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102522-32-7
Octanoic acid, 8-amino-, 1,1-dimethylethyl ester

Catalog#:1P00083Y

CAS:102522-32-7

MDL:MFCD24624132

Molecular Formula:C12H25NO2

Molecular Weight:215.3324

UN Number:

Haz Class:

Packing Group:

Synonyms: 102522-32-7; 8-Aminooctanoic acid tert-butyl ester; A1-08455; TERT-BUTYL 8-AMINOOCTANOATE; Octanoic acid, 8-amino-, 1,1-dimethylethyl ester; 8-aminooctanoic acid tert.-butyl ester; ACMC-20m5hn; SCHEMBL3365775; CTK0G7565; DTXSID90552386; ZINC34186193;

Keywords: 102522-32-7,MFCD24624132,1P00083Y,Octanoic acid, 8-amino-, 1,1-dimethylethyl ester,C12H25NO2

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Catalog# Purity Size Price Dis. Price Availability Quantity
1P00083Y 95% 100mg $47.00 $36.00 In Stock USA ADD TO CART BUY NOW
1P00083Y 95% 250mg $94.00 $71.00 In Stock USA ADD TO CART BUY NOW
1P00083Y 95% 1g $184.00 $138.00 In Stock USA ADD TO CART BUY NOW
1P00083Y 98% 5g $596.00 $447.00 In Stock USA ADD TO CART BUY NOW

  • Octanoic acid, 8-amino-, 1,1-dimethylethyl ester, often referred to as a Boc-protected 8-aminooctanoic acid, is a derivative of amino fatty acids used in the field of organic synthesis and pharmaceutical research. The presence of the tert-butyl (t-Boc) protecting group on the amino functionality is a crucial feature that allows for its various applications.
    
    1. **Peptide Synthesis:**
       The primary application of this compound is in the synthesis of peptides. The Boc-protected amino acid can be used to elongate peptide chains without unwanted side reactions that can occur if the amino group were not protected. Once the peptide synthesis is complete, the Boc group can be selectively removed under acidic conditions to reveal the free amino group for further reactions or for the final deprotection of the synthesized peptide.
    
    2. **Drug Design and Development:**
       Its structure, including the long hydrophobic octanoic acid side chain, makes it valuable in the design of lipidated peptides and drugs, potentially improving their cell membrane permeability and increasing oral bioavailability. The 8-aminooctanoic acid moiety can act as a spacer or hydrophobic linker in drug molecules.
    
    3. **Conjugation to Biomolecules:**
       In the development of bioconjugates, for example in the conjugation of peptides to polymers or the surface modification of nanoparticles, the protected amino group can serve as a site for linking to other molecules while avoiding reactions with the carboxylic acid end.
    
    4. **Synthesis of Amide Bonds:**
       It's also used to form amide bonds with carboxylic acids or their derivatives. Since the amino group is protected, it prevents the formation of polypeptides or oligomeric species, offering chemists the ability to form more selective and controlled amide linkages.
    
    5. **Chiral Pool Synthesis:**
       Boc-8-aminooctanoic acid acts as a chiral building block in the synthesis of complex molecules. The chiral center present in the compound can be used to induce stereochemistry in the resulting synthesized compounds.
    
    6. **Synthesis of Non-natural Amino Acids:**
       It is also utilized as a starting material in the synthesis of non-natural amino acids, which find use in a range of research applications and in the design of novel pharmaceuticals.
    
    In each of these applications, the Boc group serves the invaluable role of protecting the amine, enabling chemical reactions to occur at other sites of the molecule without interference. The t-Boc protection strategy is a cornerstone in modern synthetic organic chemistry, making compounds like Boc-8-aminooctanoic acid essential in various synthesis protocols.

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