Incorporation of diacids into the polyglycine II structure: Model studies

Abstract

Aliphatic diacids Eare often incorporated into polypeptide structures in order to obtain model compounds for hormones, protein turns, etc. They are also fundamental components of many commercial polyamides. On the other hand glycine, the simplest amino acid, shows unique conformational features. In order to better understand the structure of such compounds, we have synthetized and determined the molecular structure of three models represented by the general formula CH₃‐CH₂CH₂‐NH‐CO‐CH₂NH‐CO‐(CH₂)_n‐2‐CO‐NH‐CH₂CO‐NH‐CH₂CH₂CH₃, with n = 3, 4, or 6. Conformational differences have been found in the dicarboxylic moiety, whereas glycine always has the polyglycine II conformation. The ‐CO‐(CH₂)_n‐2‐CO‐ segment adopts a folded conjformation: SS, TGT, and SḠTGS̄ for n = 3, 4, and 6, respectively. Molecular packing is always pseiidohexagonal and a network of hydrogen bonds oriented in three directions at 120° is formed. The results are of interest in order to provide information about polyamides in which gljrine residues are incorporated. Our results confirm the tendency of glycine residues to adopt the polyglycine II conformation in its copolymers with aliphatic compounds. © 1995 John Wiley & Sons, Inc.