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Molecular recognition of hydrophobic ammonium substrates by a cationic octopus cyclophane bearing noncovalently bound pyridoxal-5′-phosphate: A vitamin B6-dependent holoenzyme model

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Abstract

The inclusion behavior of the octopus cyclophane constructed with a rigid macrocyclic skeleton and eight hydrocarbon chains was studied in aqueous media by means of fluorescence and electronic absorption spectroscopy. Both hydrophobic and electrostatic interactions came into effect in the host-guest complexation process. The cyclophane acted as an effective apoenzyme model for constitution of an artificial vitamin B6-dependent holoenzyme by simultaneous incorporation of pyridoxal-5′-phosphate and a hydrophobic alkylammonium substrate into the host cavity to give the Schiff-base species, showing the substrate selectivity.

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Correspondence to Yukito Murakami.

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Murakami, Y., Kikuchi, J. & Hayashida, O. Molecular recognition of hydrophobic ammonium substrates by a cationic octopus cyclophane bearing noncovalently bound pyridoxal-5′-phosphate: A vitamin B6-dependent holoenzyme model. J Incl Phenom Macrocycl Chem 7, 91–97 (1989). https://doi.org/10.1007/BF01112786

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Key words

  • Cyclophane
  • pyridoxal-5′-phosphate
  • Schiff base
  • vitamin B6
  • hydrophobic interaction
  • enzyme model