A convenient strategy of dimerization by microwave heating and using 2,5-diketopiperazine as scaffold

Tetrahedron Letters

Volumn 44, Issue 6, 2003, Pages 1145-1148

  Santagada, Vincenzo ^a   Fiorino, Ferdinando ^a   Perissutti, Elisa ^a   Severino, Beatrice ^a   Terracciano, Sara ^a   Cirino, Giuseppe ^a   Caliendo, Giuseppe ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

Dimerization; Microwave irradiation in solution; Synthesis of diketopiperazine

Indexed keywords

2,5 PIPERAZINEDIONE; CHEMICAL COMPOUND; PEPTIDE; PIPERAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL INTERACTION; CHEMICAL REACTION; COMPARATIVE STUDY; DIMERIZATION; EPIMERIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IRRADIATION; MASS SPECTROMETRY; MICROWAVE COOKING; SYNTHESIS;

EID: 0037415511     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02836-8     Document Type: Article

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46. -1. The final heptapeptide was characterized by mass spectrometry (LCQ Thermoquest-Ion Trap) and the data were consistent with the considered structure.
47. 4), was crystallized from appropriate solvents or purified by column chromatography.
48. 2O was added to the solution until the product precipitated. The crude product was purified by preparative RP-HPLC as reported in Ref. 25.
49. Removal of Fmoc-protecting group: Standard cleavage procedure was used to remove Fmoc protecting group. The peptide (1 mmol) was dissolved in 20% piperidine/DMF (15 ml) and the reaction was allowed to proceed at room temperature for 45 min. The solvent was evaporated in vacuo, the residue was triturated with diethyl ether (25 ml), the solid was collected, washed with diethyl ether, and dried in vacuo.
50. 25 successively purified by RP-HPLC and characterized by LCQ Ion-Trap mass spectrometer.
51. 2)-Leu-Gly-OH derivatives (3.16 mmol), DMAP (4-(dimethylamino)pyridine, 3.47 mmol) and HBTU (3.47 mmol) in 6 mL anhydrous DMF was treated by microwave irradiation for 5 or 8 min, respectively (UV, 400 W, 40°C) or by conventional heating for 24 h at 40°C, respectively. The reaction mixture was separated from the solvent, the crude residue was taken up in ethyl acetate and washed successively three times with citric acid (5%), sodium bicarbonate (5%), and a saturated solution of sodium chloride. The final crude products, after removal of the Boc and Pbf protecting groups (Scheme 1a), were purified and characterized by preparative RP-HPLC as reported in Ref. 25.