220573-79-5Relevant academic research and scientific papers
Intramolecular opening of β-lactams with amines as a strategy toward enzymatically or photochemically triggered activation of lactenediyne prodrugs
Banfi, Luca,Guanti, Giuseppe,Rasparini, Marcello
, p. 1319 - 1336 (2007/10/03)
In order to develop a general strategy for selective activation of designed enediyne prodrugs belonging to the "lactenediyne" family, we studied the scope of intramolecular transamidation of simple monocyclic β-lactams bearing a tethered amine. The effect of substituents, of reaction media, and of the type of tether, on the rate of transamidation is disclosed. The possibility of triggering the transamidation event under mild conditions by the action of suitable enzymes or UV light was demonstrated on model monocyclic β-lactams. Finally, the strategy of intramolecular opening of the β-lactam leading to a larger seven-membered ring was employed on a lactenediyne, demonstrating that ring enlargement could unleash the reactivity of the enediyne moiety. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
Intramolecular transamidation of β-lactams as a means for the enzymatic control of ring opening: Effect of substituents on the rate of reaction
Banfi, Luca,Guanti, Giuseppe,Rasparini, Marcello
, p. 9539 - 9542 (2007/10/03)
A series of simple monocyclic β-lactams bearing side-chains, containing amino groups, have been synthesized, and the rate of their intramolecular transamidation studied. Protection of the amino group with an enzymatically cleavable group, allows us to selectively control the ring enlargement process.
