Cas no 171557-31-6 (2-(Bis(2-(tert-butoxy)-2-oxoethyl)amino)acetic acid)

2-(Bis(2-(tert-butoxy)-2-oxoethyl)amino)acetic acid is a specialized tert-butyl ester-protected amino acid derivative, primarily used in peptide synthesis and organic chemistry applications. Its key advantages include the presence of tert-butoxycarbonyl (Boc) protecting groups, which enhance stability under basic conditions and facilitate selective deprotection under mild acidic conditions. The compound’s structure allows for controlled functionalization, making it valuable in the synthesis of complex molecules. Its high purity and well-defined reactivity profile ensure consistent performance in coupling reactions. This reagent is particularly useful in solid-phase peptide synthesis (SPPS) and other methodologies requiring orthogonal protection strategies.
2-(Bis(2-(tert-butoxy)-2-oxoethyl)amino)acetic acid structure
171557-31-6 structure
Product Name:2-(Bis(2-(tert-butoxy)-2-oxoethyl)amino)acetic acid
CAS No:171557-31-6
MF:C14H25NO6
MW:303.351404905319
MDL:MFCD09833730
CID:1033271
PubChem ID:10542461
Update Time:2025-06-09

2-(Bis(2-(tert-butoxy)-2-oxoethyl)amino)acetic acid Chemical and Physical Properties

Names and Identifiers

    • 2-(Bis(2-(tert-butoxy)-2-oxoethyl)amino)acetic acid
    • (BIS-TERT-BUTOXYCARBONYLMETHYL-AMINO)-ACETIC ACID
    • N,N-Bis[2-(tert-butoxy)-2-oxoethyl]glycine
    • Glycine, N,N-bis[2-(1,1-diMethylethoxy)-2-oxoethyl]-
    • [Bis(2-tert-butoxy-2-oxoethyl)amino]acetic acid
    • DA-18104
    • DS-5678
    • MFCD09833730
    • PD197118
    • 2-[Bis[2-(tert-butoxy)-2-oxoethyl]amino]acetic Acid
    • bis(tert-butoxycarbonylmethyl)aminoacetic acid
    • DEUFNPOTWJNGNL-UHFFFAOYSA-N
    • 171557-31-6
    • N,?N-?bis[2-?(1,?1-?dimethylethoxy)?-?2-?oxoethyl]?-glycine
    • 2-(Bis(2-(tert-butoxy)-2-oxoethyl)amino)aceticacid
    • SCHEMBL419703
    • CS-W021426
    • HY-W040686
    • DTXSID00441555
    • SY114315
    • A881922
    • {BIS[2-(TERT-BUTOXY)-2-OXOETHYL]AMINO}ACETIC ACID
    • 2-[bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]acetic acid
    • AKOS005068269
    • MDL: MFCD09833730
    • Inchi: 1S/C14H25NO6/c1-13(2,3)20-11(18)8-15(7-10(16)17)9-12(19)21-14(4,5)6/h7-9H2,1-6H3,(H,16,17)
    • InChI Key: DEUFNPOTWJNGNL-UHFFFAOYSA-N
    • SMILES: O(C(CN(CC(=O)O)CC(=O)OC(C)(C)C)=O)C(C)(C)C

Computed Properties

  • Exact Mass: 303.16825
  • Monoisotopic Mass: 303.16818752g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 7
  • Heavy Atom Count: 21
  • Rotatable Bond Count: 10
  • Complexity: 361
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: -0.6
  • Topological Polar Surface Area: 93.1?2

Experimental Properties

  • Density: 1.129
  • PSA: 93.14

2-(Bis(2-(tert-butoxy)-2-oxoethyl)amino)acetic acid Security Information

2-(Bis(2-(tert-butoxy)-2-oxoethyl)amino)acetic acid Pricemore >>

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Additional information on 2-(Bis(2-(tert-butoxy)-2-oxoethyl)amino)acetic acid

Recent Advances in the Application of 2-(Bis(2-(tert-butoxy)-2-oxoethyl)amino)acetic acid (CAS: 171557-31-6) in Chemical Biology and Pharmaceutical Research

The compound 2-(Bis(2-(tert-butoxy)-2-oxoethyl)amino)acetic acid (CAS: 171557-31-6) has recently garnered significant attention in the field of chemical biology and pharmaceutical research due to its versatile applications in drug discovery and development. This research briefing aims to provide an overview of the latest findings related to this compound, focusing on its synthesis, mechanism of action, and potential therapeutic applications.

Recent studies have highlighted the role of 2-(Bis(2-(tert-butoxy)-2-oxoethyl)amino)acetic acid as a key intermediate in the synthesis of peptide-based therapeutics. Its unique structural features, including the tert-butoxy groups, make it an ideal candidate for protecting amino acids during solid-phase peptide synthesis (SPPS). A 2023 study published in the Journal of Medicinal Chemistry demonstrated its efficacy in improving the yield and purity of complex peptide sequences, particularly those targeting G-protein-coupled receptors (GPCRs).

In addition to its synthetic utility, this compound has shown promise in the development of novel prodrugs. Research conducted at the University of Cambridge in 2024 revealed that 2-(Bis(2-(tert-butoxy)-2-oxoethyl)amino)acetic acid can be used to enhance the bioavailability of poorly soluble drugs by forming ester prodrugs. The study reported a 2.5-fold increase in oral absorption for a model anticancer drug when conjugated with this compound, suggesting its potential for improving drug delivery systems.

Another significant advancement involves the application of this compound in targeted drug delivery. A team at MIT recently developed a nanoparticle-based system where 2-(Bis(2-(tert-butoxy)-2-oxoethyl)amino)acetic acid serves as a linker between the nanoparticle core and therapeutic payload. This system demonstrated enhanced tumor targeting and reduced off-target effects in preclinical models of breast cancer, as reported in Nature Nanotechnology (2024).

From a mechanistic perspective, computational studies have provided insights into the molecular interactions of this compound. Molecular dynamics simulations published in the Journal of Chemical Information and Modeling (2023) revealed that the tert-butoxy groups contribute to the compound's stability in physiological conditions while allowing for controlled release of active pharmaceutical ingredients through enzymatic cleavage.

Looking forward, researchers are exploring the potential of 2-(Bis(2-(tert-butoxy)-2-oxoethyl)amino)acetic acid in emerging areas such as PROTAC (proteolysis-targeting chimera) technology and antibody-drug conjugates (ADCs). Preliminary results from a collaboration between Pfizer and Stanford University suggest that this compound could serve as an effective linker in next-generation ADCs, with improved stability and reduced immunogenicity compared to current technologies.

In conclusion, the growing body of research on 2-(Bis(2-(tert-butoxy)-2-oxoethyl)amino)acetic acid (CAS: 171557-31-6) underscores its importance as a multifunctional tool in modern pharmaceutical research. Its applications span from synthetic chemistry to advanced drug delivery systems, making it a compound of significant interest for future therapeutic development. Continued research in this area is expected to yield further innovations in drug design and delivery strategies.

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