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Gram negative
acetone
acetone
Norcardiform bacteria
Cell walls of nocardiform bacteria
These include the mycobacteria such as M.
tuberculosis
Nocardiform bacteria are Gm +ve but are difficult to
stain.
Peptidoglycan is covalently linked to the
polysaccharide arabinogalactan.
Lipids are esterified to arabinogalactan and make up
60% of the dry cell weight.
Lipids confer resistance to staining and to antibiotics
and biocides.
Peptidoglycan
The major structural component of GM+v and
GM_ve cell walls consists of repeating
disaccharide unit of 2 different N-acetylated
aminosugars.
Short peptide chains are attached to alternate
aminosugars and these crosslink to one another
via peptide bonds.
Some bacteria have many sheets of
peptidoglycan and these are joined by the same
type of crosslink
N-acetylglucosamine
N-acetylmuramic acid
L-alanine
D-glutamic acid
Meso-diaminopimelic acid
D-alanine
Transpeptidation
Crosslinks are formed by a transpeptidation reaction, catalysed by a
membrae-bound transpeptidase.
Carboxypeptidase
One of a number of other enzymes in the
cell membrane that acts on cell wall
synthesis.
-Lactam Antibiotics
Penicillins c. 1940s
Cephalosporins c. 1960s
Carbapenems c. 1990s
ALL CONTAIN LACTAM RING
The Penicillins
Penicillins were discovered by Alexander Fleming in the late
1920s.
Staphylococcus lawn
Zone of inhibition
Fungal growth
The Penicillins
H
N
Ph
O
Developed by Florey
and Chain as part of
the second world war
effort.
N
O
COO -
Biosynthesis of -lactams
Origins
Valine
Cysteine
Structural mimicry of D-ala-D-ala ?
Phenylalanine
Semi-synthetic penicillins
Amoxycillin
Ampicillin
Methicillin
Beta-lactams - cephalosporins
Cephalosporins
Cefaclor second generation
Gram negative activity and
activity against Haemophilus
Other beta-lactams
Carbapenems
Very broad spectrum
Resistant to most
beta-lactamases
Monobactams
Just one so far
Active against Gram
negatives only
Other beta-lactams
Imipenem, an example
of a carbapenem. It
is rapidly deactivated
by the kidneys unless
administered with a
specific inhibitor,
cilastatin.
Aztreonam, the only
monobactam in use at
the moment.
-Lactams
Inhibit cell wall synthesis
Combine the specificity of natural products
with the versatility of laboratory-based
drugs and are incredibly successful as a
result.
Have a heroic and inspiring history that
has informed the development of other
drugs.