Diazotrifluoropropionamido-Containing Prenylcysteines: Syntheses and Applications for Studying Isoprenoid−Protein Interactions
- 14 February 2003
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 5 (5), 609-612
- https://doi.org/10.1021/ol026752a
Abstract
Photoaffinity-labeled prenylcysteines (1 and 2) incorporating a diazotrifluoropropionamide-based photophore have been prepared. Photolyses of 2 in the presence of RhoGDI, a protein that interacts with prenylated proteins, and prenylcysteine-containing competitors demonstrate the effectiveness of this photoaffinity-labeled analogue as a tool for studying isoprenoid binding sites.Keywords
This publication has 17 references indexed in Scilit:
- Synthesis and evaluation of benzophenone-based photoaffinity labeling analogs of prenyl pyrophosphates containing stable amide linkagesBioorganic & Medicinal Chemistry Letters, 1997
- Benzoylphenoxy analogs of isoprenoid diphosphates as photoactivatable substrates for bacterial prenyltransferasesBioorganic & Medicinal Chemistry Letters, 1997
- Photoaffinity Labeling of Yeast Farnesyl Protein Transferase and Enzymatic Synthesis of a Ras Protein Incorporating a Photoactive IsoprenoidBiochemical and Biophysical Research Communications, 1997
- Mammalian Protein Geranylgeranyltransferase-I: Substrate Specificity, Kinetic Mechanism, Metal Requirements, and Affinity LabelingBiochemistry, 1995
- Benzophenone Photophores in BiochemistryBiochemistry, 1994
- Direct conversion of activated alcohols to azides using diphenyl phosphorazidate. A practical alternative to Mitsunobu conditionsThe Journal of Organic Chemistry, 1993
- Clavepictines A and B: cytotoxic quinolizidines from the tunicate Clavelina pictaJournal of the American Chemical Society, 1991
- Studies on Ca2+ channel antagonists. A 2-diazo-3,3,3-trifluoropropionamide derivative related to verapamil as a potential photoaffinity probeJournal of Medicinal Chemistry, 1990
- Reductive lactonization of strategically methylated quinone propionic acid esters and amidesThe Journal of Organic Chemistry, 1989
- Substitution reactions which proceed via radical anion intermediates. 26. Oxidative substitution of nitroparaffin saltsThe Journal of Organic Chemistry, 1983