Molecular recognition of aqueous dipeptides at multiple hydrogen-bonding sites of mixed peptide monolayers

Xiao Cha, Katsuhiko Ariga, Toyoki Kunitake

Research output: Contribution to journalArticle

114 Citations (Scopus)

Abstract

Oligopeptide amphiphiles with different dipeptide moieties of -XYNH2 (X = Gly and Ala, Y = GLy, Ala, Val, Leu, and Phe) were synthesized. Binding of aqueous dipeptides onto monolayers of equimolar mixtures of these amphiphiles with a benzoic acid amphiphile (2C18BCOOH) was investigated by π-A isotherm measurement, FT-IR spectroscopy, and XPS elemental analysis. For given GIyX dipeptides (X = neutral and hydrophobic residues), the binding ratio was lessened with increasing sizes of the side chain of the Y residue in the GlyY dipeptide moiety of the host amphiphiles. The Langmuir-type saturation behavior was observed for binding of GlyLeu to an equimolar monolayer of 2C18BGly2NH2 and 2C18BCOOH. Its binding constant of 475 M-1 was 10 times larger than that observed for a single-component monolayer of 2C18BGly2NH2 (K = 35 M-1). The saturation guest/host ratio was 0.47. The mode of substrate insertion into the binding site was examined by FT-IR spectroscopy. When the hydrophobic residue was on the C-terminal of a guest dipeptide (GlyX), the C-terminal insertion was selected with accompanying formation of cyclic carboxylic acid dimers at the interface. In the case of XGly guests, the N-terminal insertion with salt bridge formation with the host was observed. When the two residues of a dipeptide had close hydrophobicities, both C- and N-terminal insertions were observed. Formation of these binding sites is apparently induced by dipeptide binding.

Original languageEnglish
Pages (from-to)9545-9551
Number of pages7
JournalJournal of the American Chemical Society
Volume118
Issue number40
DOIs
Publication statusPublished - Oct 9 1996

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Molecular recognition
Dipeptides
Hydrogen Bonding
Peptides
Monolayers
Hydrogen bonds
Amphiphiles
Binding sites
Infrared spectroscopy
Spectrum Analysis
Binding Sites
Oligopeptides
Benzoic Acid
Benzoic acid
Hydrophobicity
Carboxylic Acids
Hydrophobic and Hydrophilic Interactions
Carboxylic acids
Dimers
Isotherms

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Molecular recognition of aqueous dipeptides at multiple hydrogen-bonding sites of mixed peptide monolayers. / Cha, Xiao; Ariga, Katsuhiko; Kunitake, Toyoki.

In: Journal of the American Chemical Society, Vol. 118, No. 40, 09.10.1996, p. 9545-9551.

Research output: Contribution to journalArticle

Cha, Xiao ; Ariga, Katsuhiko ; Kunitake, Toyoki. / Molecular recognition of aqueous dipeptides at multiple hydrogen-bonding sites of mixed peptide monolayers. In: Journal of the American Chemical Society. 1996 ; Vol. 118, No. 40. pp. 9545-9551.
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