72
S. Tsujita et al. / Bioorg. Med. Chem. Lett. 17 (2007) 68–72
8. Recent reviews and example Ramstrom, O.; Bun-
Acknowledgments
yapaiboonsri, T.; Lohmann, S.; Lehn, J. M. Biochim.
Biophys. Acta 2002, 1572, 178; Rowan, S. J.; Cantrill, S. J.;
Cousins, G. R.; Sanders, J. K.; Stoddart, J. F. Angew.
Chem., Int. Ed. 2002, 41, 898; Ladame, S.; Whitney, A. M.;
Balasubramanian, S. Angew. Chem., Int. Ed. 2005, 44, 5736.
9. Synthesis. 2S: (i) 1, (ClH3NCH2CH2S)2, HOBT, DCC,
DMSO, rt; (ii) DTT, H2O; 2M: (i) 1, BocNHCH2–
(CH2OCH2)2CH2SBz, HOBT, DCC, DMF, 100 ꢁC; (ii)
0.2 M NaOH; 2L: (i) three times repetition of the following
two procedures with 2-chlorotritylcysteamine resin; (a)
FmocNHCH2(CH2OCH2)2COOH, HBT, HBTU, DIPEA,
DMF, NMP; (b) 20% piperidine, DMF; (ii) 1: BOP, HBT,
DIPEA, DMF, NMP; (iii) 10% TFA, CH2Cl2; 3: 2, CH3I,
Et3N, CH3OH, 4: 2, GSSG, GSH, 5M: (i) 1,
H2NCH2CH2OCH2CH2NHBoc, BOP, HBT, DIPEA,
DMF; (ii) TFA, CH2Cl2; (iii) acrylic acid N-hydroxysucci-
mide ester; (iv) GSH, pH 8, 5L: (i) two times repetition of
the following two procedures with O-bis(aminoethyl)ethyl-
ene-glycotrityl resin; (a) FmocNHCH2–(CH2OCH2)2–
COOH, HBT, HBTU, DIPEA, DMF, NMP; (b) 20%
piperidine, DMF; (ii) 1, BOP, HBT, DIPEA, DMF, NMP;
(iii) 10% TFA, CH2Cl2; (iv) acrylic acid N-hydroxysucci-
mide ester; (v) GSH, pH 8. Spectral Data: 2S-SS-2S: IR
This work has been supported by a Grant-in Aid for Sci-
entific Research (A) from Japan Society for the Promo-
tion of Science (JSPS), and CREST from Japan Science
and Technology Agency (JST).
References and notes
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1
(cmꢀ1) 1670, MS (ESI) m/e 527.21 (M+2H+)/2, H NMR
(CD3OD–NaOH) d (ppm), J (Hz), 7.97 (2H, s), 7.78 (4H, d,
J = 8.85), 7.69 (2H, d, J = 8.54), 7.45 (2H, d, J = 2.14), 7.31
(2H, d, J = 8.24), 6.90 (4H, d, J = 8.56), 6.83 (2H, d,
J = 2.14), 4.04 (4H, t, J = 6.95), 3.31–3.25 (12H, m), 3.21
(8H, s, br), 2.86 (6H, s). 2M: IR (cmꢀ1) 1675, MS (ESI) m/e
`
Dixon, I. M.; Lopez, F.; Esteve, J. P.; Tejera, A. M.;
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1
616.21 (M+H+), H NMR (CD3OD) d (ppm), J (Hz), 8.48
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(1H, s), 8.35 (1H, d, J = 8.54), 8.03 (2H, d, J = 8.85), 7.87
(1H, d, J = 8.54), 7.73 (2H, d, J = 2.13), 7.35 (1H, d,
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3.54–3.48 (8H, m), 3.38–3.35 (8H, m), 3.33–3.29 (2H, m),
3.21 (2H, t, J = 5.04), 3.01 (3H, s), 2.57 (2H, t, J = 7.02).
´
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