N'-alkylated guanidiniocarbonyl pyrroles: new receptors for amino acid recognition in water.
[reaction: see text] N'-Substituted guanidiniocarbonyl pyrroles 7 were synthesized for the first time by activation of a Boc-protected guanidiniocarbonyl pyrrole 3 with triflic anhydride and subsequent reaction with a primary amine. These guanidinium cations are efficient receptors for the complexation of amino acid carboxylates even in water (K(assoc) > 10(3) M(-1)) as could be shown by UV titration studies.
Schmuck
Carsten
C
Institute of Organic Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany. schmuck@chemie.uni-wuerzburg.de
Bickert
Volker
V
D000478:Alkylation; D000596:Amino Acids / Q000737:chemistry* / Q000378:metabolism; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry*; D012996:Solutions; D013057:Spectrum Analysis; D017186:Titrimetry; D014633:Valine / Q000737:chemistry / Q000378:metabolism; D014867:Water / Q000737:chemistry
D000596:Amino Acids; D011758:Pyrroles; D012996:Solutions; D014867:Water; D014633:Valine