Side chain-specific 11/9-helix propensity of α/β-peptides with alternating residue types

Jaeyeon Lee, Jihyun Shim, Philjae Kang, Moon Gun Choi, Soo Hyuk Choi

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

The 11/9-helix is among the most stable and non-traditional helical structures for α/β-peptides with alternating residue types. The effect of side chain groups of α-residues and β 3 -residues on the 11/9-helix propensity was examined under various solvent conditions. An α-amino acid residue with one of the four representative side chain groups was incorporated into the central position of an α/β-pentapeptide backbone. A β-branched valine residue did not show any destabilizing effect. α,α-Dimethylsubstituted Aib residue was tolerated under nonpolar conditions, but did not promote 11/9-helical folding. The oligomer with a glycine residue did not show 11/9-helical folding under polar solvent conditions. The single unmatched stereochemistry of d-alanine was deleterious to 11/9-helical folding. Replacement of a cyclic β-residue with an acyclic β 3 -residue in the 11/9-helical structure had a slight destabilizing effect, which could be compensated by a longer peptide sequence with more cyclic β-residues. These results provide a guidance for incorporating functional groups into an 11/9-helical α/β-peptide backbone to design functional oligomers.

Original languageEnglish
Pages (from-to)433-438
Number of pages6
JournalOrganic and Biomolecular Chemistry
Volume16
Issue number3
DOIs
Publication statusPublished - 2018 Jan 1

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helices
peptides
Oligomers
Peptides
Stereochemistry
Valine
Alanine
Glycine
Functional groups
folding
Amino Acids
oligomers
stereochemistry
alanine
glycine
amino acids

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Lee, Jaeyeon ; Shim, Jihyun ; Kang, Philjae ; Choi, Moon Gun ; Choi, Soo Hyuk. / Side chain-specific 11/9-helix propensity of α/β-peptides with alternating residue types. In: Organic and Biomolecular Chemistry. 2018 ; Vol. 16, No. 3. pp. 433-438.
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Side chain-specific 11/9-helix propensity of α/β-peptides with alternating residue types. / Lee, Jaeyeon; Shim, Jihyun; Kang, Philjae; Choi, Moon Gun; Choi, Soo Hyuk.

In: Organic and Biomolecular Chemistry, Vol. 16, No. 3, 01.01.2018, p. 433-438.

Research output: Contribution to journalArticle

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