Synthesis of a 2-arylsulphonylated tryptophan: the antibacterial activity of bovine lactoferricin peptides containing Trp(2-Pmc).
A modified tryptophan, beta-[2-(2,2,5,7,8-pentamethylchroman-6-sulphonyl)-indol-3-yl]alanine, Trp(2-Pmc) = Tpc has been synthesized. Replacement of tryptophan in a bovine lactoferricin model peptide with the modified tryptophan resulted in peptides with a substantially increased antibacterial activity against Escherichia coli and Staphylococcus aureus. The most active peptides against each bacterial strain displayed minimal inhibitory concentrations of 7.5 microg/ml.
Haug
Bengt Erik
BE
Department of Chemistry, University of Tromsø, Norway.
Andersen
Jill
J
Rekdal
Oystein
O
Svendsen
John S
JS
D000409:Alanine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000494:pharmacology*; D002417:Cattle; D004926:Escherichia coli / Q000187:drug effects; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007781:Lactoferrin / Q000031:analogs & derivatives / Q000737:chemistry* / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D010455:Peptides; D013211:Staphylococcus aureus / Q000187:drug effects; D014364:Tryptophan / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism*
C470611:(2-(2,2,5,7,8-pentamethylchroman-6-sulphonyl)-indol-3-yl)alanine; D000900:Anti-Bacterial Agents; D007211:Indoles; D010455:Peptides; D014364:Tryptophan; D007781:Lactoferrin; D000409:Alanine