Effect of acetylation and permethylation on the conformation and candidacidal activity of salivary histatin-5

Kalaiyarasi Ramalingam, Narayanan Ramasubbu, Michael J. Levine

Research output: Contribution to journalArticlepeer-review


Salivary histatins provide the non-immune defense against oral pathogens such as Candida albicans. The structural requirements of histatin-5 for anticandida activity were examined with respect to its ability to adopt helical structures, its electrostatic interactions and the hydrogen-bonding potency of its basic residues. For this purpose, the lysine and/or histidine residues of histatin-5 were chemically modified by acetylation and permethylation. Acetylated histatin-5 retained its ability to adopt helical structures in 2,2,2-trifluoroethanol, but completely lost its ability to kill yeast cells. In contrast, permethylated histatin-5 shows very little tendency to adopt a helical structure, but retained significant anticandida activity. The results suggest that the candidacidal activity can arise even when the histatin does not have the ability to adopt helical structures. The candidacidal activity of the derivatives is discussed in terms of electrostatic interactions and hydrogen-bonding potency.

Original languageEnglish (US)
Pages (from-to)349-356
Number of pages8
JournalInternational Journal of Peptide Research and Therapeutics
Issue number6
StatePublished - 1996
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Bioengineering
  • Biochemistry
  • Molecular Medicine
  • Drug Discovery


  • Candida albicans
  • Histatins
  • Peptide synthesis
  • Permethylation
  • Structure


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