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Structure mimicking the conformation of oxycarbenium species.
O
HO
NH
OH
O
OH
O
O
Chem. Commun.
2004, 1216.
P
P
N
O
HO
O
O
O
OH
HO
7
OH
OH
O
OH
Bioorg. Med. Chem. Lett.
2006,
16,
1123.
O
Potent intermediates
8
HO
OH
O
Potent inihbitors
NH
OH
O
OH
O
H
OH
O
O
O
P
P
N
HO
H
P
UMP
O
OH
O
OH
OH
O
O
O
O
9
10
HO
Tetrahedron Lett.
2007,
48
,4353.
Tetrahedron
2007,
63,
2070.
OH
OH
OH
O
NH
O
H
2
N
HO
O
P
O
N
O
O
OH
HO
J. Org. Chem.
2006,
71
,7337.
OH
11
HO
OH
OH
HO
O
H
HO
X
OSO
3
X=S:
Carbohydr . Res.
2004,
339
,401.
X=NH:
Carbohydr. Res.
2004,
339
,2205.
12
HO
OH
HO
Fig. 2 Examples of molecular tools designed for the study of UGM enzyme.
during the past two decades as inhibitors of the flavoenzyme
UGM.
32,33,39,43,51,54,55,64-68
Once again, this non-exhaustive list of
inhibitors is complemented each day through the scientific literature.
Many of them are directed towards bactericide effect against M.
tuberculosis. But another important consequence of this fascinating story
is that discovery of other mutases has been significantly accelerated, for
instance for Aspergillus fungi,
60
Campylobacter,
61
Klebsiella species,
69
and
nematodes.
58
3 Furanosyl conjugates and transferases and
polymerases
The investigations towards furanosyl transferases was driven by the huge
progress made on the comprehension of the biological pathways involved
in the biosynthesis of arabinogalactan, the structural polysaccharide ex-
pressed at the surface of M. tuberculosis cell wall. Consequently, this part
focuses on discoveries made in this field.
3.1 Structure of the cell wall membrane of Mycobacterium
tuberculosis
Furanosyl transferases require 1-phospho-polyprenyl-furanosides or
nucleotide-furanoses as donors. The group of Besra has reinvestigated
the synthesis of monophosphodiester 1 (Fig. 1) in 1995 starting from
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