Controlling the Helicity of Hydroxyquinoline Metal Complexes
C(CH3)3] ppm. 13C NMR (125 MHz, CDCl3): δ = 152.1 (q, C=O),
151.3 (t, Car), 147.6 (q, Car), 140.8 (q, Car), 135.6 (t, Car), 131.6 (q,
Car), 128.9 (q, Car), 127.1 (t, Car), 125.8 (t, Car), 121.7 (t, Car), 84.0
[q, C(CH3)3], 29.8 (s, CH2-Br), 27.9 [p, C(CH3)3] ppm. IR (KBr):
(log ε) = 246 (4.84), 335 (3.85) nm. HRMS (ESI): calcd. for
C57H60N12O6 [M + H]+ 1009.4832; found 1009.4782. HRMS (ESI):
calcd. for C57H60N12O6 [M + Na]+ 1031.4651; found 1031.4616.
ν = 3438, 3062, 3036, 2987, 2978, 2932, 1758, 1281, 1241,
˜
1149 cm–1. UV/Vis (DCM, c = 2.97ϫ10–4 mmolmL–1): λ (log ε) =
306 (3.90) nm. HRMS (ESI): calcd. for C15H16BrNO3 [M(81Br) +
H]+ 340.0367; found 340.0362. HRMS (ESI): calcd. for
C15H16BrNO3 [M(79Br) + H]+ 338.0386; found 338.0381. HRMS
(ESI): calcd. for C15H16BrNO3 [M(81Br) + Na]+ 362.0187; found
362.0182. HRMS (ESI): calcd. for C15H16BrNO3 [M(79Br) + Na]+
360.0206; found 360.0202. C15H16BrNO3 (338.20): calcd. C 53.27,
H 4.77, N 4.14, Br 23.63; found C 53.48, H 5.07, N 4.01, Br 23.41.
Acknowledgments
This work was generously supported by the Deutsche Forschungs-
gemeinschaft. The authors thank Dr. Andreea Schuster for helpful
discussions.
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Cyclopeptide 9: To quinoline 7 (46 µmol, 25 mg) in acetonitrile
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100 mg) and scaffold 1 (296 µmol, 100 mg). The solution was
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4
NMR (500 MHz, CDCl3): δ = 8.81 (d, JH,H = 2.3 Hz, 1 H, Har),
8.45 (d, 3JH,H = 9.4 Hz, 1 H, NH), 7.67 (s, 1 H, Har), 7.53–7.55 (m,
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˜
3 2
3
3066, 2932, 1757, 1655, 1496, 1273, 1234, 1143 cm–1. UV/Vis
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1
4
99%). H NMR (500 MHz, MeOD): δ = 8.84 (d, JH,H = 1.8 Hz,
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[d, JH,H = 6.7 Hz, 3 H, CH(CH3)2] ppm. 13C NMR (125 MHz,
MeOD): δ = 164.6 (q, C=O), 151.8 (q, Cimi), 149.4 (q, Ciso), 145.4
(t, Ciso), 140.0 (t, Ciso), 134.3 (q, Ciso), 132.1 (q, Cimi), 131.1 (q,
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