Chemistry Reference
In-Depth Information
O
N
3
R
N
H
3
R = primary or aryl amine
GDP
CuSO
4
/ Cu wire
EtOH: H
2
O:
t
BuOH (2:3:5)
O
N
NH
O
O
O
N
O
P
O
O
P
O
N
NH
2
O
N
NH
O
O
N
N
HO OH
55
SCHEME 13.11
Synthesis of
-1,3-fucosyltransferase VI (Fuc-T VI) inhibitor
55
by Cu(I)
conditions.
mannose-containing surface glycoconjugates by elongating short mannose oligosac-
charides, with or without the cyclic phosphate, through the addition of
-1,2-linked
mannosyl residues. In order to determine the substrate tolerance and, consequently,
the active-site architecture of the
Leishmania
-1,2-mannosyltransferases, the click
chemistry approach was used to construct a library comprising 28 mannose derivatives
from the coupling of either an azide or an alkyne-functionalized mannose, such as the
6-azido mannoside
56
and propargyl mannoside
57
, with an alkyne- or azide-based
diversity set, respectively, and screen them directly from reaction mixtures (Scheme
13.12) [41]. Thus, screening of the series against
L. mexicana
-1,2-mannosyl trans-
ferases was performed using radiolabeled GDP-[
3
H]Man as donor. The propargyl
N
3
N
N
variable
region
OH
N
Cu
I
O
H
HO
variable
region
OH
+
O
HO
HO
OMe
OMe
56
OH
OH
OH
OH
O
O
HO
HO
H
HO
N
N
Cu
I
variable
region
variable
region
N
+
N
3
O
O
57
SCHEME 13.12
Synthesis of mannose derivatives by click chemistry approach using azide
56
or alkyne
57
.
Search WWH ::
Custom Search