Peptide Analogues of DNA Consisting of l-α-Amino-γ-thymine Butyric Acid and l-Valine Subunits

References

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• The product crystallized from ethanol or ethyl acetate. UV (MeOH) : λmax = 254 nm (ε = 184000) 1H NMR (CDCl3) : δ 1.4 (9H,s,3xCH3 Boc), 1.9 (3H,s,CH3 thym.), 2.2(2H,m,bCH2), 3.8 (2H,m,gCH2), 4.4 (1H,br s,CH), 5.2 (2H,s,Bn), 5.3 (1H,d,NH), 7.1 (1H,s,6-H), 7.3–7.7 (8H,m,ar.), 7.9 (2H,d,o-Bz) ppm. 13C NMR (CDCl3) : δ 171.4 (COO), 163.0 (C-4), 155.0 (ureth.), 149.8 (C-2), 140.3 (C-6), 134.9 (Ci), 131.5–128.4 (ar.), 110.8 (C-5), 80.4 (C Boc), 67.9 (Bn), 51.2 (CH), 45.6 (gCH2), 31.4 (bCH2), 28.2 (3xCH3 Boc), 12.3 (CH3 thym.) ppm.
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• UV (MeOH) : λmax = 272 nm (ε = 7900) 1H NMR (CD3OD) : δ 1.4 (9H,s,3xCH3 Boc), 1.9 (3H,s,CH3 thym.), 2.2 (2H,m,βCH2), 3.8 (2H,m, γCH2), 4.1 (1H,br s,CH), 7.4 (1H,s,6-H) ppm. 13C NMR (CD3OD) : δ 174.3 (COO), 165.9 (C-4), 157.1 (ureth.), 152.0 (C-2), 142.3 (C-6), 110.2 (C-5), 79.8 (C Boc), 51.5 (CH), 45.6 (γCH2), 30.5 (βCH2), 27.8 (3xCH3 Boc), 11.3 (CH3 thym.) ppm. MS (+FAB) : 328 [M+H]+
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• Analyses were done using an acid buffer containing cyclodextrin as the chiral selector ,
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