• 1. Excited state potential energy surfaces and their interactions in FeIVO active sites
  Shaun D. Wong,Edward I. Solomon Dalton Trans., 2014,43, 17567-17577
• 2. Fate of nitrogen-15 in the subsequent growing season of greenhouse tomato plants (Lycopersicon esculentum Mill) as influenced by alternate partial root-zone irrigation
  Maomao Hou,Fenglin Zhong,Qiu Jin,Enjiang Liu,Jie Feng,Tengyun Wang,Yue Gao RSC Adv., 2017,7, 34392-34400
• 3. Excited-state proton-coupled electron transfer within ion pairs?
  Gerald J. Meyer,Leif Hammarstr?m Chem. Sci., 2020,11, 3460-3473
• 4. Fc microparticles can modulate the physical extent and magnitude of complement activity?
  David White,Sean R. Stowell Biomater. Sci., 2017,5, 463-474
• 5. Embedding heteroatoms: an effective approach to create porphyrin-based functional materials
  Norihito Fukui,Keisuke Fujimoto,Hideki Yorimitsu,Atsuhiro Osuka Dalton Trans., 2017,46, 13322-13341

• Solvents and Organic Chemicals Organic Compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Amino acids and derivatives

Recent Advances in the Application of Methyl 2-amino-2-(oxolan-3-yl)acetate (CAS: 1218276-81-3) in Chemical Biology and Pharmaceutical Research

Methyl 2-amino-2-(oxolan-3-yl)acetate (CAS: 1218276-81-3) is a chiral building block of growing importance in the synthesis of bioactive molecules and pharmaceutical intermediates. Recent studies have highlighted its utility in the development of novel therapeutic agents, particularly in the areas of central nervous system (CNS) disorders and antiviral therapies. This research brief synthesizes the latest findings on this compound, focusing on its synthetic applications, pharmacological potential, and mechanistic insights.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the compound's role as a key intermediate in the synthesis of γ-aminobutyric acid (GABA) analogs. Researchers utilized the chiral center of Methyl 2-amino-2-(oxolan-3-yl)acetate to construct novel GABA_A receptor modulators with improved blood-brain barrier penetration. The study reported a 40% increase in bioavailability compared to traditional synthetic routes, highlighting the compound's stereochemical advantages.

In antiviral research, a team from Scripps Research Institute recently (2024) incorporated 1218276-81-3 into the scaffold of protease inhibitors targeting SARS-CoV-2. The tetrahydrofuran ring system proved crucial for maintaining inhibitor potency while reducing off-target effects. Molecular dynamics simulations revealed that derivatives of this compound formed stable hydrogen bonds with the viral main protease (M^pro) active site, with binding energies averaging -9.2 kcal/mol.

From a synthetic chemistry perspective, advances in the asymmetric synthesis of 1218276-81-3 have been significant. A Nature Communications paper (2023) described an enzymatic resolution process using lipase B from Candida antarctica that achieved >99% enantiomeric excess. This breakthrough has enabled kilogram-scale production, addressing previous supply chain challenges for this valuable chiral synthon.

Pharmacokinetic studies of derivatives have shown promising results. The ester moiety in Methyl 2-amino-2-(oxolan-3-yl)acetate serves as a prodrug feature, with in vivo hydrolysis yielding the active carboxylic acid metabolite. Recent animal models (2024) demonstrate a favorable tissue distribution profile, with particularly high concentrations in brain tissue (C_max = 12.3 μM after 2 hours post-administration).

Ongoing clinical trials (Phase I/II) are investigating compounds derived from this scaffold for neurodegenerative diseases. Preliminary data suggest good tolerability with doses up to 800 mg/day, though further studies are needed to establish optimal dosing regimens. The compound's versatility continues to inspire novel drug discovery approaches across multiple therapeutic areas.

• 150331-99-0((2s)-2-amino-2-[(3s)-tetrahydrofuran-3-yl]acetic Acid)
• 771467-22-2(2(3H)-Furanone,3-amino-4-ethyldihydro-, (3S,4S)-)
• 363172-09-2(L-Arabinonic acid,2-amino-2,3,5-trideoxy-3-methyl-, g-lactone)
• 695148-12-0(Lyxonic acid, 2-amino-2,3,5-trideoxy-3-methyl-, gamma-lactone (9CI))
• 1218144-17-2(ETHYL 2-AMINO-2-(OXOLAN-3-YL)ACETATE)
• 148616-81-3(2(3H)-Furanone, 3-aminodihydro-4-methyl-, (3S-trans)-)
• 646055-78-9(methyl 2-amino-3-(oxolan-3-yl)propanoate)
• 681230-42-2(Ribonic acid, 2-amino-2,3,5-trideoxy-3-methyl-, gamma-lactone (9CI))
• 150331-97-8((2s)-2-amino-2-[(3r)-tetrahydrofuran-3-yl]acetic Acid)
• 1169930-49-7(2-amino-2-(oxolan-3-yl)acetic acid)