Title
Design and synthesis of bombykol analogues for probing pheromone-binding protein-ligand interactions
Date Issued
31 January 2009
Access level
metadata only access
Resource Type
journal article
Author(s)
Instituto Max Planck de Ecología Química
Abstract
Mono-, difluorinated, and thioanalogues of Bombyx mori female sex pheromones (bombykol, 1) were designed according to the ab initio calculations. These rationally designated analogues were synthesized using hydroboration and Sonogashira coupling strategy via (5E,7Z)-undecadien-1-ol (10) as a common intermediate. A new simplified binding assay based on nanoLC-linear ion trap ESI-MS for quantifying complexation of the B. mori pheromone-binding protein (BmPBP) with native (1) and prepared analogues was developed. The binding properties of native 1 and thioanalogue 4 with PBP were studied in detail. The dissociation constant (KD) of 1 and 4 was determined to be 2.1×10-6 M and 2.4×10-6 M, respectively. The similar values for both ligands correlated with ab initio calculations. The new binding assay could be used to determine the KD of other PBPs. © 2008 Elsevier Ltd. All rights reserved.
Start page
1069
End page
1076
Volume
65
Issue
5
Language
English
OCDE Knowledge area
Ingeniería química
Química orgánica
Scopus EID
2-s2.0-57649188044
Source
Tetrahedron
ISSN of the container
00404020
Source funding
Max-Planck-Gesellschaft
Sponsor(s)
We thank Sybille Koch and Sybille Lorenz for sector-field EIMS analysis and Alfredo Ibañez for K D calculations. We gratefully acknowledge the financial support by the Max Planck Society.
Sources of information:
Directorio de Producción Científica
Scopus