Environment-dependent conformation of Boc-Pro-Ser-NHCH3

A. Perczel, M. Hollósi, V. Fulop, A. Kálmán, P. Sandor, G. D. Fasman

Research output: Contribution to journalArticle

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Abstract

The conformation of Boc-Pro-Ser-NHCH3 (1) was studied in the solid state and in solution. In the crystal, the steric structure of 1 is characterized by an E(cis) urethane tertiary amide bond and the lack of intramolecular H bonds. Four-hundred megahertz 1H- and 101-MHz 13C-nmr studies in CDCl3 clearly show the presence of two conformers differing in the rotameric state of the tertiary-amide bond. Selective 1H-13C nuclear Overhauser enhancement experiments at -20°C as well as 1H-nmr and ir data indicate that the major trans conformer (84% in CDCl3) may adopt a type I β-turn conformation with a possible O(γ) ··· H-N interaction, similarly to Piv-Pro-Ser-NHCH3 (2) [A. Aubry, N. Ghermani, and M. Marraud (1984) Int. J. Peptide Protein Res. 23, 113-122]. Molecular mechanics calculations on the cis rotamer show that the β-pleated-like backbone conformation of serine in the crystal of 1 is not a low-energy state for the isolated molecule; it is caused by packing forces, particularly by the helical network of intermolecular H bonds.

Original languageEnglish
Pages (from-to)763-771
Number of pages9
JournalBiopolymers - Peptide Science Section
Volume30
Issue number7-8
DOIs
Publication statusPublished - 1990

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prolyl-serine
Amides
Conformations
Urethane
Mechanics
Serine
Crystals
Molecular mechanics
Electron energy levels
Peptides
Proteins
Molecules
Experiments

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)
  • Biochemistry
  • Biophysics

Cite this

Environment-dependent conformation of Boc-Pro-Ser-NHCH3. / Perczel, A.; Hollósi, M.; Fulop, V.; Kálmán, A.; Sandor, P.; Fasman, G. D.

In: Biopolymers - Peptide Science Section, Vol. 30, No. 7-8, 1990, p. 763-771.

Research output: Contribution to journalArticle

Perczel, A. ; Hollósi, M. ; Fulop, V. ; Kálmán, A. ; Sandor, P. ; Fasman, G. D. / Environment-dependent conformation of Boc-Pro-Ser-NHCH3. In: Biopolymers - Peptide Science Section. 1990 ; Vol. 30, No. 7-8. pp. 763-771.
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AU - Fasman, G. D.

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