Laulimalide is one of the newest naturally occurring macrolides known to act as a microtubule stabilizing agent with properties similar to Taxol. It also stands as being one of the most flexible with 18 rotatable bonds. This large number of rotatable bonds allows for approximately 3(18) potential conformers. To examine the conformational energy surface of laulimalide, we have performed an NAMFIS deconvolution analysis for laulimalide in DMSO-d(6)-. The latter has been supplemented with a post-NAMFIS energy analysis at the Becke3LYP/6-31 G* level that examines the opposing effects of internal hydrogen bonding and synpentane interactions. In this way, we have identified 15 laulimalide conformations that can be classified into 5 different families: Supine, Convex, Cobra, Stretch, and Concave motifs.

Thepchatri, P., Cicero, D.O., Monteagudo, E., Ghosh, A.K., Cornett, B., Weeks, E.R., et al. (2005). Conformations of laulimalide in DMSO-d6. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 127(37), 12838-12846 [10.1021/ja042890e].

Conformations of laulimalide in DMSO-d6

CICERO, DANIEL OSCAR;
2005

Abstract

Laulimalide is one of the newest naturally occurring macrolides known to act as a microtubule stabilizing agent with properties similar to Taxol. It also stands as being one of the most flexible with 18 rotatable bonds. This large number of rotatable bonds allows for approximately 3(18) potential conformers. To examine the conformational energy surface of laulimalide, we have performed an NAMFIS deconvolution analysis for laulimalide in DMSO-d(6)-. The latter has been supplemented with a post-NAMFIS energy analysis at the Becke3LYP/6-31 G* level that examines the opposing effects of internal hydrogen bonding and synpentane interactions. In this way, we have identified 15 laulimalide conformations that can be classified into 5 different families: Supine, Convex, Cobra, Stretch, and Concave motifs.
Pubblicato
Rilevanza internazionale
Articolo
Sì, ma tipo non specificato
Settore BIO/10
English
Hydrogen bonds; Laulimalides; NAMFIS deconvolution; Synpentane interactions; Taxols; Organic compounds; cytotoxin; dimethyl sulfoxide; discodermolide; eleutherobin; epothilone A; laulimalide; macrolide; paclitaxel; peluroside A; pentane; sarcodictyin A; unclassified drug; article; chemical interaction; drug conformation; drug structure; energy transfer; hydrogen bond; structure analysis; Crystallography, X-Ray; Dimethyl Sulfoxide; Models, Molecular; Molecular Conformation; Taxoids
Thepchatri, P., Cicero, D.O., Monteagudo, E., Ghosh, A.K., Cornett, B., Weeks, E.R., et al. (2005). Conformations of laulimalide in DMSO-d6. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 127(37), 12838-12846 [10.1021/ja042890e].
Thepchatri, P; Cicero, Do; Monteagudo, E; Ghosh, A; Cornett, B; Weeks, E; Snyder, J
Articolo su rivista
File in questo prodotto:
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2108/34906
Citazioni
  • ???jsp.display-item.citation.pmc??? 13
  • Scopus 38
  • ???jsp.display-item.citation.isi??? 35
social impact