L-Histidine

Description

White, odorless crystals or crystalline powder having a slightly bitter taste. It is soluble in water, very slightly soluble in alcohol, and insoluble in ether. It melts with decomposition between about 277° and 288°C.

Chemical properties

White or almost white, crystalline powder or colourless crystals

Chemical properties

L-Histidine is an odorless powder with slightly bitter taste

Occurrence

Reported found in water bread, macaroni, egg noodles, corn flakes, corn grits, oatmeal, wheat bran, wheat flakes, shredded wheat, barley, brown rice, rye flour, whole grain wheat flour, buttermilk, blue cheese, cheddar cheese, cottage cheese, cream cheese, Parmesan cheese, bacon, cured ham, frankfurters, pork sausage, canned red kidney beans, canned sweet corn, canned peas, canned lima beans, canned potatoes, almonds, cashews, peanuts, dates, beef, lamb, veal, chicken, turkey and other natural sources

The Uses of L-Histidine

L-Histidine is an essential amino acid for human development which the body cannot produce on its own. L-Histidine is one of the 22 proteinogenic amino acids. L-Histidine precursor to histamine (H4365 00) and a component of carnosine.

The Uses of L-Histidine

L-Histidine acts as a precursor to histamine and a component of carnosine. It is also used in medicine, feed additive, biochemical research, dietary supplement. It is used in a nutrition enhancer, is the amino acid fluid infusion. It can be used in the treatment of gastric ulcer.

The Uses of L-Histidine

L-Histidine has been used for characterization of ZnO nanorod in an attempt to develop a technique for the ultra-low level detection of l-histidine.

Definition

ChEBI: The L-enantiomer of the amino acid histidine.

Biotechnological Production

L-Histidine is grouped with the aromatic amino acids, but the metabolic route diverges at an early stage from the other members of the group. It is produced in C. glutamicum in a 10-step sequence starting from phosphoribosyl pyrophosphate. Originally production titers of up to 10.5 g/L were reported, but this has since been increased by workers at Kyowa Hakko to 22.5 g/L. In a parallel development, the fermentation of L-histidine using E. coli has been reported by Ajinomoto, with titers up to 19.1 g/L. Both the titer and the carbon yield for L-histidine are lower than those reported for L-phenylalanine and L-tryptophan, and L-histidine remains one of the more challenging amino acids to produce on an industrial scale.

Biochem/physiol Actions

Precursor of histamine by action of histidine decarboxylase.

Purification Methods

A likely impurity is arginine. S-Histidine is adsorbed from aqueous solution onto a Dowex 50-H+ ion-exchange resin, washed with 1.5M HCl (to remove other amino acids), then eluted with 4M HCl as the dihydrochloride. This purified dihydrochloride (see below) is finally dissolved in water, the pH adjusted to 7.0, and the free zwitterionic base crystallises out on addition of EtOH. Its solubility in H2O is 4.2% at 25o. [Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 pp 1971-1993 1961, Beilstein 25 III/IV 4344.]