-CO bond. In the crystal, the hydrogen atoms of the methyl-ene groups form several short inter-molecular C-H⋯O contacts with the carbonyl oxygen atoms of an adjacent mol-ecule. The only active amino hydrogen atom is not involved in hydrogen bonding.

Keywords: crystal structure; peptide bond configuration; β-peptides; β-proline oligomers.

Grants and funding

This work was funded by Russian Foundation for Basic Research grant 18-33-01260 to M. N. Sokolov. Scholarship of the President of the Russian Federation grant SP-1278.2018.4 to P. M. Ivantcova.