P. Ruzza et al. / Tetrahedron Letters 43 (2002) 3769–3771
3771
getto Strategico ‘Controlli post-trascrizionali dell’e-
spressione genica’ and Progetto Strategico ‘Biotecnolo-
gie’).
sizer User’s Manual, Applied Biosystems Inc., Foster
City, CA, 1989.
12. ESI-MS m/z=1095 [MH]+; tr (min) 25.6 min. (Elution
conditions: eluent A, 0.05% TFA in water; eluent B,
0.05% TFA in 9:1 v/v acetonitrile–water; column Jupiter
C18, 10 m, 250×4.6 mm; flow rate 1 ml/min; detection at
216 and 275 nm; isocratic elution at 5% B for 3 min and
then linear gradient from 5 to 30% B in 40 min). Amino
acid ratios in acidic hydrolyzate: Asp 1.92 (2), Glu 4.07
(4), Val 0.98 (1), Hba-Gly 0.95 (1).
References
1. Hruby, V. J.; Li, G.; Haskett-Luevano, C.; Shenderovich,
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13. Characteristic data for the key compounds. Compound 2:
1H NMR (DMSO-d6): l (ppm) 7.81–7.55 (m, arom. Pht);
7.35 (m, arom. Bzl); 7.2–6.95 (d, arom. Tyr); 5.06 (s, CH2
Bzl); 4.65 (m, CaH); 3.85 (CaH Gly); 3.18–2.8 (dd, CbH).
Compound 3: 1H NMR (DMSO-d6): l (ppm) 7.83 (m,
arom. Pht); 7.35 (m, arom. Bzl); 7.06–6.81 (d, arom. Tyr);
5.55–5.30 (d, CH2); 5.15 (m, CaH Tyr); 4.98 (m, CH2
Bzl); 4.15–4.08 (dd, CaH2 Gly); 3.3 (m, CbH2). Com-
pound 4: 1H NMR (DMSO-d6): l (ppm) 9.40 (s, OH);
7.90 (m, arom. Pht); 7.04 (d, arom.); 6.72 (s, arom.); 6.68
(d, arom.); 5.20 (m, CaH Tyr); 4.81–4.48 (dd, CoH);
4.22–4.03 (dd, CaH Gly); 3.16–3.12 (dd, CbH). Com-
pound 5: 1H NMR (DMSO-d6): l (ppm) 9.75 (s, OH);
7.52 (d, arom.); 7.38 (d, arom.); 6.62 (s, arom.); 5.07, 4.04
(d, CoH); 4.81 (m, CaH Hba); 4.27, 3.98 (d, CaH Gly);
2.69, 2.83 (dd, CbH). Compound 6: 1H NMR (DMSO-
d6): l (ppm) 9.3 (s, OH); 7.45 (m, NH); 7.25–7.9 (m,
arom. Fmoc); 6.92 (d, arom.); 6.64 (m, arom.); 6.58 (s,
arom.); 5.08 (m, CaH Tyr); 5.10–4.02 (d, CoH); 4.32 (m,
CH2 Fmoc); 4.25 (m, CH Fmoc); 4.20–3.90 (CaH Gly);
3.06–2.86 (m, CbH); ESIMS m/z=473.2 [MH]+.
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11. Applied Biosystems, Inc., Model 431A Peptide Synthe-