A mild and straightforward preparation of cysteine-derived 2,5-diketopiperazines (DKPs) is reported, by cyclization of (R)-2,2-dimethyltetrahydrothiazole-4-carboxylic acid hydrochloride or of (R)-tetrahydrothiazole-4-carboxylic acid hydrochloride, mediated by HBTU and DIEA. One DKP has been characterized by X-ray analysis, while the other one has been hydrolyzed to cyclo-Cys-Cys. The preparation of this latter compound as been previously reported by a troublesome and low yielding preparation.
D. Iannotta, N. Castellucci, M. Monari, C. Tomasini (2010). A straightforward synthesis and partial hydrolysis of cysteine-derived 2,5-diketopiperazines. TETRAHEDRON LETTERS, 51, 4558-4559 [10.1016/j.tetlet.2010.06.108].
A straightforward synthesis and partial hydrolysis of cysteine-derived 2,5-diketopiperazines
CASTELLUCCI, NICOLA;MONARI, MAGDA;TOMASINI, CLAUDIA
2010
Abstract
A mild and straightforward preparation of cysteine-derived 2,5-diketopiperazines (DKPs) is reported, by cyclization of (R)-2,2-dimethyltetrahydrothiazole-4-carboxylic acid hydrochloride or of (R)-tetrahydrothiazole-4-carboxylic acid hydrochloride, mediated by HBTU and DIEA. One DKP has been characterized by X-ray analysis, while the other one has been hydrolyzed to cyclo-Cys-Cys. The preparation of this latter compound as been previously reported by a troublesome and low yielding preparation.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
