N-Maleoyl Amino Acid Succinimido Esters
307
Data
1a: 1H NMR (CDCl3, d, ppm) 2.81 (4H, s, 2 ꢀ CH2), 3.01 (2H, t, J ¼ 6.9 Hz,
CH2CO2), 3.93 (2H, t, J ¼ 6.9 Hz, CH2N), 6.73 (2H, s, 2 ꢀ 55CH). 13C NMR
(CDCl3, d, ppm) 25.93, 30.12, 33.38, 134.69, 167.37, 169.09, 170.46.
1b: 1H NMR (CDCl3, d, ppm) 1.00–2.61 (10H, m, cyclohexyl CH2, CH), 2.81
(4H, s, 2 ꢀ CH2), 3.38 (2H, d, J ¼ 6.9 Hz, NCH2), 6.70 (2H, s, 2 ꢀ 55CH).
13C NMR (CDCl3, d, ppm) 25.98, 28.40, 29.70, 36.47, 40.80, 43.79, 134.32,
169.54, 170.99, 171.37.
1c: 1H NMR (CDCl3, d, ppm) 2.91 (4H, s, 2 ꢀ CH2), 6.90 (2H, s, 2 ꢀ 55CH),
7.63 (2H, d, J ¼ 8.7 Hz, Ar), 8.23 (2H, d, J ¼ 8.7 Hz, Ar). 13C NMR (CDCl3,
d, ppm) 26.08, 124.16, 125.61, 131.87, 134.90, 137.70, 161.55, 169.05,
169.53.
1d: 1H NMR (CDCl3, d, ppm) 2.91 (4H, s, 2 ꢀ CH2), 6.89 (2H, s, 2 ꢀ 55CH),
7.60–7.82 (2H, m, Ar), 8.12–8.18 (2H, m, Ar). 13C NMR (CDCl3, d, ppm)
26.07, 126.69, 128.10, 130.04, 130.17, 132.41, 134.80, 161.49, 169.25, 169.44.
1e: 1H NMR (CDCl3, d, ppm) 2.89 (4H, s, 2 ꢀ CH2), 3.90 (3H, s, OCH3), 6.87
(2H, s, 2 ꢀ 55CH), 7.10 (1H, d, J ¼ 8.9 Hz, Ar), 7.90 (1H, d, J ¼ 2.2 Hz, Ar),
8.22 (1H, dd, J ¼ 8.8, 2.2, Ar). 13C NMR (CDCl3, d, ppm) 26.06, 56.82,
112.43, 118.06, 120.79, 133.34, 134.31, 135.03, 161.05, 169.38, 169.59.
REFERENCES
1. Kirkley, J.E.; Goldstein, A.L.; Naylor, P.H. Effect of peptide-carrier coupling on
peptide-specific immune responses. Immunobiol. 2001, 203, 601–615.
2. Yukawa, N.; Osawa, M.; Saito, T.; Hasegawa, T.; Matsuda, H.; Takahama, K.;
Takeichi, S. Bispecific rabbit Fab0-bovine serum albumin conjugate used in
hemagglutination immunoassay for b-microseminoprotein. J. Immunoassay
1997, 18, 215–233.
3. Gruber, H. J.; Kada, G.; Pragl, B.; Riener, C.; Hahn, C. D.; Harms, G. S.;
Ahrer, W.; Dax, T. G.; Hohenthanner, K.; Knaus, H. G. Preparation of thiol-
reactive Cy5 derivatives from commercial Cy5 succinimidyl ester. Bioconjugate
Chem. 2000, 11, 161–166.
4. Pozsgay, V.; Vieira, N. E.; Yergey, A. A method for bioconjugation of carbo-
hydrates using Diels-Alder cycloaddition. Org. Lett. 2002, 4, 3191–3194.
5. Wang, L. X.; Ni, J. H.; Singh, S. Carbohydrate-centered maleimide clusters as a
new type of templates for multivalent peptide assembling: Synthesis of multivalent
HIV-1 gp41 peptides. Bioorg. Med. Chem. 2003, 11, 159–166.
6. Meyer-Losic, F.; Quinonero, J.; Dubois, V.; Alluis, B.; Dechambre, M.;
Michel, M.; Cailler, F.; Fernandez, A.-M.; Trouet, A.; Kearsey, J. Improved thera-
peutic efficacy of doxorubicin through conjugation with a novel peptide drug
delivery technology (Vectocell). J. Med. Chem. 2006, 49, 6908–6916.