00:00
Right, identifying an enantiomer, is problematic
and the reason for this being that, with the
exception of the biological interactions that
I showed you earlier on, where one will give
rise to one biological response and one
enantiomer will give rise to another biological
response, there are chemically and physically
no real differences between the two. They
would boil at the same temperature, they will
melt at the same temperature, they will undergo
the same reactions and this is problematic.
00:30
However, as I said before, enantiomers
can rotate the plane of polarised light in
equal degrees, at opposite directions. Also
as I said, the enantiomer which rotates the
plane of polarized light to the right is given
the denotation of plus, and the enantiomer
which rotates the plane of polarized light
to the left is given the designation minus.
00:56
Bear in mind, and I do stress this because
it can get confusing. This is an experimental
observation of what an individual molecule
does to the plane of polarised light. Plus
means it rotates it to the right, negative
means it rotates it to the left. But there
is no correlation between what is experimentally
observed, and what we have just assigned under
Cahn-Ingle-Prelog Rules. So you can actually
have something which you designate as being
rectus which actually rotates the plane of
polarised light to the left. It’s counterintuitive,
but it is something you need to be aware of.
A racemic mixture, i.e. a mixture containing
two enantiomers, equal concentrations, will
not rotate the plane of polarized light at
all. They will cancel each other out.
01:46
Something else to bear in mind, and this has
been exploited on several occasions from a
medical perspective. When trying to isolate
one particular enantiomer from a mixture,
from racemate, and that is that enantiomers
react differently with other chiral compounds,
mostly because they form diastereomers as
we will see. This and the other ways of doing
it, also consider for example, separation of
chiral molecules on a chiral column, but this
can be quite expensive. And now I want to
draw your attention to the idea of asymmetric
synthesis. As I said before because chemically
and physically two enantiomers will have a
similar properties, it is very difficult to
separate them. Possible by reacting them with
other chiral molecules where the diastereomers
will have different physical and chemical
properties. But there is another way of doing
it, and this is where I want to draw your
attention to some Nobel prize winners for
this particular area. One of them William
S. Knowles, who came up with the enantiomeric
selective synthesis of levodopa used in the
treatment of Parkinson’s Disease. Also,
Ryoji Noyori responsible for the enantiomeric
selective synthesis of carbapenem. Carbapenem
is a very important beta-lactam based antibiotic
as you may be aware. In fact it is one of
the broadest spectrum of all of the beta-lactam
antibiotics and is generally considered the
last line of defense in the treatment of gram
negative bacterial infection.
03:20
And finally Prof. Barry Sharpless who used
the first asymmetric catalysis synthesis for
the development of Paclitaxel which is a very
important anticancer drug.