Reduction of a 4-pyrrole phenylacyl-containing peptide with trifluoroacetic acid-triisopropylsilane-phenol-H2O during solid-phase peptide synthesis and its protein kinase C alpha inhibitory activity.
Cleavage of 4-pyrrole phenylacyl TentaGel-appended peptide (5) containing Arg(Pbf) with trifluoroacetic acid/triisopropylsilane/phenol/H2O (90/2/4/4) gives the 4-pyrrole phenylacyl peptide (3). However, cleavage of 4-pyrrole phenylacyl Rink-appended peptide (7) containing Arg(Pbf) using the same reagents furnishes the 4-pyrrolidine phenylacyl peptide (8), which contains the reduced pyrrole ring. Compound 8 displays a Ki of 2.32 microM, approximately fivefold less potent than compound 3.
Lee
Jung Hwan
JH
The Albert Einstein College of Medicine, Department of Biochemistry, 1300 Morris Park Ave., Bronx, NY 10461, USA. jhlee2000@hanmail.net
D000595:Amino Acid Sequence; D007202:Indicators and Reagents; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D010084:Oxidation-Reduction; D010636:Phenols; D011493:Protein Kinase C / Q000037:antagonists & inhibitors*; D051571:Protein Kinase C-alpha; D011759:Pyrrolidines / Q000737:chemistry*
D007202:Indicators and Reagents; D009842:Oligopeptides; D010636:Phenols; D011759:Pyrrolidines; D011493:Protein Kinase C; D051571:Protein Kinase C-alpha