L(-)-Pipecolinic acid

Chemical properties

white to light yellow crystal powde

The Uses of L(-)-Pipecolinic acid

Pipecolic acid is involved in synaptic transmission in the central nervous system. The l-form occurs in plants.

The Uses of L(-)-Pipecolinic acid

L-Pipecolinic acid is involved in synaptic transmission in the central nervous system. It is also used as pharmaceutical intermediate.

Definition

ChEBI: A pipecolate that is the conjugate acid of L--pipecolic acid.

General Description

Occurs in seeds, malt, edible mushrooms, fruits, etc.

Biochem/physiol Actions

L-pipecolic acid is implicated in Zellweger syndrome. Pipecolic acid is also a plant defence metabolite. It is a signaling compound essential for systemic acquired resistance (SAR).

Preparation

l-Pipecolic acid is an important rigid cyclic nonprotein amino acid, which is obtained through the conversion of l-lysine catalyzed by l-lysine cyclodeaminase (LCD).

Purification Methods

It crystallises from water. The (±)-picrate has m 158-159o (from EtOH or C6H6). [Beilstein 22 H 7, 22 III/IV 97, 22/1 V 220.] The R(+)-enantiomer [1723-00-8] has m 277o(dec) and [] D 20 +27o (c 4, H2O), and the S(-)-enantiomer [3105-95-1] has m 277o(dec) and [] D 20 -26o (c 4, H2O).[cf p 603, Beilstein 22 III/IV 96, 22/1 V 220.]