1-(1-Adamantylcarbonyl)proline (ACA)

Synonyms: ACA, 1-Adamantaneacetyl-L-proline, N-(1-Adamantylcarbonyl)-L-proline, (S)-1-(1-Adamantylcarbonyl)pyrrolidine-2-carboxylic acid, 1-(Tricyclo[3.3.1.1^3,7]dec-1-ylcarbonyl)-L-proline

1-(1-Adamantylcarbonyl)proline, commonly abbreviated as ACA, is a synthetic derivative that couples an adamantane cage with the amino acid L-proline through an amide bond. The adamantane moiety is a tricyclic hydrocarbon known for its remarkable lipophilicity and metabolic stability, while proline contributes a rigid, cyclic secondary amine structure. This combination yields a molecule with unique physicochemical properties that have attracted attention in both medicinal chemistry and materials science.

ACA is not a naturally occurring compound; it is produced via synthetic routes, typically by acylating L-proline with 1-adamantanecarbonyl chloride or a related activated adamantane derivative. The reaction is usually carried out in an aqueous or mixed solvent system under basic conditions, followed by acidification and purification. The resulting product is a white to off-white crystalline solid that is optically active due to the L-proline configuration. Its molecular formula is C15H21NO3, and it has a molecular weight of 263.33 g/mol.

In the pharmaceutical and agrochemical industries, ACA serves as a versatile building block. The adamantane group is well-known for enhancing drug-like properties, such as increasing lipophilicity and improving blood-brain barrier penetration, while the proline moiety can act as a chiral auxiliary or a pharmacophore. ACA has been explored as an intermediate in the synthesis of peptidomimetics, enzyme inhibitors, and receptor ligands. Additionally, its ability to form stable metal complexes makes it useful in coordination chemistry and catalysis.

LyvBio supplies ACA with high purity, typically ≥98% as determined by HPLC. Our production process is optimized to ensure consistent quality, and we provide comprehensive documentation to support your regulatory and research needs. Whether you are developing a new drug candidate or exploring novel materials, ACA offers a reliable and scalable solution.

Function

• Chiral building block: The proline moiety provides a chiral center, making ACA valuable for asymmetric synthesis.
• Lipophilicity enhancer: The adamantane group increases the lipophilic character of target molecules, potentially improving membrane permeability.
• Metabolic stability: Adamantane is resistant to oxidative metabolism, which can prolong the half-life of drug candidates.
• Metal complexation: The carboxylic acid and amide groups can coordinate with metal ions, useful in catalysis and materials science.
• Peptidomimetic scaffold: ACA can be incorporated into peptide chains to induce conformational constraints.

Source & Standardization

• Source: Synthetic, derived from L-proline and 1-adamantanecarboxylic acid derivatives.
• Manufacturing: Acylation reaction followed by crystallization and drying.
• Standardization: ≥98.0% (HPLC), with strict control of impurities and residual solvents.
• Forms: White to off-white crystalline powder.
• Applications: Pharmaceutical intermediates, chiral catalysts, research chemicals.

Specifications

Documentation & Supply

• Monthly capacity: 100 kg
• Lead time: 3-5 business days (stock items)
• Documentation: COA, MSDS, TDS available upon request
• Packaging: 25 kg fiber drum with double polyethylene liners, or customized packaging for small quantities

Request For Quote

• LyvBio Co., Ltd. — Email: info@lyvbio.com