10120
S. N. Lam et al. / Bioorg. Med. Chem. 16 (2008) 10113–10120
purified using RP-HPLC with a YMC-Pack ODS-AQ column using
10 mM NH4CHO2 and MeOH as eluents. Lyophilization provided
12 as a white powder. 1H NMR (D2O, 500 MHz) d7.27 (d, 2H,
J = 7.7 Hz), 7.23 (d, 2H, J = 7.7 Hz), 7.20 (d, 2H, J = 7.7 Hz), 7.13 (t,
4H, J = 7.7 Hz), 7.05 (d, 2H, J = 8.2 Hz), 6.94 (d, 2H, J = 7.7 Hz),
6.75 (d, 2H, J = 8.2 Hz), 4.55 (m, 1H), 4.40 (m, 2H), 4.34–4.23 (m,
5H), 4.14 (m, 2H), 4.08–3.93 (m, 17H), 3.88 (d, 4H, J = 5.9 Hz),
3.84–3.68 (m, 21H), 3.59 (br s, 21H), 3.39 (t, 2H, J = 4.7 Hz), 3.11–
3.00 (m, 4H), 2.93–2.90 (m, 6H), 2.79 (dd, 1H, J = 6.9 Hz, 17 Hz),
2.68–2.50 (m, 6H), 2.35 (t, 3H, J = 8.1 Hz), 2.18 (t, 2H, J = 7.6 Hz),
2.11–1.87 (m, 14H), 1.76 (m, 1H), 1.70–1.64 (m, 3H). 1.33 (m,
4H), 1.11 (br d, 7H, J = 6.2 Hz), 1.01 (m, 2H), 0.86 (d, 10H,
J = 6.7 Hz), 0.79 (t, 6H, J = 7.3 Hz), 0.75–0.70 (m, 8H), 0.66 (d, 3H,
J = 6.7 Hz). 13C NMR (D2O, 150 MHz) d178.53, 178.32, 178.25,
174.89, 174.73, 174.51, 174.16, 174.07, 173.99, 173.92, 173.61,
173.52, 173.40, 173.28, 173.14, 172.59, 172.53, 172.01, 169.20,
155.25, 136.55, 136.43, 131.26, 130.02, 129.90, 129.83, 129.21,
128.81, 128.11, 126.15, 125.95, 125.11, 118.21, 117.60, 116.25,
115.17, 114.31, 111.35, 110.51, 107.39, 105.36, 102.91, 102.68,
100.77, 100.70, 100.64, 98.01, 70.77, 70.32, 70.26, 70.22, 69.91,
67.72, 64.39, 61.78, 61.55, 61.35, 60.15, 59.80, 59.30, 57.23,
56.61, 56.25, 56.01, 55.24, 54.26, 54.15, 54.05, 53.64, 51.55,
51.13, 50.98, 50.86, 48.80, 43.21, 37.35, 37.06, 36.65, 31.68,
31.16, 30.87, 30.03, 27.42, 26.87, 25.48, 25.32, 22.44, 19.39,
19.12, 18.37, 15.47, 15.43, 11.26, 10.45. HRMS (TOF-MS-ES) m/z
2633.0002 [M+H], 1315.9836 [Mꢀ2H], 876.6529 [Mꢀ3H],
(2633.0006 Calcd for C109H158N25O45S3 [M+H]).
tion of gp120 and antibodies, and the NIH AIDS Research and Ref-
erence Regent Program for soluble CD4. This work was supported
by the NIDDK (C.A.B.) and NIAID (P.D.K. and R.W.) Intramural Re-
search Programs, a grant from the Bill and Melinda Gates Founda-
tion Grand Challenges in Global Health Initiative (P.D.K. and R.W.),
and the Intramural AIDS Targeted Antiviral Program (IATAP) of the
Office of the Director, NIH (C.A.B.).
Supplementary data
Spectral data for protected amino acids 10 and 11, peptides 12
and 13, and complete 1H and 13C assignments for peptides 2–4, 6, 7
and 14. Supplementary data associated with this article can be
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Azide 12 (10 mg, 3.8 lmol) was dissolved in MeOH/H2O/HOAc
10. An alternate explanation may in part be attributed to the absence of
a
(1:4:0.1, 5 mL) and Pd/C (5 mg) was added. The flask was evacu-
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To a solution of azide 12 (14.7 mg, 5.6
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lmol) in PBS/tert- butyl
l
lL), sodium
l
l
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Acknowledgments
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We thank J. Lloyd for HRMS data, J. Robinson for 412d and 2.2c
antibodies, C.-C. Huang for assistance with expression and purifica-