Synthesis, analysis and rearrangement of novel unnatural glucosinolates.
As part of a structure activity study to examine the interaction of glucosinolates with leaf surfaces, a number of glucosinolates were synthesised bearing novel side chain functionalities. These included 7-carboxyheptyl, heptyl, and naphthyl side chains. For the carboxyheptyl glucosinolate, a novel intramolecular rearrangement reaction was observed during the final deprotection step, which generated an ester attached to the C-3 of glucose. Studies by 1H NMR spectroscopy showed that the hydrophobic side chain associated with one face of the glucose ring and it was proposed that this was the driving force for the rearrangement. Similar hydrophobic interactions were also observed between the heptyl and naphthyl side chains and the glucose.
Davidson
N E
NE
School of Chemistry, University of St. Andrews, Fife, UK.
Rutherford
T J
TJ
Botting
N P
NP
D002236:Carbohydrate Conformation; D005947:Glucose / Q000737:chemistry; D005961:Glucosinolates / Q000138:chemical synthesis* / Q000737:chemistry; D006859:Hydrogen; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D013329:Structure-Activity Relationship
D005961:Glucosinolates; D007202:Indicators and Reagents; D006859:Hydrogen; D005947:Glucose