ChemicalBook CAS DataBase List L-Tryptophan

L-Tryptophan synthesis

9synthesis methods

Product Name:L-Tryptophan
CAS Number:73-22-3
Molecular formula:C11H12N2O2
Molecular Weight:204.23

The most attractive production processes for tryptophan are based on microorganisms used as enzyme sources or as overproducers: Enzymatic production from various precursors; Fermentative production from precursors; Direct fermentative production from carbohydrates by auxotrophic and analogue resistant regulatory mutants. L-tryptophan is synthesized from indole, pyruvate, and ammonia by the enzyme tryptophanase or from indole and L-serine/D,L-serine by tryptophan synthase these process variants were not economic due to the high costs of the starting materials. The microbial conversion of biosynthetic intermediates such as indole or anthranilic acid to L-tryptophan has also been considered as alternative for production.
However, the manufacturer using genetically modified strains derived fromBacillus amyloliquefaciens IAM 1521 was forced to stop Ltryptophan production. L-Tryptophan produced by this process was stigmatized because of side products found in the product causing a new severe disease termed eosinophilia-myalgia syndrome (EMS). One of the problematic impurities, "Peak E", was identified as 1,10-ethylidene- bis-(L-tryptophan), a product formed by condensation of one molecule acetaldehyde with two molecules of tryptophan.

1218-34-4 Synthesis

1218-34-4
391 suppliers
$10.00/1g

73-22-3
976 suppliers
$5.00/250mg

Yield:73-22-3 98%

Reaction Conditions:

with pepsin immobilized on terephthalaldehyde functionalized chitosan magnetic nanoparticle in acetonitrile at 20; pH=2; for 48 h;

Steps:

Deacetylation of Amides

General procedure: To a solution of an amide (1 mmol) in 10 mL of acetonitrile and 10 mLof citrate buffer (pH = 2.0) was added the catalyst (100 mg). The reactionmixture was stirred at rt, and the progress of the reaction was monitored byTLC using ethyl acetate/n-hexane 50:50 as the eluent. After 48 h, the catalystswere removed and washed with HCl (0.01M). The crude residue was purifiedby preparative silica gel plate chromatography using ethyl acetate/n-hexane 50:50 as the eluent. The recovered catalyst was used for the next reaction cycleby the same procedure described above.

References:

Lakouraj, Moslem Mansour;Maashsani, Azita;Norouzian, Rafieh-Sadat;Mohadjerani, Maryam [Journal of Carbohydrate Chemistry,2015,vol. 34,# 2,p. 103 - 119]