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Penicillin V
(first orally active penicillin)
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 NAM NAG NAM NAG NAM

L-Ala NAM L-Ala

NAG NAM L-Ala
NAG NAM
D-Glu D-Glu D-Glu
L-Ala L-Ala L-Ala
NAM NAG NAM NAG NAM
L-Lys L-Lys L-Lys
D-Glu D-Glu D-Glu
L-Ala L-Ala L-Ala
L-Lys L-Lys L-Lys
D-Glu D-Glu D-Glu

L-Lys L-Lys L-Lys

Bond formation
inhibited by
penicillin

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 D-A la- D -A la
Blocked

HO O

Active Site
OH OH

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Thick porous cell wall

Cell membrane

Cell

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 Hydrophobic barrier
Outer
membrane Porin

Lactamase
L enzymes L
L
Periplasmic
Thin cell wall
space
L

Cell
Cell
membrane

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Fermentation

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Acid or
enzyme

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 Unreactive

X
Folded ring Impossibly
system strained

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Further
reactions

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β-Lactamase
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 O
PEN PEN
PEN
C H
C O CH2 O C OH
C O CH2 O CMe3
O O
O

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Azlocillin

Mezlocillin

Piperacillin

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