Cycloleucine

Fixed

320 ° C

Risk

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Cycloleucine a nonproteinogenic α - amino acid and can be considered as a derivative of the cyclic Norleucins. From this it differs inter alia by a lower order two hydrogen atoms molar mass. The defining structural element is a cyclopentane ring. The α - carbon atom is also no stereogenic center, cycloleucine is therefore not chiral.

Properties

Similarly, like other amino acids cycloleucine is predominantly as a zwitterion before, the formation of which is formally explained by the fact that the proton of the carboxyl group migrates to the free electron pair of the nitrogen atom of the amino group.

In an electric field, the zwitterion migrates not because it is not loaded as a whole. Strictly speaking, this is at the isoelectric point ( at a certain pH value) of the case where the cycloleucine has its lowest solubility in water.

Synthesis

The basic hydrolysis of the heterocycle cyclopentane spiro -5' -hydantoin followed by neutralization with hydrochloric acid gives cycloleucine. The cyclization of NCCH2CO2C2H5 with 1,4- Dibromobutane in the presence of sodium hydride provides 1- Isonitrilocyclopentancarbonsäureethylester. Acid hydrolysis with alcoholic hydrochloric acid and neutralization with alcoholic sodium hydroxide solution then leads to cycloleucine. Alternative synthesis methods are described in another paper.

Use

Cycloleucine is a non-metabolizable amino acid and a specific and reversible inhibitor of enzymes that methylate the nucleic acids. Therefore, it can be used in diverse biochemical experiments.