Vous êtes sur la page 1sur 249
Contribution `a l’´etude d’oligopeptides ( Caroline Bauchart To cite this version: Caroline Bauchart. Contribution a`

Contribution `a l’´etude d’oligopeptides (

Caroline Bauchart

`a l’´etude d’oligopeptides ( Caroline Bauchart To cite this version: Caroline Bauchart. Contribution a`

To cite this version:

Caroline Bauchart. Contribution a` l’´etude d’oligopeptides (

HAL Id: tel-00688406

Submitted on 17 Apr 2012

HAL is a multi-disciplinary open access archive for the deposit and dissemination of sci- entific research documents, whether they are pub- lished or not. The documents may come from teaching and research institutions in France or abroad, or from public or private research centers.

L’archive ouverte pluridisciplinaire HAL, est destin´ee au d´epˆot et `a la diffusion de documents scientifiques de niveau recherche, publi´es ou non, ´emanant des ´etablissements d’enseignement et de recherche fran¸cais ou ´etrangers, des laboratoires publics ou priv´es.

! " # $% # &! '(() ! " # $ % % #& #
! " #
$% # &! '(()
! " # $
% % #&
# &' * + ,
(
# ) ," , - ,
* +
, *
. /
0
1 2
. " ,
*
. 5 -30 4
1 2 3 4
" #+ #+ 2 6 ,
# #+ #+ 2
- " *
. 7 8
. ," , -
. ,
+" #+ #+ 2
+"
#+ #+ 2
, - . , +" #+ #+ 2 +" #+ #+ 2 #+ #+ & 36

#+ #+ & 36 " 9 + : , $($; < &" = " &" : )>$'' " 4 ? +"& "

(- ( .(- (/ 0

(-( .(-(/ 0

" " +? " ! # ! '((> " #+ #+ & 36 " 9 + : " : 5 11 * 5 0 #+ & , # @0 ,A " " #+ #+ " " @ A "

, 7 + 2 5 & , "! &

5 @ , A " , 7 " 4 B" . 7 +" " & #

, 7 + 7 " 4 B" & " "## " 2 " 5 " : "! 2 , 7 " 3 2 # = " &" : @= " 2 :3 A , / 0 2 # , $($; < &" @ " 1 > " # , A.

7 : & & #? & # & , + " " , " 2 # #+ #+ < &" @ <A2 ," "& ,"

, B 2 +" #+ #+ = " , & 2 +"

# 1 5 #+ 5 &" ? # & & " 11 #"# . 7 & # " # " "# &! & " " :2 # " " # 2 # : # " # " 2 "&& " " " " : & " " 5 " " " " " 1 & " #

# && #" 2 & " & C & ! # " " "

! 2 " # 1 " # 5

& " B 2 & ? " " # "! & # D . 7 " ! " # " " ? " # > " +? D : & &" 1 # " " 5 " #" & .

7 +" & # " , / 0 2 1 # , $($; < &" 2 " "## # D C2 " 5 , " & 2 " " +" < &" " " & 5 " 34 # , 9 3 4 ;$E +C " & & & " 2 ," "& 5 B30" 2 " #+ #+ 6 " F" #+ #+ : "

#+ #+ <2 & " # 1 # " " " " " #

& # ! .

>

" , @ 6 , " A2 & " 1" + G " # " " 2 ," "& 7 8 2 # # " D , $'H> 9 #"& # # #+ " I 1 2 " "## G :"& " # # " " .

" &"D " # " " +? " " C 1" " # & &" 2 " # " #+ 5 , 3 6 " 3 < 3 3 , 9, 2 " #" "# " 1 #" " " & 5 " #+" " " ! . 7 & # #+" & , + + +"&! 2 "! " " & & 36 " 9 + :2 & # "# " " " &! # " " C . " " # 2 " " # " " " C " & ! " " 1" & " &" " & 5 . : " " , 3 6 & " # "! " " # + C ? 2 D #+ #+ " "! " +C 5 , # " # " " 6"# +" &"# , 2 5 " " ! # & &" " " +& & " "! &" " #+" . 7 : & &" " " ! " " & " . " ? " # " " 1 #" 1" ! & # " @J $H(( "A " # & &" < 3 3=3 6 "

# 1 #+" " &" 5 " . 7 & #

#? & C 6" C " 2 " " ," ' 1 " C K 2 " " " " " C " < 3 3=3 6 # "! " " # ," "& D 2 "! " " 1 & , "! & 5 & 36 " 9 + :2 , 7 " 36 " F ," 2 <2 " " C " " " # # ," L C :.

7 " & & # ," "& "! " " C3 B :2 +" #+ #+ #+ #+ < ! @ <A & 3 6 " 9 + :2 2 #+ # <2 & 5

"# " " " #" " " 11 #+" " 3 < .

#

E

7 " & & # & &! 5 # ! 2 ? 2 " " " : & " # " " 2 " # ? & * 3 & " " " 3 " " 1 " #3 3# M 3 , " 7" 5 !" : & " <2 " 1 #+" & # # " 1 ! #+" " M 3 , "& & + &" " # N L , " C

# " & " " @ A

1 " " 1 " # " # " " # "!

# 1 5 1 ! @ ! A 11 # " " 1 " 2 " # @ 6 A M

3 , C " 2 #+ #+ <2 " " " #

, & "

#" + " A2 " 5 , + 4"C G ## " + " &" :2 , + " "1"

: & " & " @ A & 3 6 " 9 + : " " : " &" : M

3 !" 0 2 " " # " 5 <" @ < A = " " 2 " ! # : # < M 3 ," "& " 0 11 ? 2 " < " ! "

: & " " &" :2 " 5 " " " &! : " M 3 ," "& ," < & " & 11 # "

"B " " & + OD "+ " "! " M 3 , "& , " " < & 3 6 " 9 + : & " "## " "! " " " " " " " " C ! & " # 1 " # & "! " & 5 2 " 5 , " # < " ! " # " " C + " # 1 " C ! & M

3 ," "& " ,

+ + 4 " < " "! "

# ? & " " " " #+"

#+ #" " &" : @ #"

" " " #

< &" @ <A " " " 11 # +C C "# " "# "& " :. 7 " &" # " " # &" C& " + ," "& < ? "1" < " ! " # " " #+ #+ &

H

& ! ! " + 5 " # " !" <2 " 5 , "& ," "##" 2 , #+? 0 2 ," 3 + 0"C " "

0 < , "& " 0"#+ " 6 " F " " "

= " " " &" #+ " & " .

" & # , 4 " " 2 #+ # 1 &" 5 <2 & " ? " # " # 1 &" 5 .

7 +" & # " & ," "& + + 6 , " " 1" " & # & +? .

= " <

"## #+" :2 2 ! + & # ! " " "## & & # " " " "&! " # ? " "! C& " + 5 . 7 & # " # ? & , 2 !" 2 " 2 5 2 " 2 + C2 C2 0" !" "2 " 2 &" " , " , ," "& " 0 11 ? 2 " # 5 D " " " &G& ! " <2 C& " + 2 ! "& #" .

7 & # ? #? &

1 2 D : & # & # & " " &

1

& " " :5 D 2 5 & D # "

" & #+ : " & & 11 # " 2 "& 2 2 "

# 1 " # 5 " & "# 1 # 5 " P 1" .

)

1.0 ( (0 , (0 2- - 1. .2/0 ( /. .2/0
1.0 ( (0 ,
(0 2- -
1.
.2/0 (
/.
.2/0

, 1. .2/0 0" #+" .2 +"&! .2 " " , " .2 " "
,
1.
.2/0
0" #+" .2 +"&! .2 " " , " .2 " " C3 B : .2 & .2 ,
,. @3445A. " ! N @ A & # !D #
" " # L . $(( @EA2 $H))3$HQ'.
B
#
0" #+" .2 & .2 +"&! .2 " " , " .2 " " C3 B : .2 C ?
.2 , B ,. @3446A. &" @JH L "A 1 " C3 3 " ! 1 & " .
QE @EA2 )H%3))).
0" #+" .2 " " C3 B : .2 " " , " .2 + &" .2 , B ,.2 & .
" # # " 1 & " "11 # #" " + "
1 & . ! @ A.
0" #+" .2 & .2 +"&! .2 " " , " .2 C ? .2 0 11 ? .2
, B ,. # " ! "# 5 # "
1
#
L 1 + . " @ & A.
0" #+" .2 , B ,.2 +"&! .2 " " , " .2 C ? .2 0 11 ? .2
& . # 1 # " # ! C " #
1 # L ! 1 & " . # ! @ & A.
2--
/.
.2/0
0" #+" .2 & .2 +"&! .2 , B ,. @3447A. ## # 1
& # & & " " # L . $ " % &' " %
( ) " * +,-+. ,//'* 0
12 3* ,.-,4 1 5 3
0" #+" .2 +"&! .2 " " , " .2 " " C3 B : .2 & .2 , B
,. @344 A. " "# " " & # # " 1 ! " ?
&" " # . , " 6 6 7 ! * +8-+4
! 9 ,//.* 1 3* ++' 1 6 6 %% 3
Q

0" #+" .2 & .2 +"&! .2 " " , " .2 " " C3
0" #+" .2 & .2 +"&! .2 " " , " .2 " " C3 B : .2 C ?
.2 , B ,. @3446A. " "# " " #" .
6 :) ; < 6* &/-&+ ,//=*
- 1 3 1 6 6 3
0" #+" .2 " " C3 B : .2 .2 0 11 ? .2 " " , " .2 + &" .2
,
B ,.2 . &
@3446A. 0 " " "! C 1 #" 1 & ! 1 & " & 3
. $ " % ., > " % " *
+&-+? " ,//=* ; 1> 3* 8++-8+, 1 5 $ 3
%
(8. .2/0
(8.
.2/0

69

(8. .2/0 # "& ! # "& 5 # "& " : BC& # "
(8.
.2/0
# "& !
# "& 5
# "& " :
BC& # "
#
+ +"
&
# ! # 5 & "
+ +"
R3 <
R3#C"
3E3+C :C# "& 5
" + +
,
" &"#
"
0
& & ! &
"
"
# "C "
4
> <
4 C# " +C 3>3 + +" +C "
4
3$
4 #" 3 L $
4 6
4 N + " 1"#
H(
+ ! # # " H(S
"
L "
O "
O <
<C :C " &
N3 C
&9
," 9 &
&9B
," 9#+"
,
," :3" " 3 "
,
9,
# & &" " &
" # " " C
# #+ 5
+ + # "
$
" $
;

69

3< , < 6 4 6 6 9 3# " #+ " + &" "
3<
,
<
6
4
6
6
9
3# "
#+
"
+ &" " + 5 +" +"
" " " & C
" C +C "
# 1 " #C 5
" "# " :C " "
# #+ "# 5
! 1
# 1 "# 5
"# " 3 "
& 1 1 +
&
1 &" #
& 9 &
$(

02-- . (

02-- . (

./ 2 .2/ 9(/( 1(

$)

( ( . 1.29 , .: (

$%

.; 1(0 ,(, . (0 .2 .<0

$%

$. 11 +C 5

$%

 

$.$.

11

C ?& 1

$%

$.$.$. " "

$;

$.$.'. , " "! &

'(

$.'. 11 && & "

'$

$.>. 11 " & # !

''

$.E. 11 C ?& #" " # "

'>

$.E.$. 11 " + &! 5

'>

$.E.'. 11 " +C

'E

$.H.

11

C ?& :

'H

$.). 11

 

')

$.Q. = 5 & " # 5 " " 1

')

'. ? 5 " & #

'%

'.$. +

'%

'.$.$. "# ! 5 +

'%

'.$.'. & "! & +

';

'.'. " +

';

'.'.$. "# ! 5 " +

>(

'.'.'. & "! & " +

>$

>. , 1 # "

>$

E. , # #

>$

 

E.$.

#

" 1 & "

>'

E.'. # " "D

>'

E.>. <C C

 

>>

 

$$

; , 2 .2/ ( ,(, . (0 2 0 ( 1 = 21=0( .9(0
;
, 2 .2/ ( ,(, . (0 2 0 ( 1 = 21=0( .9(0 .8( >>
$. " ! ##"
'. " " 5
>. " "
>.$. <C C " BC& " # " 5
>.'. <C C " " "
>.>. K " & # 1 "
>.E. " # +C C
>.H. ?
>E
>E
>H
>H
>)
>Q
>Q
>%
;
1 02 , .2/ (0 ,(, . (0 /0 1 ./ (0 ./ 9 (1( ;;;;;;;;;;;;;;;;;;;;;;;;>?
$. G
'. "! "
'.$. ! " " # "
'.$.$. " & &! " "
'.$.$.$. " " # " & &! " " #"
3 $
3 30
>;
E(
E$
E$
E$
E$
E>
'.$.$.'. " " # " & &! " !" " "
'.$.'. ! " " #C
'.$.>. " #C
E>
EE
EE
'.'.
!
" " "# "
#+ B T+ &&
EH
'.>.
!
E)
.8; (8(/. (0 ,(, . (0 , (0 02 , .2/ ./ (0 ./ 1( ;;;;;;;;;;;;;;;;;75
$. <C C " &" 5
'. ? & "
>. " "
EQ
E%
E%
8; 1( - 0 1( ( 1 8. / ($ 02 (0 ( ,(, . (0 ;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;7@
$. & # 5 5
$.$. " & 1 #
$.'. #
$.'.$. # D # 1
E;
E;
H$
H$
$'

$.'.'. &C 1 "& " " # #C 5 H' $.'.>. H> $.'.E. BC&
$.'.'.
&C 1 "& " " #
#C 5
H'
$.'.>.
H>
$.'.E. BC& & "! & 5 : 1 #"
H>
HE
'. " " 1 &" & # " G # &&
'.$. +" # # T & # "
'.'. " &" " @! A 1 "U#+ @ A
'.>. & 1 #" 5 " ? " "
'.E. & #" & " C
'.E.$. #" "V
'.E.'. #" +
'.E.>. " &
'.E.E. #" "
'.E.H. ! # 11 C ?& C 5
'.E.). & #" & 3 BC&" 5 " C
'.H. " #
>. 4 " " # # #+ 5
>.$. " &" " T " " " "#
>.'. " #
HE
HH
HH
HH
H)
HQ
HQ
HQ
HQ
H%
H%
H;
)(
)(
)$
( ( (A,( .-(/ 1( ;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;63
./ 2 .2/ ;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;63
.; -.0(0 ,2./ -( 2 2129.: (0 ;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;67
$. : "#
$.$. #
$.'. + : T" # "
'. " " " 3<
'.$. #
'.'. + : " #
>. " "# " 1 #" " # & &"
>.$. # "
)E
)E
)H
))
))
))
)Q
)Q
$>

>.'. , 3 6 >.'.$. # >.'.'. & " # " " C >.>. "
>.'. , 3 6
>.'.$. #
>.'.'. & " # " " C
>.>. " 3 3 , 9, " 3< 3 3 , 9,
>.>.$. #
>.>.'. & " # T" " C
>.E. < 3 3=3 6
>.E.$. #
>.E.'. & " # T" " C
)Q
)Q
)%
);
);
Q(
Q(
Q(
Q$
;
( ( (0 ,(, . (0 /0 1 1.-(/ ;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;5>
#
# " : "
" # & & "
! #" W$
! #" W'
# "
Q>
QE
QE
QQ
%H
;H
;
( ( (0 ,(, . (0 2 .9./( 1.-(/ . ( 9(/( (0 , 1
.9(0 .2/ (0 , 2 (./(0 ( 1 . ( ( ( 1 8. / ( 28./( ;;;@5
#
# " : "
" # & & "
! #" W>
! #" WE
# "
;Q
;%
;;
$($
$$$
$'>
.8; ( ( ( 1 02 , .2/ (0 ,(, . (0;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;B36
#
# " : "
! #" WH
# "
$')
$'Q
$';
$E'
$E

.0 00.2/ <./ 1( ( ,( 0,( .8(0;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;B77 (<( (/ (0 . 1.29 , .:
.0 00.2/ <./ 1( ( ,( 0,( .8(0;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;B77
(<( (/ (0 . 1.29 , .: (0;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;B7@
//(A(0;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;B57
! B ) & # " 1 & #+ & 5 "# "&
$QE

! 3 ) " & " @J H L "A 1 " " 3< 3 3 , 9, " " # @ X EA # # " > & ? + " ? #+" # " ! # @1" :31 2 " # "

$Q)

1

! > ) ? @J H L "A 1 " " 3< 3 3

, 9, " # " : # 5 : #" 2 " D D " 2 # # " > & ? + " ? " & "

$Q;

$H

./ 2 .2/ 9(/( 1(

> "6 6

" " # " " & " + &" . 11 2 " "! " # " " & # 2 5 ! "# "& "! 1 ! 2 # +" " . 1 2 T G " & " & !"! & " & " T"# "& . 11 2 " & 2 " # " " : & 2 5 # " T+C C ? "# ! 5 " " " + &" " &" 1 11 " : T " & * ! 1 @ " " A2 C ?& && "

@ && 3 & " A2 C ?& : # " @" # & "# # & & " A # C ?& #" " # " @" +C 2 " + &! 5 A. "

" 2 " #+ #+ "# ! 5

! "# 1

" & " # G # " " 11 " " ! 3G . " 2 T " 2 T # " " " 2 3G " # 5 1 ? # # T "

T : "# 1 "# & # && # " T" " 2 1" " " " " T " & 1 #

# & & & " & " . " 2 " " "

" # # " & " "! ! "# 1 1" # ! T" 5 5 " #" T" & " "# . 1 # T : # # # & " & # # " # " 1 &" & # " & 9 " . T " " # " # " #+ #+ #

T # 11 " T " " & #" . : & "# 2 # # & G 5 " 11 " " "# 2 #T 3 3 " "# 1 " " G " # ! . T # " & 5 T !Y " " #+ #+ # +? 5 " T" & 5 " " G # ! "# 1 . ! "# 1 " " " & ? " # " " 5 # " & " # . ? # " " # "#

# # " &! : 11 +C 5 #" "# 5 2 "

# & & 5 # " & " . 2

T & " # # " + &? 1 2 5 # T+C C