Norleucine

• (S ) - ( )-2- aminohexanoic acid
• L ( ) - α - amino caproic acid
• ( S) - ( )- norleucine
• (S)- norleucine
• L- norleucine

Colorless leaflets

Fixed

301 ° C ( decomposition)

Poorly in water ( 16 g · l-1 at 23 ° C)

Attention

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Norleucine is a non- proteinogenic chiral α -amino acid and was discovered by Adolf Weil. There are two enantiomers, L- norleucine [ Synonym: (S)- norleucine ], and D - norleucine [ Synonym: (R)- norleucine ]. Structurally, norleucine derives by substituting an α - hydrogen atom by an amino group (-NH2) of caproic acid. Norleucine belongs together with its constitutional isomers of leucine, isoleucine, and tert- leucine to the group of leucine.

Representation

The racemate is obtained by reaction of 2- bromohexanoic with NH3 in aqueous solution ( 50 ° C, 30 h).

Use

Norleucine is used for experimental studies of protein structures and functions. Aminoacyl -tRNA synthetases may be deceived, by offering them instead of their normal substrates certain non-biological amino acids. So ethionine and norleucine be installed in such positions in proteins that would normally take methionine.