Puromycin is one of the
antibiotics interfering with
protein synthesis in the cell by releasing nascent
polypeptide chains before their synthesis is completed. This is because it mimicks Aminoacyl-tRNA, which is normally involved. This is in
prokaryotes as well as
eukaryotes.
A second advantage of its structure is the alpha-amino group, which forms a
covalent bond with the
carboxyl end, causing dissociation from the
ribosome.
H3C CH3
\ /
N
|
C N
// \ / \\
N C CH
| || /
HC C--N
\\ / |
N |
|
O |
HOCH2 / \ |
|/ \|
|\ __ /|
H | |
H-N OH
|
C=O
|
C-CH2-benzene ring-OCH3
|
NH2
Aminoacyl-tRNA looks the same, but with another side chain at the bottom Carbon atom (aka not the benzene ring).