TABLE 11.1 (
Continued
)
Metabolic reaction
Description
Molecular formulachange
m
/z
change
R–CO–R
0!
R–CHOH–R
0
Ketone to alcohol
+H
2
2.0157
R–CH
–R 2
0!
R–C(O)–R
0
Methylene to ketone
–H
+ O 2
13.9792
Hydroxylation and desaturation
Hydroxylation and desaturation
–H
+ O 2
13.9792
R–XH
!
R–X–CH
3
(X = N, O, S)
N, O, S methylation
+CH
2
14.0157
R–CH
CH 2
3
!
R–COOH
Ethyl to carboxylic acid
–CH
+O 4
2
15.9586
R–H
!
R–OH
Hydroxylation
+O
15.9949
R–NH–R
0!
R–NOH–R
0 ;RR
0 RN
!
RR
0 R
0 NO
Second/third amine to
hydroxylamine/
N
-oxide
+O
15.9949
R–S–R
0!
R–SO–R
0 ; R–SO–R
0!
R–(O)S(O)–R
0
Thioether to sulfoxide,
sulfoxide to sulfone
+O
15.9949
R–CH = CH–R
0!
R–CH(O)CH–R
0
Aromatic ring to arene
oxide
+O
15.9949
R–CH
CH 2
3
!
R–CH–(OH)
2
Demethylation and two
hydroxylation
–CH
+O 2
2
17.9741
R–CH = CH–R
!
R–CH
–CHOH–R 2
0
Hydration, hydrolysis
(internal)
+H
O 2
18.0106
R–CN
!
R–CONH
2
Hydrolysis of aromatic
nitriles
+H
O 2
18.0106
Hydroxylation and ketone formation
Hydroxylation and ketone
formation
–H
+O 2
2
29.9741
C
Hn
m
!
C
Hn
m-2
O
2
Quinine formation
–H
+O 2
2
29.9741
R–CH
! 3
R–COOH
Methyl to carboxylation
–H
+O 2
2
29.9741
R–H
!
R–O–CH
3
Hydroxylation and
methylation
+CH
O 2
30.0105
2
hydroxylation
2
hydroxylation
+O
2
31.9898
RR
0 S
!
RR
0 SO
2
Thioether to sulfone
+O
2
31.9898
R–CH = CH–R
0!
R–CH(OH)–CH(OH)–R
0
Alkenes to dihydrodiols
+H
O 2
2
34.0054
R–NH
! 2
R–NHCOCH
3
Acetylation
+C
H 2
O 2
42.0106
3
hydroxylation
3
hydroxylation
+O
3
47.9847
R–SH
!
R–SO
H 3
Aromatic thiols to
sulfonic acids
+O
3
47.9847(continued
)
333