Conformational analysis of oligothiophenes and oligo(thienyl)furans by use of a combined molecular dynamics/NMR spectroscopic protocol

被引:10
作者
Diaz-Quijada, GA
Weinberg, N
Holdcroft, S [1 ]
Pinto, BM
机构
[1] Simon Fraser Univ, Dept Chem, Burnaby, BC V5A 1S6, Canada
[2] Univ Coll Fraser Valley, Dept Chem, Abbortsford, BC V2S 7M8, Canada
关键词
D O I
10.1021/jp011784l
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The conformational analysis of oligothiophenes and oligo(thienyl)furans by use of a combined molecular dynamics (MD)/NMR spectroscopic protocol is described. A series of MD simulations were performed for 2-(2'-thienyl)-3-hexylthiophene (2), 2,5-bis(3'-hexyl-2'-thienyl)thiophene (3), 2,5-bis(4'-hexyl-2'-thienyl)thiophene (4), 2,5-bis(3'-hexyl-2'-thienyl)furan (5), and 2,5-bis(4'-hexyl-2'-thienyl)furan (6) with a new MM2 torsional parameter set developed earlier for unsubstituted and methyl-substituted 2,2'-bithiophene and 2-(2'-thienyl)furan systems. Conformationally averaged structures were determined for each of these molecules. Theoretical NOE buildup curves were then calculated for these averaged structures using a full matrix relaxation treatment and were compared to those obtained experimentally. Excellent agreement between the calculated and experimental NOE buildup curves was generally observed, in particular for the 2,2'-bithiophene systems.
引用
收藏
页码:1277 / 1285
页数:9
相关论文
共 50 条
[21]   Conformational features of 4-(N)-squalenoyl-gemcitabine in solution: a combined NMR and molecular dynamics investigation [J].
Maurizio, Ceruti ;
Flavio, Rocco ;
Enrica, Di Pietro Maria ;
Elena, Tocci ;
Giuseppina, De Luca .
NEW JOURNAL OF CHEMISTRY, 2015, 39 (05) :3484-3496
[22]   A combined NMR and molecular dynamics simulation study to determine the conformational properties of agonists and antagonists against experimental autoimmune encephalomyelitis [J].
Mantzourani, Efthimia D. ;
Blokar, Klemen ;
Tselios, Theodore V. ;
Matsoukas, John M. ;
Platts, James A. ;
Mavromoustakos, Thomas M. ;
Grdadolnik, Simona Golic .
BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (05) :2171-2182
[23]   CONFORMATIONAL-ANALYSIS OF CARBOHYDRATES INFERRED FROM NMR-SPECTROSCOPY AND MOLECULAR MODELING - APPLICATIONS TO THE BEHAVIOR OF OLIGO-GALACTOMANNAN CHAINS [J].
TARAVEL, FR ;
MAZEAU, K ;
TVAROSKA, I .
BRAZILIAN JOURNAL OF MEDICAL AND BIOLOGICAL RESEARCH, 1995, 28 (07) :723-732
[24]   SYNTHESIS AND CONFORMATIONAL-ANALYSIS OF N-GLYCOPEPTIDES .2. CD, MOLECULAR-DYNAMICS, AND NMR SPECTROSCOPIC STUDIES ON LINEAR N-GLYCOPEPTIDES [J].
PERCZEL, A ;
KOLLAT, E ;
HOLLOSI, M ;
FASMAN, GD .
BIOPOLYMERS, 1993, 33 (04) :665-685
[25]   CONFORMATIONAL-ANALYSIS OF A CONDENSED MACROCYCLIC BETA-LACTAM BY NMR AND MOLECULAR-DYNAMICS CALCULATIONS [J].
KESERU, GM ;
VASARHELYI, H ;
MAKARA, G .
JOURNAL OF MOLECULAR STRUCTURE, 1994, 326 :151-155
[26]   Application of Paramagnetic NMR-Validated Molecular Dynamics Simulation to the Analysis of a Conformational Ensemble of a Branched Oligosaccharide [J].
Zhang, Ying ;
Yamamoto, Sayoko ;
Yamaguchi, Takumi ;
Kato, Koichi .
MOLECULES, 2012, 17 (06) :6658-6671
[27]   CONFORMATIONAL-ANALYSIS OF BRADYKININ BY ANNEALED MOLECULAR-DYNAMICS AND COMPARISON TO NMR-DERIVED CONFORMATIONS [J].
SALVINO, JM ;
SEOANE, PR ;
DOLLE, RE .
JOURNAL OF COMPUTATIONAL CHEMISTRY, 1993, 14 (04) :438-444
[28]   USE OF MOLECULAR-DYNAMICS METHODS IN CONFORMATIONAL-ANALYSIS - GLYCOL - A MODEL STUDY [J].
HOOFT, RWW ;
VANEIJCK, BP ;
KROON, J .
JOURNAL OF CHEMICAL PHYSICS, 1992, 97 (05) :3639-3646
[29]   CONFORMATIONAL-ANALYSIS OF N,N-DIISOPROPYLAMIDES BY COMBINED USE OF NMR LANTHANIDE-INDUCED SHIFTS AND CONFORMATIONAL ENERGY CALCULATIONS [J].
GRAHAM, LL ;
VANDERKOOI, G ;
GETZ, JA .
ORGANIC MAGNETIC RESONANCE, 1977, 9 (02) :80-89
[30]   Conformational analysis of hexapseudopeptides mimicking reverse turn structures induced by a modified (S)-proline. A combined spectroscopic and molecular dynamics investigation. Part 4 [J].
Balducci, Daniele ;
Bottoni, Andrea ;
Calvaresi, Matteo ;
Porzi, Gianni .
MOLECULAR PHYSICS, 2009, 107 (07) :653-663