925893-26-1

Usage

Uses

Used in Pharmaceutical Industry:
Baclofen is used as a medication for treating muscle spasticity and symptoms associated with multiple sclerosis. Its application is based on its ability to act as a GABAB receptor agonist, which helps alleviate muscle stiffness and spasms, providing relief to patients suffering from these conditions.
Used in Neurological Treatments:
As a GABAB receptor agonist, baclofen is utilized in the management of neurological disorders characterized by muscle spasticity. Its role in inhibiting specific signals in the central nervous system makes it a valuable asset in the treatment of such conditions, offering an effective therapeutic option for patients under the guidance of healthcare professionals.

Upstream product

• 1111092-21-7 (1R,2S,5R,8S,1'S)-5-(1'-hydroxy-o-chlorobenzyl)-1,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.0(2,7)]undec-6-en-4-one 
• 89-98-5 2-chloro-benzaldehyde 
• 56-40-6 glycine 

Relevant academic research and scientific papers

A new d-threonine aldolase as a promising biocatalyst for highly stereoselective preparation of chiral aromatic β-hydroxy-α-amino acids

d-Threonine aldolase is an enzyme belonging to the glycine-dependent aldolases, and it catalyzes the reversible aldol reaction of glycine and acetaldehyde to give d-threonine and/or d-allo-threonine. In this study, a putative d-threonine aldolase gene from Delftia sp. RIT313 was cloned and expressed in Escherichia coli BL21 (DE3). The purified enzyme (DrDTA, 47 KDa) exhibited 21.3 U mg-1 activity for the aldol addition of glycine and acetaldehyde in MES-NaOH buffer (pH 6.0) at 50 °C. Both pyridoxal 5′-phosphate and metal ions were needed for the reaction, and the existence of the metal ions enhanced the stability of the enzyme. It was found that the conversion and Cβ-stereoselectivity were dramatically influenced by the reaction temperature, co-solvent, amount of enzyme and reaction time, and it is possible to enable the reaction under kinetic control to retain suitable conversion and high stereoselectivity at the β-carbon, thus tackling the "Cβ-stereoselectivity problem". DrDTA showed high activity toward aromatic aldehydes with electron-withdrawing substituents. Under the optimized reaction conditions, phenylserines with a 2′-fluoro- or 3′-nitro-substituent were obtained with >90% conversion and >90% de. In addition, dl-threo-phenylserine and dl-threo-4-(methylsulfonyl)phenylserine were efficiently resolved with an excellent enantiomeric excess value (ee, >99%) using a whole cell biocatalyst in a two-phase system at 1.0 M and 0.3 M, respectively, the highest substrate concentration reported so far. These results suggested that DrDTA might be a promising biocatalyst for producing chiral aromatic β-hydroxy-α-amino acids.

Diastereo- And enantioselective synthesis of β-Hydroxy-α-amino acids: Application to the synthesis of a key intermediate for lactacystin

The development of a highly efficient and stereoselective methodology for the preparation of β-hydroxy-α- amino acids is described. Nucleophilic addition of enolates of tricyclic iminolactones 1a and 1b to aldehydes in the presence of 6 equiv of lithium chloride in THF at -78 °C leads to aldol adducts in good yield (63-86%) and high diastereoselectivity (up to >25:1 dr). Subsequently, hydrolysis of the aldol adducts under acidic conditions leads to the corresponding β-hydroxy-a-amino acids in good yields (up to 83%) and excellent enantiomeric excesses (99% ee) with good recovery yields of the chiral auxiliaries 6 and 7. This methodology was applied to the facile synthesis of the key intermediate for lactacystin along with several isomers.