Solid-state structure of cyclic dipeptides: an X-ray and computational study of cis- and trans-diketo-piperazines of N-methyl-phenylalanine with the thia-pipecolic acids and thia-prolines

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F17%3A00483865" target="_blank" >RIV/61388963:_____/17:00483865 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/00216208:11310/17:10366459

Výsledek na webu

<a href="http://dx.doi.org/10.1107/S2052520617014731" target="_blank" >http://dx.doi.org/10.1107/S2052520617014731</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1107/S2052520617014731" target="_blank" >10.1107/S2052520617014731</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Solid-state structure of cyclic dipeptides: an X-ray and computational study of cis- and trans-diketo-piperazines of N-methyl-phenylalanine with the thia-pipecolic acids and thia-prolines

Popis výsledku v původním jazyce

Ten new crystal structures of cis and trans bicyclic diketopiperazines (DKPs) of thia-pipecolic acid (with sulfur in the beta, gamma or delta position) or thia-proline (with sulfur in the beta or gamma position) and N-methyl phenylalanine [(NMe) Phe]: cyclo[(beta-S) Pip-(NMe) Phe], cyclo[(gamma-S) Pip-(NMe) Phe], cyclo[(delta-S) Pip-(NMe) Phe], cyclo[(beta-S) Pro-(NMe) Phe] and cyclo[(beta-S) Pro-(NMe) Phe] were determined with X-ray crystallography. Density functional theory calculations of these molecules in the gas phase succeed in reproducing the observed molecular conformations in the crystal remarkably well. This illustrates the weak to moderate impact of intermolecular packing forces in the absence of classical N-H center dot center dot center dot center dot O hydrogen bonds. The effect of sulfur on the geometry of the DKP ring and details of amide bond non-planarity are discussed. Molecular flexibility of the DKP ring, as estimated from the calculated deformation energies of its endocyclic ring torsion angles, is not in general the decisive factor for the occurrence of multiple symmetry independent molecules in the unit cell (Z' > 1), though in some cases a correlation is observed.

Název v anglickém jazyce

Solid-state structure of cyclic dipeptides: an X-ray and computational study of cis- and trans-diketo-piperazines of N-methyl-phenylalanine with the thia-pipecolic acids and thia-prolines

Popis výsledku anglicky

Ten new crystal structures of cis and trans bicyclic diketopiperazines (DKPs) of thia-pipecolic acid (with sulfur in the beta, gamma or delta position) or thia-proline (with sulfur in the beta or gamma position) and N-methyl phenylalanine [(NMe) Phe]: cyclo[(beta-S) Pip-(NMe) Phe], cyclo[(gamma-S) Pip-(NMe) Phe], cyclo[(delta-S) Pip-(NMe) Phe], cyclo[(beta-S) Pro-(NMe) Phe] and cyclo[(beta-S) Pro-(NMe) Phe] were determined with X-ray crystallography. Density functional theory calculations of these molecules in the gas phase succeed in reproducing the observed molecular conformations in the crystal remarkably well. This illustrates the weak to moderate impact of intermolecular packing forces in the absence of classical N-H center dot center dot center dot center dot O hydrogen bonds. The effect of sulfur on the geometry of the DKP ring and details of amide bond non-planarity are discussed. Molecular flexibility of the DKP ring, as estimated from the calculated deformation energies of its endocyclic ring torsion angles, is not in general the decisive factor for the occurrence of multiple symmetry independent molecules in the unit cell (Z' > 1), though in some cases a correlation is observed.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10403 - Physical chemistry

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2017

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Acta Crystallographica. Section B: Structural Science, Crystal Engineering and Materials

ISSN

2052-5206

e-ISSN

—

Svazek periodika

73

Číslo periodika v rámci svazku

6

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

15

Strana od-do

1179-1193

Kód UT WoS článku

000417608600018

EID výsledku v databázi Scopus

2-s2.0-85037689474