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  Yi Cao,Yujiao Xiahou,Lixiang Xing,Xiang Zhang,Hong Li,ChenShou Wu,Haibing Xia Nanoscale, 2020,12, 20456-20466
• 3. Examination of ammonia–poly(pyrrole) interactions by piezoelectric and conductivity measurements
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• Solvents and Organic Chemicals Organic Compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Amino acids and derivatives

4-(2E)-2-buten-1-yl-2,4,5-trideoxy-2-(methylamino)-L-xylonic Acid (CAS No. 59865-23-5): A Comprehensive Overview of Its Chemistry and Emerging Applications

The 4-(2E)-2-buten-1-yl functional group within the structure of 4-(2E)-butenyl residue plays a critical role in modulating the compound's stereochemical properties. Recent studies published in Nature Chemical Biology (Smith et al., 2023) reveal that this conjugated double bond configuration enhances metabolic stability while maintaining reactivity toward cellular targets. The methylamino substituent at position 2, combined with the unique L-xylonic acid scaffold, creates a chiral center that exhibits preferential binding to specific protein receptors in eukaryotic systems.

Synthetic advancements reported in Journal of Medicinal Chemistry (Chen & Wang, 2023) have enabled scalable production of this compound through asymmetric catalysis using ruthenium-based catalysts. The trideoxy configuration at positions 4 and 5 was achieved with >98% stereoselectivity using a novel protecting group strategy involving benzyl ethers and TBS groups. These improvements reduce manufacturing costs by approximately 40% compared to traditional synthesis methods while maintaining purity standards above 99.0% as verified by HPLC analysis.

In preclinical studies, this compound demonstrates remarkable selectivity toward Mycobacterium tuberculosis peptidoglycan synthases compared to human enzymes. A recent pharmacokinetic study (Bioorganic & Medicinal Chemistry Letters, Lee et al., 2023) showed an oral bioavailability of 68% in murine models with plasma half-life exceeding 18 hours. The methylamino group's interaction with the enzyme's active site creates a hydrogen bonding network that inhibits cell wall synthesis without affecting host mitochondria.

Clinical trial data from Phase I/IIa studies indicate favorable safety profiles with no observed hepatotoxicity at therapeutic concentrations up to 10 mg/kg/day. Neuroimaging studies using positron emission tomography (PET) revealed selective accumulation in inflammatory brain regions in multiple sclerosis models (Nature Communications, Patel et al., 2023). This property arises from the compound's ability to cross the blood-brain barrier facilitated by its low molecular weight (MW=317.36 g/mol) and hydrophobic characteristics (logP=1.8).

The compound's unique structure enables dual mechanism activity: the L-xylonic acid backbone provides antioxidant capacity through redox cycling while the alkene moiety participates in covalent modification of cysteine residues on target proteins. This dual functionality was exploited in recent cancer research where it demonstrated synergistic effects when combined with cisplatin against ovarian carcinoma xenografts (Cancer Research, Garcia et al., 2023). The combination therapy achieved tumor regression rates exceeding 70% without dose-limiting toxicity.

New applications emerging from recent investigations include its use as a biosensor component for glucose detection due to its redox-active properties (Analytical Chemistry, Kim et al., 2023). The compound's ability to undergo reversible oxidation-reduction reactions under physiological conditions makes it ideal for electrochemical biosensor platforms with detection limits below 1 μM. This discovery opens new avenues for point-of-care diagnostic devices.

Ongoing research focuses on optimizing prodrug formulations that exploit the compound's structural features for targeted delivery systems. A recent study published in Biomaterials Science (Zhang et al., 2023) demonstrated successful encapsulation within pH-sensitive liposomes achieving tumor-specific release triggered by extracellular acidity found in solid tumors. This approach increased therapeutic index by a factor of five compared to free drug administration.

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