132
4, Nitrogenous Compounds
OMe
OMe
Br
Br
B
R
\À/Br
RO
OR
I
H
H
I
CH 2 —C—CON—(CH 2 ) 4 —Ν—CO—C—CH 2
II
II
NOR
NOR
46
a: R = Η
b: R = Me
OMe
Br^^A^Rr
MeO^^P
CH 2 —C—C0 2 H
II
NOMe
47
From the mother liquors of aerothionin (45) Fattorusso et al. (1971a)
isolated a homolog, homoaerothionin (48), the structure of which was
established in full analogy with that of aerothionin. A full account of this
work is available (Moody et al, 1972).
OMe
OMe
OH
B
L
*TLF
B R
ΒΓ
^^γ
ΒΓ
Br^C/Br
HO
>(
>^OH
\^
or Ν
{ Ο
I
\
/
\
/
CH 2 —CH—C0 2 H
Ν =4
Η
Η
>=N
Ι
CON—(CH 2 ) 5 —Ν—CO
X
NH 2
48
49
Fattorusso and co-workers suggest that the aerothionins (as well as
aeroplysinin-1) are biosynthesized from a derivative of 3,5-dibromotyrosine
(49), which condenses with an appropriate α,ω-diaminoalkane derived from
the corresponding amino acids ornithine (19) or lysine (50).
NH 2
I
H 2 N—(CH 2 ) 4 —CH—C0 2 H
50
4, Nitrogenous Compounds
OMe
OMe
Br
Br
B
R
\À/Br
RO
OR
I
H
H
I
CH 2 —C—CON—(CH 2 ) 4 —Ν—CO—C—CH 2
II
II
NOR
NOR
46
a: R = Η
b: R = Me
OMe
Br^^A^Rr
MeO^^P
CH 2 —C—C0 2 H
II
NOMe
47
From the mother liquors of aerothionin (45) Fattorusso et al. (1971a)
isolated a homolog, homoaerothionin (48), the structure of which was
established in full analogy with that of aerothionin. A full account of this
work is available (Moody et al, 1972).
OMe
OMe
OH
B
L
*TLF
B R
ΒΓ
^^γ
ΒΓ
Br^C/Br
HO
>(
>^OH
\^
or Ν
{ Ο
I
\
/
\
/
CH 2 —CH—C0 2 H
Ν =4
Η
Η
>=N
Ι
CON—(CH 2 ) 5 —Ν—CO
X
NH 2
48
49
Fattorusso and co-workers suggest that the aerothionins (as well as
aeroplysinin-1) are biosynthesized from a derivative of 3,5-dibromotyrosine
(49), which condenses with an appropriate α,ω-diaminoalkane derived from
the corresponding amino acids ornithine (19) or lysine (50).
NH 2
I
H 2 N—(CH 2 ) 4 —CH—C0 2 H
50