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Syntheses and Conformational Studies of Polyacidic Amino Acids Containing Optical Active Side Chains

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Molecular Evolution

Abstract

The syntheses and physicochemical properties of poly ( β-alkyl aspartate) and poly( γ-alkyl glutamate) have been widely investigated (1–11). Optical rotatory dispersion (ORD) and circular dichroism (CD) have led to the conclusion that many L-polypeptides have a right-handed helical sense. Poly( γ-alkyl L-glutamate) assumes a right-handed helical conformation in a solvent such as chloroform, while it assumes a disordered conformation in a solvent such as dichloroacetic acid (DCA) or trifluoroacetic acid (TFA). Polymers of β-methyl and β-benzyl L-aspartates represent exceptions to the general rule and exist as left-handed helices in chloroform and in methylene dichloride solutions. The introduction of a nitro, methyl, chloro, or cyano group into the para position of the aromatic ring in the side chain of poly( β-benzyl L-aspartate) causes a reversal of the left-handed helix of the poly- α-amino acid in chloroform (12, 13). In addition, poly( β-benzyl L-aspartate) is known to undergo a polymorphic transition from the α-helix to the ω-helix when a solid film is heated in vacuo (14).

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© 1972 Plenum Press

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Hayakawa, T., Yamamoto, H. (1972). Syntheses and Conformational Studies of Polyacidic Amino Acids Containing Optical Active Side Chains. In: Rohlfing, D.L., Oparin, A.I. (eds) Molecular Evolution. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-2019-7_20

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  • DOI: https://doi.org/10.1007/978-1-4684-2019-7_20

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4684-2021-0

  • Online ISBN: 978-1-4684-2019-7

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