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Synthesis and conformational study of poly(Nϵ-benzyl-L-lysine) and its benzyloxycarbonyl derivative

✍ Scribed by Hiroyuki Yamamoto; Tadao Hayakawa

Publisher
Wiley (John Wiley & Sons)
Year
1972
Tongue
English
Weight
511 KB
Volume
11
Category
Article
ISSN
0006-3525

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✦ Synopsis

The solvent-and pH-induced conformational changes are examined in order to investigate the influence of benzy 1 group. Polymer was prepared via N'-benzyloxycarbonyl, N'-benzyl-Nu-carboxy-clysine anhydride. The resulting poly(iV'-benzyloxycarbonyl, N'-benzyl-clysine) was obtained in a high yield and had a high molecular weight. The protected polymer was removed into poly(N'-benzyl-L-lysine) by treating it with hydrogen bromide. From the results of the ORD and CD, the protected polymer has a righthanded a-helix, showing [m']233 = -10,300, [ e l 2 2 0 = -27,600, and [0]207 = -25,100 in dioxane. The breakdown of the helical conformation is found to occur a t 8% dichloroacetic acid in a chloroform-dichloroacetic acid mixture. In the pH range 3.35-6.90, poly(Nc-benzyl-blysine) is in a random coil structure. In the pH range 7.50-13.0, the polypeptide has a right-handed a-helix structure; [m']233 = -12,000, [ e l 2 2 0 = -27,200, and [0]2,,7 = -27,000. In comparison with poly-L-lysine, the coil-to-helix transition is observed a t lower pH range in SOYo n-propanol. Above pH 8 by heating, the a -.. p transition of poly(Nf-benzyl-L-lysine) is not observed in an aqueous media.

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