W0 2011/000721 A1 I||||||||||||||||||||||||||||||||||||||||||||||||||||||||| - Questel

oom temperature for 2 days. MALDI mass analysis of a sample of the reaction
mixture showed the completion of the reaction.
The reaction mixture was diluted in methanol and charged directly onto a LH-
20 Sephadex column in methanol. Slow elution led to the purification of the
product 15 that was isolated in good yield (25.5 mg, 88% yield).
1 H-NMR (400 MHz, D2 O) δ (ppm): 5.00 (s, H I M -). 4.84 (s, H 1M ), 4.40-4.10 (m,
OCH 2 CH 2 N 3 , CH 2 O a, CH 2 O b, CH 2 O c), 4.04 (s, D 2 ), 3.97 (bs, H 2M ), 3.92 (s,
H 2 M), 3.89-3.53 (m, H 3 M', β β, H M Θ. D I , H wA. H MA. H 3 M, H4M, H 4
, H 7 , H 5 M,
H 5M C H 2 N 3 ), 3.69 (s, COOCH 3 ), 3.68 (s, COOCH 3 ), 3.49-3.34 (m, 8H, H 8 ),
3.00-2.85 (m, D 4 , D 5 ), 2.73-2.59 (m, CH 2 COO), 2.59-2.46 (m, CH 2 CONH),
2.27-2.03 (m, D 6eq , D 3θq ), 1.89-1 .71 (m, D 6ax , D 3ax ), 1.40-1 .15 (m, CH 3 a\ CH 3 D,
CH 3 C'). 13 C-NMR (100 MHz, D 2 O) δ (ppm): 177.3, 177.0, 173.5, 173.0, 98.7,
74.7, 73.5, 72.2, 71.0, 70.9, 70.7, 70.6, 70.1, 68.2, 67.1, 66.9, 66.2, 65.4, 61.1,
52.6, 46.4, 39.1 , 39.0, 39.0, 30.1, 29.2, 27.2, 26.9, 17.3. MS (MALDI, matrix:
SIN): distribution centered on 30 sugar loaded, for 32 sugars [M+Na] +
calculated: 25222.75, found: 25227.9.
EXAMPLE 4
Infection Studies
B-THP-1/DC-SIGN cells are derived from B-THP-1 human B cell line by
transfection of DC-SIGN expression vector in order to express high levels of
the DC-SIGN receptor. This cell line supports efficient DC-SIGN mediated HIV
transmission and is a wide-used model system to mimic HIV capture and
transmission to T-lymphocytes by dendritic cells (see, as a general reference,
Geijtenbeek, T.B.H.; Torensma, R.; Van Vliet, S.J.; van Duijnhoven, G .C.F.;
Adema, G.J:; van Kooyk, Y.; Figdor, CG. Ce//, 2000, 100, 575- 585). B-THP-
1/DC-SIGN cells were preincubated for 30 minutes either in the presence or in
the absence of the DC-SIGN inhibitors prior to 3 hours exposure to the virus