Reverse turn conformation of N-thioacetyl thioprolyl glycine N′-methylamide in the crystal and in solution

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

The molecular structure of Act-Prot-Gly-NHCH3/AcΨ (CSNH)-ProΨ (CSNH)-Gly-NHCH3/ (1) is reported. In the crystal 1 adopts a conformation with a Z(trans) tertiary (thioacetyl pyrrolidine) thioamide bond and torsion angles (Φ2 = -73.2°, Ψ2 = 151.9°, Φ3 = 83.5°, Ψ3 = 5.5°) which are rather close to the values of a type II β-turn. The sulfur atom of the thioacetyl group is the acceptor of a 1←4 intramolecular H-bond. Based on 400 MHz 1H and 13C NMR studies, including 1H NOE experiments, the conformational equilibrium in CDCl3 solution is dominated by the conformer which is present in the crystal. The chiroptical properties of 1 are also discussed, in comparison to those of mono- and dithionated models of β-turns.

Original languageEnglish
Pages (from-to)6661-6668
Number of pages8
JournalTetrahedron
Volume49
Issue number30
DOIs
Publication statusPublished - Jul 23 1993

Fingerprint

Thioamides
Molecular Structure
Sulfur
Glycine
Conformations
Crystals
Torsional stress
Molecular structure
Nuclear magnetic resonance
Atoms
Experiments
Proton Magnetic Resonance Spectroscopy
pyrrolidine
Carbon-13 Magnetic Resonance Spectroscopy

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

@article{eb5d4f21a419421d996212531cc58e36,
title = "Reverse turn conformation of N-thioacetyl thioprolyl glycine N′-methylamide in the crystal and in solution",
abstract = "The molecular structure of Act-Prot-Gly-NHCH3/AcΨ (CSNH)-ProΨ (CSNH)-Gly-NHCH3/ (1) is reported. In the crystal 1 adopts a conformation with a Z(trans) tertiary (thioacetyl pyrrolidine) thioamide bond and torsion angles (Φ2 = -73.2°, Ψ2 = 151.9°, Φ3 = 83.5°, Ψ3 = 5.5°) which are rather close to the values of a type II β-turn. The sulfur atom of the thioacetyl group is the acceptor of a 1←4 intramolecular H-bond. Based on 400 MHz 1H and 13C NMR studies, including 1H NOE experiments, the conformational equilibrium in CDCl3 solution is dominated by the conformer which is present in the crystal. The chiroptical properties of 1 are also discussed, in comparison to those of mono- and dithionated models of β-turns.",
author = "M. Czugler and A. K{\'a}lm{\'a}n and M. Kajt{\'a}r-Peredy and Emma Koll{\'a}t and Judit Kajt{\'a}r and Zs. Majer and O. Farkas and M. Holl{\'o}si",
year = "1993",
month = "7",
day = "23",
doi = "10.1016/S0040-4020(01)81836-6",
language = "English",
volume = "49",
pages = "6661--6668",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "30",

}

TY - JOUR

T1 - Reverse turn conformation of N-thioacetyl thioprolyl glycine N′-methylamide in the crystal and in solution

AU - Czugler, M.

AU - Kálmán, A.

AU - Kajtár-Peredy, M.

AU - Kollát, Emma

AU - Kajtár, Judit

AU - Majer, Zs.

AU - Farkas, O.

AU - Hollósi, M.

PY - 1993/7/23

Y1 - 1993/7/23

N2 - The molecular structure of Act-Prot-Gly-NHCH3/AcΨ (CSNH)-ProΨ (CSNH)-Gly-NHCH3/ (1) is reported. In the crystal 1 adopts a conformation with a Z(trans) tertiary (thioacetyl pyrrolidine) thioamide bond and torsion angles (Φ2 = -73.2°, Ψ2 = 151.9°, Φ3 = 83.5°, Ψ3 = 5.5°) which are rather close to the values of a type II β-turn. The sulfur atom of the thioacetyl group is the acceptor of a 1←4 intramolecular H-bond. Based on 400 MHz 1H and 13C NMR studies, including 1H NOE experiments, the conformational equilibrium in CDCl3 solution is dominated by the conformer which is present in the crystal. The chiroptical properties of 1 are also discussed, in comparison to those of mono- and dithionated models of β-turns.

AB - The molecular structure of Act-Prot-Gly-NHCH3/AcΨ (CSNH)-ProΨ (CSNH)-Gly-NHCH3/ (1) is reported. In the crystal 1 adopts a conformation with a Z(trans) tertiary (thioacetyl pyrrolidine) thioamide bond and torsion angles (Φ2 = -73.2°, Ψ2 = 151.9°, Φ3 = 83.5°, Ψ3 = 5.5°) which are rather close to the values of a type II β-turn. The sulfur atom of the thioacetyl group is the acceptor of a 1←4 intramolecular H-bond. Based on 400 MHz 1H and 13C NMR studies, including 1H NOE experiments, the conformational equilibrium in CDCl3 solution is dominated by the conformer which is present in the crystal. The chiroptical properties of 1 are also discussed, in comparison to those of mono- and dithionated models of β-turns.

UR - http://www.scopus.com/inward/record.url?scp=0027171947&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0027171947&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(01)81836-6

DO - 10.1016/S0040-4020(01)81836-6

M3 - Article

AN - SCOPUS:0027171947

VL - 49

SP - 6661

EP - 6668

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 30

ER -