An extended planar C5 conformation and a 310-helical structure of peptide foldamer composed of diverse α-ethylated α,α-disubstituted α-amino acids

Masakazu Tanaka, Shin Nishimura, Makoto Oba, Yosuke Demizu, Masaaki Kurihara, Hiroshi Suemune

Research output: Contribution to journalArticle

36 Citations (Scopus)

Abstract

Optically active peptide foldamers Tfa-[(S)-(αEt)Leu]-[(S)-(αEt)Nva]-Deg-[(S)-(αEt)Nle]-OEt (10) and Tfa-[(S)-(αEt)Val]-[(S)-(αEt)Leu]- [(S)-(αEt)-Nva]-Deg-[(S)-(αEt)Nle]-OEt (11) composed of diverse α-ethylated α,α-disubstituted α-amino acids were synthesized. The dominant conformation of these peptides in solution was an unusual, fully extended planar conformation, and that in the crystal state was both right-handed (P) and left-handed (M) 310-helical structures in 10 and a P 310-helical structure in 11, respectively. The preferred planar C5 conformation of the peptides prepared from chiral α-ethylated α,α-disubstituted α-amino acids was drastically different from the 310-helical structure of the peptides prepared from chiral α-methylated α,α-disubstituted α-amino acids.

Original languageEnglish
Pages (from-to)3082-3090
Number of pages9
JournalChemistry - A European Journal
Volume9
Issue number13
DOIs
Publication statusPublished - Jul 7 2003

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Peptides
Conformations
Amino acids
Amino Acids
Crystals
C5-peptide

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

Cite this

An extended planar C5 conformation and a 310-helical structure of peptide foldamer composed of diverse α-ethylated α,α-disubstituted α-amino acids. / Tanaka, Masakazu; Nishimura, Shin; Oba, Makoto; Demizu, Yosuke; Kurihara, Masaaki; Suemune, Hiroshi.

In: Chemistry - A European Journal, Vol. 9, No. 13, 07.07.2003, p. 3082-3090.

Research output: Contribution to journalArticle

Tanaka, Masakazu ; Nishimura, Shin ; Oba, Makoto ; Demizu, Yosuke ; Kurihara, Masaaki ; Suemune, Hiroshi. / An extended planar C5 conformation and a 310-helical structure of peptide foldamer composed of diverse α-ethylated α,α-disubstituted α-amino acids. In: Chemistry - A European Journal. 2003 ; Vol. 9, No. 13. pp. 3082-3090.
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