Biomedical Engineering Reference
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OH
1. H
3
PO
3
2. HCHO
OH
O
O
O
O
O
HO
HO
NHCH
2
PO
2
H
2
N(CH
2
PO
2
H
2
)
2
N-Methylenephosphonic chitosan
O
H
O
OR
OR
P
H
P
OR
OH
O
O
O
O
O
HCHO
O
HO
HO
NH
R = H, OEt
NH
2
OR
P
OR
O
N-Methylenephosphonic chitosan
P
2
O
2
, MeSO
3
H
Phosphorylated chitosan
OPC
O
O
Cl
O
O
-
O
P
O
PCO
O
N
+
P
O
PC
O
N
PC
PC
Phosphorylcholine chitosan
O
O
P
CH
2
N
•
O
OO
XH
2
C
O
O
CH
3
N
•
O
P
R(N)
•
n-2
CH
2
OO
O
-
O
OH
n
OH
O
OH
OH
P
O
O
HO
O
NH
2
H
3
PO
4
, Urea
O
O
DMF, 150°C
O
O
O
P
NHR
HO
OH
OH
OH
HO
O
-
O
O
O
O
NHCOHCH
3
O
CH
3
CH
3
O
•
O
N
•
HO
HO
y
z
OO
P
CH
3
HO
x
NH
O
O
NH
2
H
O
O
-
O
H
3
CN
•
CH
3
CH
3
O
OH
OH
P
O
H
3
P
4
,
Et
3
PO
4
, P
2
O
5
O
O
Hexanol, 35°C
O
O
O
P
NH
PO
HO
OH
HO
OH
Phosphorylated chitosan
OR
1
O
O
ClCH
2
CH
2
P(O)(OH)
2
R
1
O
O
50% KOH/CH
3
OH
NH
2
R
1
= CH
2
CH
2
P(O)(OH)
2
Chitosan-O-ethyl phosphonate
OR
1
O
O
ClP(O)(OCH
2
CH
3
)
2
O
R
1
O
45% NaOH
NH
2
R
1
= P(O)(OCH
2
CH
3
)
2
Chitosan alkyl phosphonate
Figure 2.16
Synthesis of phosphorylated chitosan.
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