Background: Vaccine efficacy depends significantly on the use of appropriate adjuvant(s) in the formulation. Phytol, a dietary diterpene alcohol, is similar in structure to naturally occurring isoprenoid adjuvants; but little is known of its adjuvanticity. In this report, we describe the relative safety and efficacy of phytol and its hydrogenated derivative PHIS-01 compared to commercial adjuvants.
A kinetic isotope effect (KIE) experiment
is described for the
physical chemistry laboratory. Students conduct a hypochlorite (household
bleach) oxidation of an equimolar mixture of 1-phenylethanol and 1-deuterio-1-phenylethanol
to acetophenone. The reaction occurs in a biphasic reaction mixture
and follows first-order kinetics with respect to either isotopomer
of 1-phenylethanol. Reaction progress is measured by gas chromatography–mass
spectrometry (GC–MS). Alternatively, the experiment could be
conducted with each isotopomer serially and followed by GC alone.
The reaction rate constant for the disappearance of 1-phenylethanol, k
H, ranges from 3 × 10–4 to 2 × 10–3 s–1, while
kD, for 1-deuterio-1-phenylethanol, ranges from 9 ×
10–5 to 5 × 10–4 s–1. The observed KIE, the ratio k
H/k
D, is remarkably robust, ranging between 2.3
and 3.6, with a mean of 2.9 and standard deviation of 0.4 over three
years of student data. The robustness of the observed KIE stems from
using competing reactions. The experiment can be completed in about
3 h; GC–MS data is conveniently acquired overnight using an
autosampler. The experiment, as presented here, can stand alone, but
is well-suited to cross-course collaboration between the organic and
physical chemistry laboratories. The preceding companion paper describes
the synthesis of 1-phenylethanol and 1-deuterio-1-phenylethanol using
borohydride or borodeuteride reduction of acetophenone as an experiment
for the organic laboratory.
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