82597-82-8Relevant articles and documents
Oxidative couplings on tryptophan-based diketopiperazines leading to fused and bridged chemotypes
Mendive-Tapia, Lorena,Albornoz-Grados, Arantxa,Bertran, Alexandra,Albericio, Fernando,Lavilla, Rodolfo
supporting information, p. 2740 - 2743 (2017/03/10)
New chemotypes are obtained from tryptophan-containing diketopiperazines through selective C-C or C-N intramolecular oxidative couplings. The choice of the oxidant source dictates the outcome of the reaction.
A Mutasynthesis Approach with a Penicillium chrysogenum ΔroqA Strain Yields New Roquefortine D Analogues
Ouchaou, Kahina,Maire, Florian,Salo, Oleksandr,Ali, Hazrat,Hankemeier, Thomas,Van Der Marel, Gijsbert A.,Filippov, Dmitri V.,Bovenberg, Roel A. L.,Vreeken, Rob J.,Driessen, Arnold J. M.,Overkleeft, Herman S.
, p. 915 - 923 (2015/04/14)
Penicillium chrysogenum, which lacks the roqA gene, processes synthetic, exogenously added histidyltryptophanyldiketopiperazine (HTD) to yield a set of roquefortine-based secondary metabolites also produced by the wild-type strain. Feeding a number of synthetic HTD analogues to the ΔroqA strain gives rise to the biosynthesis of a number of new roquefortine D derivatives, depending on the nature of the synthetic HTD added. Besides delivering semisynthetic roquefortine analogues, the mutasynthesis studies presented here also shed light on the substrate preferences and molecular mechanisms employed by the roquefortine C/D biosynthesis gene cluster, knowledge that may be tapped for the future development of more complex semisynthetic roquefortine-based secondary metabolites.
Efficient synthesis of 2,5-diketopiperazines using microwave assisted heating
Tullberg, Marcus,Gr?tli, Morten,Luthman, Kristina
, p. 7484 - 7491 (2007/10/03)
In this study a general, efficient and environmentally benign solution phase synthesis of 2,5-diketopiperazines (DKPs) using microwave assisted heating in water is described. A series of 11 structurally different DKPs have been synthesized from dipeptide methyl esters. A range of common laboratory solvents have been tested as well as different reaction times and temperatures. Both classic thermal and microwave assisted heating have been investigated. Microwave assisted heating for 10 min using water as solvent proved, by far, to be the most efficient method of cyclization giving moderate to excellent yields (63-97%) of DKPs. In contrast to other published procedures, this method seems independent of the amino acid sequence.