Synthesis of enediyne peptidomimetics by Passerini reaction (CROSBI ID 647099)
Prilog sa skupa u zborniku | sažetak izlaganja sa skupa | domaća recenzija
Podaci o odgovornosti
Glavaš, Mladena ; Gredičak, Matija ; Jerić, Ivanka
engleski
Synthesis of enediyne peptidomimetics by Passerini reaction
A significant area of organic chemistry is chemical synthesis performed through one–pot mode. [1] Such reactions, known as multicomponent reactions comprise three or more starting reagents and give a single product. The main advantage of multicomponent reactions are an easy access to libraries of complex and structurally diverse compounds starting from relatively simple components. Isocyanide–based multicomponent reactions, e.g. Passerini and Ugi reactions are of special importance, because they provide diverse peptide-like compounds. The Passerini reaction is one of the oldest multicomponent reaction used for the construction of α- acyloxyamides–depsipeptides. The reaction involves coupling of aldehyde, carboxylic acid and isocyanide in a nonpolar solvent. [2] We are interested in utilizing multicomponent reactions for the synthesis of conformationally constrained peptidomimetics. The enediyne structural motif (Figure 1) found in natural products with strong anticancer activity [3] was shown to induce β-turn or β-sheet conformation when incorporated into peptides. Therefore, we decided to use the Passerini reaction for the synthesis of a new class of enediyne-based depsipeptides. Enediyne aldehyde 1, prepared by two consecutive Sonogashira reactions, was coupled with different isocyanides and carboxylic acid in dichloromethane on room temperature (Figure 1). Enediyne depsipeptides 2 were obtained in up to 92 % yields.
multicomponent reactions ; Passerini reaction ; enediynes
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Podaci o prilogu
134-134.
2017.
objavljeno
Podaci o matičnoj publikaciji
25. Hrvatski skup kemičara i kemijskih inženjera s međunarodnim sudjelovanjem ; 3. simpozij Vladimir Prelog : knjiga sažetaka = 25th Croatian Meeting of Chemist and Chemical Engineers with international participation. 3rd symposium “Vladimir Prelog” : Book of Abstracts
Šantić, Ana ; Đaković, Marijana
Zagreb: Hrvatsko društvo kemijskih inženjera i tehnologa (HDKI) ; Hrvatsko kemijsko drustvo
978-953-552327-7
Podaci o skupu
25. Hrvatski skup kemičara i kemijskih inženjera s međunarodnim sudjelovanjem ; 3. simpozij Vladimir Prelog = 25th Croatian Meeting of Chemist and Chemical Engineers with international participation. 3rd symposium “Vladimir Prelog”
poster
12.04.2017-22.04.2017
Poreč, Hrvatska