27 CH203 Fall 2014 Lecture 27 November 7.pdf
Transcript of 27 CH203 Fall 2014 Lecture 27 November 7.pdf
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6)789 :;8 6; :)78 79 : 9+29*:;)( *=:* ?,/8+)(9 $@7/;9 7; :A+(/+9 9/B+C/;D
6 2:9( 79 : 9+29*:;)( *=:* ?,/8+)(9 E$F7/;9 7; :A+(/+9 9/B+C/;D
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!(B()*,/;9 :9 : 6 9+29*:;)( *=:* 79 : ?,/*/; :))(?*/,D
L=( !(B()*,/;9 /M !F2+*(;( N2:9(O ,(:)* H7*= $
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6)78 :;8 2:9( 9*,(;P*=9
Q
L=( (A+7B72,7+1 (R?,(997/; M/, *=( 8799/)7:C/; /M :;I +;)=:,P(8
:)783 $63
):; 2( H,7S(; :9 : ,:C/ /M *=( )/;)(;*,:C/;9 /M *=( ?,/8+)*9
87078(8 2I *=( )/;)(;*,:C/;9 /M *=( ,(:)*:;*9
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6)78 :;8 2:9( 9*,(;P*=9
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L=( (A+7B72,7+1 )/;9*:;*3 !(A3 /M *=( 7/;7T:C/; /M :)78 $6 7; H:*(,
*:U(9 *=( M/,1
V:*(, :9 : 9/B0(;* 79 ?,(9(;* 7; : )/;9*:;* )/;)(;*,:C/; /M :2/+*
KKDK 1/BW'D X+BC?B7):C/; /M 2/*= 978(9 2I *=:* )/;9*:;* P70(9 :
;(H A+:;C*I3 !:3 *=( :)78 8799/)7:C/; )/;9*:;*D
HA H
2
O
[H
3
O
][A
]
[HA][H
2
O]
eq
A
H
3
O
=
eq
[H
2
O]
Ka
[H
3
O
][A
]
[HA]
= =
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6)78 :;8 2:9( 9*,(;P*=9
]
?!:[ FB/P4%!:
$I8,/)=B/,7) :)78 =:9 : ?!:[ F- 9/
!:[ 4%-[
$I8,/)=B/,7) :)78 7; H:*(, 79 7/;7T(8D \* 79 : 9*,/;P :)78D
H
O+
H
H
Cl-
HCl
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6)78 :;8 2:9( 9*,(;P*=9
4%
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6)78 :;8 2:9( 9*,(;P*=9
44
\M *=( ?!: ^ %3 *=(; !: _ 4 N9*,/;P :)78O
\M *=( ?!: ` %3 *=(; !: ` 4
\M *=( ?!: _ %3 *=(; !: ^ 4 NH(:U :)78O
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E2*:7;7;P !(AM,/1 !:
4!
a/, *=( :)78F2:9( ,(:)C/;
$6 @ < 6F@ $
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E2*:7;7;P !(AM,/1 !:
4&
?!(A[ ?!$6b?!$
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617;/ :)789
45
H2N
OH
OH2O
L-Valine;(S)-Valine
+H3N
O-
O
L-Valine zwitterion
6* ?$ 0:B+(9 =7P=(, *=:; *=( ?c: /M *=( ):,2/RIB7) :)78 P,/+? N1(:; M/, *=( !% )/11/;
:17;/ :)789 79 :2/+* !D!O3 *=( ;(P:C0( ):,2/RIB:*( 7/; ?,(8/17;:*(9D 6* ?$ 0:B+(9 B/H(,
*=:; *=( ?c: /M *=( dF:11/;7+1 P,/+? N1(:; M/, *=( !% )/11/; dF:17;/ :)789 79 :2/+*
]D5O3 *=( ;7*,/P(; 79 ?,(8/17;:;*BI ?,/*/;:*(8D 6* : ?$ 2(*H((; !D! :;8 ]D53 dF:17;/
:)789 )/;979* /M *=( ;(P:C0(BIF)=:,P(8 ):,2/RIB:*( P,/+? :;8 *=( ?/97C0(BIF)=:,P(8 dF:11/;7+1 P,/+? :;8 =:0( : ;(* )=:,P( /M T(,/D L=79 1/B()+B:, 9*:*( 79 U;/H; :9 :
TH7S(,7/;3 M,/1 *=( e(,1:; !"#$%&1(:;7;P #$%&'(D
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617;/ :)789
4K
6 C*,:C/; )+,0( /M :; :17;/
:)78 ,(0(:B9 *=( ?$ :* H=7)=
*=( ;(* )=:,P( /; *=(
1/B()+B( 79 T(,/D L=79 ?$ 79
8(J;(8 :9 *=( 79/(B()*,7)
?/7;* N?\OD
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?$ ') *'*+
4Y
j*:+,/9?/,7;(3 79/B:*(8 7; 4]-- M,/1 *=( 2:)*(,7+1 j*,(?*/1I)(9 9*:+,/9?/,(+9D L=(2:)*(,7+1 9I;*=(97T(9 9*:+,/9?/,7;( :9 :; :;CM+;P:BD j*:+,/9?/,7;( 79 :; 7;=727*/, /M :
2,/:8 9?()*,+1 /M ?,/*(7; U7;:9(9D L=( 7;=727C/; ?/*(;)I 79 9*,/;P(9* M/, ?,/*(7; U7;:9(
# Nkc#OD j*:+,/9?/,7;( (R=727*9 : 9*,/;P )I*/*/R7)7*I */ 9/1( 1:11:B7:; *+1/, )(BB
B7;(9 :;8 7;8+)(9 )(BB :?/?*/979D
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?$ ') *'*+
4]
9 8 7 6 5 4 3 2 1 ppm
0.97
3.1
6
1.2
3
3.17
1.1
9
3.3
0
1.0
6
2.0
3
1.0
4
2.1
3
2.2
0
1.0
8
2.07
0.9
8
1.0
0
NN
HN
O
H3CO NHCH3
O
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?$ ') *'*+
!%
N N
HN
O
O
HN
O
CH3CH3
Aromatic halogenation
N-demethylation
O-demethylation
H3C
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?$ ') *'*+
!4
N N
HN
O
O
N+
O
CH3CH3
N N
HN
O
O
N+
O
CH3CH3T3C
CT3
HH
[Methyl-3H]N,N-Dimethylstaurosporine
H3C H3C
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?$ ') *'*+
!!
Kd=unbound ligand x empty receptor
ligand-receptor complex
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?$ ') *'*+
!&
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L=(,1/)=(179*,I
!5