86432-28-2

Usage

Uses

Used in Pharmaceutical Synthesis:
(S)-2-Hexanamido-3-(4-hydroxyphenyl)propanoic acid is used as an intermediate in the pharmaceutical industry for the synthesis of various drugs. Its unique structure and functional groups allow for the creation of a wide array of therapeutic compounds.
Used in Asymmetric Synthesis:
In the field of organic chemistry, (S)-2-Hexanamido-3-(4-hydroxyphenyl)propanoic acid is utilized as a chiral auxiliary. This application is crucial for the production of enantiomerically pure compounds, which are essential in the development of more effective and selective medications.
Used in Antioxidant Research:
The 4-hydroxyphenyl group present in (S)-2-Hexanamido-3-(4-hydroxyphenyl)propanoic acid may have antioxidant properties, making it a potential candidate for research and development in the area of antioxidants. These antioxidants can be applied in various industries, such as the food and pharmaceutical sectors, to enhance product shelf life and support human health.
Used in Drug Development:
Due to its potential interactions with biological targets like proteins and enzymes, (S)-2-Hexanamido-3-(4-hydroxyphenyl)propanoic acid can be employed in drug development. It may contribute to the design of novel drugs with improved efficacy and selectivity, ultimately benefiting patients and advancing medical treatments.
Used in Biochemical Applications:
(S)-2-HexanaMido-3-(4-hydroxyphenyl)propanoic acid's ability to interact with biological targets also makes it a valuable tool in various biochemical applications. It can be used in the study of enzyme mechanisms, protein structure, and other biological processes, furthering our understanding of these systems and potentially leading to new therapeutic strategies.

Upstream product

• 1080-06-4 L-Tyr-OMe 
• 1104874-94-3 (S)-methyl 2-(hexanamido)-3-(4-hydroxyphenyl)propanoate 
• 60-18-4 L-tyrosine 
• 142-62-1 hexanoic acid 

Relevant academic research and scientific papers

Repurposing the 3-Isocyanobutanoic Acid Adenylation Enzyme SfaB for Versatile Amidation and Thioesterification

Genome mining of microbial natural products enables chemists not only to discover the bioactive molecules with novel skeletons, but also to identify the enzymes that catalyze diverse chemical reactions. Exploring the substrate promiscuity and catalytic mechanism of those biosynthetic enzymes facilitates the development of potential biocatalysts. SfaB is an acyl adenylate-forming enzyme that adenylates a unique building block, 3-isocyanobutanoic acid, in the biosynthetic pathway of the diisonitrile natural product SF2768 produced by Streptomyces thioluteus, and this AMP-ligase was demonstrated to accept a broad range of short-chain fatty acids (SCFAs). Herein, we repurpose SfaB to catalyze amidation or thioesterification between those SCFAs and various amine or thiol nucleophiles, thereby providing an alternative enzymatic approach to prepare the corresponding amides and thioesters in vitro.

The impact of sugar and fatty acid on the bioactivity of N-fatty acyl-L-tyrosine aglycone

Abstract: In the present study, a series of fatty acids-based (short, medium and long unsaturated chains) glycosylated N-fatty acyl-L-tyrosines and N-lipoyl-L-tyrosine methyl esters were synthesized and evaluated for their cytotoxic and antimicrobial activities. The aglycone moiety was synthesized using different chemical reagents. The glycosylation of aglycone moiety with different carbohydrates was performed using the Lewis acid, BF 3.Et 2O. All the synthesized compounds were tested against a panel of four cancer cell lines. The glycosylated N-fatty acyl-L-tyrosines showed moderate activity against all the cell lines and the IC 50 values were in the range of 15.6-45.6μM. However, the oleic acid analogues (10a, 10d) exhibited IC 50 values of 15.6, 17.6μM, respectively, against MDA-MB-231 cell line. Glycosylated N-lipoyl-L-tyrosine methyl esters (6b–6d) showed promising activity against all the tested cell lines and the IC 50 values ranged between 9.4-13.8μM. The compound 6d exhibited significant cytotoxicity and IC 50 values were 10.5, 9.4, 10.9 and 12.1μM against A549, PC3, MDA-MB-231 and HepG2 cell lines, respectively. Moreover, the non-glycosylated N-fatty acyl-L-tyrosine and methyl N-fatty acyl-L-tyrosinate derivatives showed excellent and moderate antimicrobial activity against some of the tested bacterial strains. Graphical Abstract: The glycosylated N-fatty acyl-L-tyrosines with short, medium and long chain unsaturated fatty acids and glycosylated N-lipoyl-L-tyrosine methyl esters were synthesized and further evaluated for their biological activities to examine the impact of sugar and fatty acid on the bioactivity of N-fatty acyl-L-tyrosine derivatives. [Figure not available: see fulltext.].

Synthetic libraries of tyrosine-derived bacterial metabolites

The preparation of a collection of 131 small molecules, reminiscent of families of long chain N-acyl tyrosines, enamides and enol esters that have been isolated from heterologous expression of environmental DNA (eDNA) in Escherichia coli, is reported. The synthetic libraries of N-acyl tyrosines and their 3-keto counterparts were prepared via solid-phase routes, whereas the enamides and enol esters were synthesized in solution-phase.