Abstract
Amino acid N-carboxy anhydrides (amino acid NCAs) can be polymerized using a butylamine initiator in dioxane or N,N-dimethylformamide solution or in heterogeneous acetonitrile systems in which the NCAs dissolve but the resulting polymers do not. NCAs can also be polymerized in the solid state, using the same initiator. The solid-state polymerization was carried out by dipping amino acid NCA crystals in hexane (an inactive solvent) and adding butylamine to the mixture. Each polymerization was carried out under strict conditions, preventing moisture contamination. Solid-state polymerization has the following features typical of topochemical polymerization. (1) Many amino acid NCAs are more reactive in the solid state than in solution or heterogeneous systems. (2) Many amino acid NCAs give polypeptides with molecular weights higher than those obtained in solution or heterogeneous systems. (3) Many amino acid NCAs give poly(amino acid)s with molecular conformations that are different from those obtained in solution or heterogeneous systems. The reaction is not topotactic, because the resulting polypeptides are not crystals. The solid-state polymerization of amino acid NCAs is useful for the preparation of any type of polypeptide, unlike solution reactions.
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Kanazawa, H. (2015). Topochemical Polymerization of Amino Acid N-Carboxy Anhydrides in Crystalline State. In: Tamura, R., Miyata, M. (eds) Advances in Organic Crystal Chemistry. Springer, Tokyo. https://doi.org/10.1007/978-4-431-55555-1_25
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DOI: https://doi.org/10.1007/978-4-431-55555-1_25
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