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Cell membrane
Bioorthogonal
labeling
N
3
O
O
(b)
O
O
P
S
O
O
OH
O
C
13
H
27
O
N
O
OO
S
O
P
O
O
C
13
H
27
O R
1
N
30
O
O
Biosynthetic
Incorporation
32
O
R
2
O
HN
C
15
H
31
O
O
C
13
H
27
O
P
O
C
13
H
27
O
N
O
P
O
O
C
13
H
27
N
O
OH
O
O
31
33
O
29a-c
O
O
O
a
:R
1
=O,R
2
=
8
P
O
O
O
O
O
NH
3
14
b
:R
1
=H
2
,R
2
=
O
5
c
:R
1
=O,R
2
=
34
O
5
FIGURE 4.8
Strategies for
in situ
labeling of tagged lipid analogs. (a) Cartoon depicting bioorthogonal labeling of lipids in
complex environment. (b) Structures that have been developed for
in situ
labeling studies. (See color plate section.)
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