635680-16-9

Usage

Uses

Used in Pharmaceutical Industry:
(S)-2-AMINO-8-OXO-DECANOIC ACID, METHYL ESTER is used as a biologically important constituent for the development of cyclic tetrapeptides with potential therapeutic applications. Its presence in apicidins and 9,10-depoxy-chlamydocin highlights its significance in creating bioactive molecules that can be utilized in the treatment of various diseases and conditions.
Used in Research and Development:
In the field of research and development, (S)-2-AMINO-8-OXO-DECANOIC ACID, METHYL ESTER serves as a valuable compound for studying the structure, properties, and potential applications of cyclic tetrapeptides. Its role in the synthesis and modification of these bioactive molecules can lead to the discovery of new drugs and therapeutic agents.
Used in Agrochemical Industry:
(S)-2-AMINO-8-OXO-DECANOIC ACID, METHYL ESTER may also find applications in the agrochemical industry, where cyclic tetrapeptides have shown potential as antimicrobial, antifungal, and insecticidal agents. Its use in this industry can contribute to the development of novel and effective pest control solutions.
Overall, (S)-2-AMINO-8-OXO-DECANOIC ACID, METHYL ESTER is a versatile compound with a wide range of potential applications across various industries, particularly in the development of pharmaceuticals, research, and agrochemicals. Its presence in naturally occurring cyclic tetrapeptides highlights its importance in creating bioactive molecules with therapeutic potential.

InChI:InChI=1/C11H21NO3/c1-3-9(13)7-5-4-6-8-10(12)11(14)15-2/h10H,3-8,12H2,1-2H3/t10-/m0/s1

Upstream product

• 34956-85-9 2-(5-bromopentyl)-2-ethyl-[1,3]-dioxolane 
• 1940-18-7 1-ethylcyclohexanol 
• 2146-62-5 8-bromo-octan-3-one 
• 6621-59-6 6-bromo-1-hexanenitrile 
• 635680-09-0 trans-2-[4-(2-ethyl-[1,3]dioxolan-2-yl)-pentyl]-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine 

Relevant academic research and scientific papers

Design, synthesis, biological evaluation, and structural characterization of potent mistone deacarylase inhibitors based on cyclic α/β- tetrapeptide architectures

Histone deacetylases (HDACs) are a family of enzymes found in bacteria, fungi, plants, and animals that profoundly affect cellular function by catalyzing the removal of acetyl groups from ε-N-acetylated lysine residues of various protein substrates including histones, transcription factors, α-tubulin, and nuclear importers. Although the precise roles of HDAC isoforms in cellular function are not yet completely understood, inhibition of HDAC activity has emerged as a promising approach forreversing the aberrant epigenetic states associated with cancer and oth er chronic diseases. Potent new isoform-selective HDAC inhibitors would therefore help expand our understanding of the HDAC enzymes and represent attractive lead compounds for drug design, especially if combined withhigh-resolution structural analyses of such inhibitors to shed light on the three-dimensional pharmacophoric features necessary for the future design of more potent and selective compounds. Here we present structura l and functional analyses of a series of β acid-containing HDAC inhibitors inspired by cyclic tetrapeptide natural products. To survey a diverse ensemble of pharmacophoric configurations, we systematically varied the position of the β-amino acid, amino acid chirality, functionalization of the Zn2+-coordinating amino acid side chain, and alkylation of the backbone amide nitrogen atoms around the macrocycle. In many cases, the compounds were a single conformation in solution and exhibited potent activities against a number of HDAC isoforms as well as effective antiproliferative and cytotoxic activities against human tumorcells. High-resolution NMR solution structures were determined for a se lection of the inhibitors, providing a useful means of correlating detailed structural information with potency. The structure-based approach described here is expected to furnish valuable insights toward the future design of more selective HDAC inhibitors.

A novel series of potent and selective ketone histone deacetylase inhibitors with antitumor activity in vivo

Histone deacetylase (HDAC) inhibitors offer a promising strategy for cancer therapy, and the first generation HDAC inhibitors are currently in the clinic. Entirely novel ketone HDAC inhibitors have been developed from the cyclic tetrapeptide apicidin. These compounds show class I subtype selectivity and levels of cellular activity comparable to clinical candidates. A representative example has demonstrated tumor growth inhibition in a human colon HCT-116 carcinoma xenograft model comparable to known inhibitors.

Ring-closing metathesis in the synthesis of biologically active peptidomimetics of apicidin A

Syntheses of novel 16-membered macrocyclic peptidomimetics are reported, which employ iterative peptide coupling followed by high yielding ring-closing metathesis (RCM) as the key cyclization step. The target macrocyclic compounds include examples contain

Efficient Syntheses of Biologically Important (S)-2-Amino-8-oxodecanoic Acid (Aoda) and Homologues

The efficient and practical asymmetric syntheses of the biologically important (S)-2-amino-8-oxodecanoic ester and its homologues have been achieved employing the Schoellkopf chiral auxiliary. Carbon-carbon bond formation between the appropriate alkyl bromide and the LDA generated anion of the Schoellkopf auxiliary, followed by hydrolysis provided the desired methyl ester of a long-chained keto amino acid in high yield with high selectivity.