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Structure and conformation of the sodium chloride salt of N-t-Boc-Phenylalanyl-Proline (Boc-Phe-Pro·NaCl) and the dihydrate of N-t-Boc-Tyrosyl-Proline (Boc-Tyr-Pro·2H2O)

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Abstract

The structure and conformation of the salt of N-t-Boc-Phenylalanyl-Proline (Boc-Phe-Pro·NaCl) (C19H26N2O5NaCl) (compound 2) and the dihydrate of N-t-Boc-Tyrosyl-Proline (Boc-Tyr-Pro·2H2O) (C19H30O8N2) (compound 1) have been investigated with X-ray crystallographic and spectroscopic methods. Boc-Phe-Pro·NaCl crystallizeds in an extended trans conformation in the space groupP21 with cell dimensionsa=7.961 (3),b=10.045(2), andc=13.495(4). One intermolecular hydrogen bond and one intramolecular hydrogen bond was observed for the dipeptide salt. Boc-Tyr-Pro·2H2O crystallized in an extended trans conformation in the space group P21 with cell dimensionsa=7.964(1),b=10.011(1), andc=13.853(2). Six intermolecular hydrogen bonds were observed for Boc-Tyr-Pro·2H2O. The conformation of both dipeptides reflect collagen-type of proline-compounds. The puckering mode of the pyrrolidine ring of the proline residues can be described as an approximate C2 half-chair symmetry having an A conformation with the Cγ atom located exo and Cβ atom located endo relative to the carboxamide group, i.e., γ/β T.Cis-trans isomerism was observed in the NMR spectra of both dipeptides with a predominance for the extended side chain for the phenylalanyl and tyrosyl residues, respectively.

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Authors and Affiliations

  1. School of Pharmacy, University of Port Elizabeth, Box 1600, 6000, Port Elizabeth, Republic of South Africa

    P. J. Milne

  2. Department of Pharmacology, Potchefstroom University of C.H.E., 2520, Potchefstroom, Republic of South Africa

    D. W. Oliver

  3. Department of Chemistry, University of Pretoria, 0001, Pretoria, Republic of South Africa

    P. H. Van Rooyen & H. M. Roos

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  1. P. J. Milne
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  2. D. W. Oliver
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  3. P. H. Van Rooyen
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  4. H. M. Roos
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Milne, P.J., Oliver, D.W., Van Rooyen, P.H. et al. Structure and conformation of the sodium chloride salt of N-t-Boc-Phenylalanyl-Proline (Boc-Phe-Pro·NaCl) and the dihydrate of N-t-Boc-Tyrosyl-Proline (Boc-Tyr-Pro·2H2O). J Chem Crystallogr 27, 167–175 (1997). https://doi.org/10.1007/BF02575985

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