Chemistry Reference
In-Depth Information
persilylated
D
-Araf.
70
After selective anomeric deprotection, the resulting
hemiacetal afforded 1 thanks to the phosphoramidite approach followed
by desilylation. The authors showed that compounds 1 with C
50
or C
55
chain length were much more active with mycobacterial Araf transferase
than the corresponding C
10
analogues.
71
Chatterjee and coworkers
established on their side that transfer of the first Araf part to the galactan
backbone of Mycobacterium smegmatis is essential to the growth of
the microorganism.
72
The final arabinogalactan contains approximately
70
D
-Araf monomers.
73
Considering the Galf part of the arabinogalactan polysaccharide
produced by M. tuberculosis
74,75
(Fig. 3), the biosynthesis begin with
connection of a N-acetyl-a-
D
-glucosamine-1-phosphate (a-
D
-GlcNAcp-1-P)
residue to a decaprenyl phosphate chain, anchored into the biological
OH
O
HO
O
Ac
NH
O
O
O
Me
HO
O
O
O
P
O
P
Decaprenyl
HO
OH
O
13
UGM
UDP-
α
-D-Gal
p
UDP-
α
-D-Gal
f
OH
GlfT1
O
HO
UDP
O
O
O
Ac
NH
O
Me
O
O
O
O
P
O
P
Decaprenyl
HO
O
HO
14
OH
O
HO
UDP-
α
-
D-
Gal
f
OH
GlfT1
OH
HO
O
UDP
HO
O
Ac
NH
O
O
O
Me
O
O
O
O
P
O
P
Decaprenyl
HO
O
HO
OH
O
15
O
HO
O
UDP-
α
-D-Gal
f
OH
OH
GlfT2
HO
OH
OH
UDP
HO
O
HO
O
Ac
NH
O
O
O
Me
O
O
O
O
P
O
P
Decaprenyl
HO
O
HO
OH
O
O
HO
16
O
OH
UDP-
-D-Gal
f
α
OH
HO
GlfT2
OH
OH
UDP
O
HO
O
O
HO
O
HO
Ac
NH
O
O
Me
O
OH
O
O
O
O
P
P
O
Decaprenyl
HO
HO
O
HO
OH
O
17
O
HO
O
OH
OH
HO
OH
O
HO
6-30
O
O
HO
O
OH
OH
HO
OH
HO
Fig. 3 Chemical structure of the galactan found in M. tuberculosis cell wall.
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