Predictable Conformational Diversity in Foldamers of Sugar Amino Acids

Dóra K. Menyhárd, Ilona Hudáky, Imre Jákli, György Juhász, A. Perczel

Research output: Contribution to journalArticle

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Abstract

A systematic conformational search was carried out for monomers and homohexamers of furanoid β-amino acids: cis-(S,R) and trans-(S,S) stereoisomers of aminocyclopentane carboxylic acid (ACPC), two different aminofuranuronic acids (AFUα and AFUβ), their isopropylidene derivatives (AFU(ip)), and the key intermediate β-aminotetrahydrofurancarboxylic acid (ATFC). The stereochemistry of the building blocks was chosen to match that of the natural sugar amino acid (xylose and ribose) precursors (XylAFU and RibAFU). The results show that hexamers of cis-furanoid β-amino acids show great variability: while hydrophobic cyclopentane (cis-ACPC)6 and hydrophilic (XylAFUα/β)6 foldamers favor two different zigzagged conformation as hexamers, the backbone fold turns into a helix in the case of (cis-ATFC)6 (10-helix) and (XylAFU(ip))6 (14-helix). Trans stereochemistry resulted in hexamers exclusively with the right-handed helix conformation, (H12 P)6, regardless of their polarity. We found that the preferred oligomeric structure of XylAFUα/β is conformationally compatible with β-pleated sheets, while that of the trans/(S,S) units matches with α-helices of proteins.

Original languageEnglish
Pages (from-to)757-768
Number of pages12
JournalJournal of Chemical Information and Modeling
Volume57
Issue number4
DOIs
Publication statusPublished - Apr 24 2017

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Sugars
Amino acids
Stereochemistry
NSC 153174
Carboxylic Acids
Carboxylic acids
Amino Acids
Acids
Conformations
Cyclopentanes
Stereoisomerism
Xylose
Ribose
Monomers
Derivatives
Proteins
propylene

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)
  • Computer Science Applications
  • Library and Information Sciences

Cite this

Predictable Conformational Diversity in Foldamers of Sugar Amino Acids. / Menyhárd, Dóra K.; Hudáky, Ilona; Jákli, Imre; Juhász, György; Perczel, A.

In: Journal of Chemical Information and Modeling, Vol. 57, No. 4, 24.04.2017, p. 757-768.

Research output: Contribution to journalArticle

Menyhárd, Dóra K. ; Hudáky, Ilona ; Jákli, Imre ; Juhász, György ; Perczel, A. / Predictable Conformational Diversity in Foldamers of Sugar Amino Acids. In: Journal of Chemical Information and Modeling. 2017 ; Vol. 57, No. 4. pp. 757-768.
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