Photoactive Barbiturate Receptors:  An Ultimate Lock-and-Key System in Which the Key Unlocks the Lock

• Published in: Organic letters Vol. 9; no. 6; pp. 1077 - 1079
• Main Authors: Lakkakula, Suman, Mitkin, Oleg D, Valiulin, Roman A, Kutateladze, Andrei G
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 15-03-2007
• Subjects: Aminopyrine - chemistry; Aminopyrine - pharmacology; Barbital - chemistry; Barbital - pharmacology; Drug Combinations; Molecular Structure; Photochemistry; Phthalic Acids - chemistry; Phthalic Acids - pharmacology; Quinolizines - chemistry; Receptors, GABA-A - chemistry; Receptors, GABA-A - drug effects; Receptors, GABA-A - metabolism; Sulfur Compounds - chemistry
• ISSN: 1523-7060; 1523-7052
• DOI: 10.1021/ol0700153

Conditional photofragmentation is achieved with binary systems incorporating the isophthaloyl bis-aminopyridine barbiturate recognition motif and dithiane- or trithiane-based photolabile modules, which cleave only in the presence of an external sensitizer. The components of the host−guest molecular recognition pair were each outfitted with either the sensitizer or the photocleavable module. In these pairs, photoinduced fragmentation is contingent on a molecular recognition event, which brings the sensitizer into the immediate proximity of the photolabile latch.