Cas no 1911-74-6 (L-Proline,1-(triphenylmethyl)-)

1-(Triphenylmethyl)-L-proline is a protected derivative of L-proline, where the nitrogen atom is shielded by a trityl (triphenylmethyl) group. This modification enhances the compound's stability and selectivity in peptide synthesis and other organic transformations. The trityl group serves as a robust protecting group, preventing unwanted side reactions while maintaining the stereochemical integrity of the proline moiety. This derivative is particularly useful in solid-phase peptide synthesis (SPPS) and asymmetric catalysis, where controlled deprotection is required. Its high purity and well-defined structure make it a reliable intermediate for researchers in medicinal chemistry and biochemistry. The compound is typically supplied as a white crystalline solid, ensuring consistent performance in synthetic applications.
L-Proline,1-(triphenylmethyl)- structure
1911-74-6 structure
Product Name:L-Proline,1-(triphenylmethyl)-
CAS No:1911-74-6
MF:C24H23NO2
MW:357.44492650032
CID:136184
PubChem ID:7317450
Update Time:2025-10-24

L-Proline,1-(triphenylmethyl)- Chemical and Physical Properties

Names and Identifiers

    • L-Proline,1-(triphenylmethyl)-
    • (2S)-1-tritylpyrrolidine-2-carboxylic acid
    • TRT-PRO-OH
    • (L)-Trt-Pro-OH
    • (S)-tritylproline
    • AC1OJB10
    • AG-E-39596
    • AM82204
    • CTK4E0607
    • KB-62174
    • N-Trityl-L-prolin
    • N-tritylproline
    • SureCN4629180
    • Trityl-L-Proline
    • DTXSID00428528
    • (S)-1-Tritylpyrrolidine-2-carboxylic acid
    • (S)-1-Tritylpyrrolidine-2-carboxylicacid
    • SCHEMBL4629180
    • 1911-74-6
    • Inchi: 1S/C24H23NO2/c26-23(27)22-17-10-18-25(22)24(19-11-4-1-5-12-19,20-13-6-2-7-14-20)21-15-8-3-9-16-21/h1-9,11-16,22H,10,17-18H2,(H,26,27)/t22-/m0/s1
    • InChI Key: BDFHBICZVAVNCD-QFIPXVFZSA-N
    • SMILES: OC([C@@H]1CCCN1C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=O

Computed Properties

  • Exact Mass: 357.172878976g/mol
  • Monoisotopic Mass: 357.172878976g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 27
  • Rotatable Bond Count: 5
  • Complexity: 441
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 2.8
  • Topological Polar Surface Area: 40.5?2

L-Proline,1-(triphenylmethyl)- Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
Alichem
A109005344-1g
(S)-1-Tritylpyrrolidine-2-carboxylic acid
1911-74-6 97%
1g
$474.70 2023-09-02

L-Proline,1-(triphenylmethyl)- Related Literature

Additional information on L-Proline,1-(triphenylmethyl)-

Professional Introduction to L-Proline,1-(triphenylmethyl)- and CAS No. 1911-74-6

L-Proline,1-(triphenylmethyl)-, identified by the chemical compound CAS No. 1911-74-6, is a significant derivative of the essential amino acid proline. This compound has garnered considerable attention in the field of pharmaceutical chemistry and bioorganic synthesis due to its unique structural properties and versatile applications. The presence of a triphenylmethyl group at the N-terminal position introduces enhanced stability and reactivity, making it a valuable intermediate in the synthesis of complex molecules.

The structural framework of L-Proline,1-(triphenylmethyl)- consists of a proline core substituted with a bulky triphenylmethyl moiety. This modification imparts distinct physicochemical characteristics, such as increased lipophilicity and reduced solubility in polar solvents. These properties are particularly advantageous in drug design, where precise control over molecular interactions is crucial for achieving optimal pharmacokinetic profiles.

Recent advancements in medicinal chemistry have highlighted the utility of L-Proline,1-(triphenylmethyl)- as a building block in the development of novel therapeutic agents. Its incorporation into peptide mimetics and protease inhibitors has demonstrated promising results in preclinical studies. For instance, derivatives of this compound have shown efficacy in modulating enzyme activity, which is critical for treating conditions such as inflammation and metabolic disorders.

The synthesis of L-Proline,1-(triphenylmethyl)- typically involves multi-step organic transformations, including nucleophilic substitution and ring-closure reactions. The use of high-purity starting materials and optimized reaction conditions is essential to ensure high yield and minimal byproduct formation. Modern synthetic methodologies, such as transition-metal-catalyzed cross-coupling reactions, have further refined the production process, enabling scalable manufacturing for industrial applications.

In the realm of bioorganic chemistry, L-Proline,1-(triphenylmethyl)- has been employed in the development of chiral auxiliaries and ligands for asymmetric synthesis. The rigid conformation imposed by the proline backbone combined with the steric bulk of the triphenylmethyl group facilitates selective binding interactions, enhancing enantioselectivity in catalytic processes. This has opened new avenues for producing enantiomerically pure compounds with high pharmaceutical relevance.

Biological studies have also explored the potential of L-Proline,1-(triphenylmethyl)- as a modulator of protein-protein interactions. Its ability to mimic natural amino acid sequences while introducing functional handles has led to innovative approaches in drug discovery. For example, peptidomimetics incorporating this moiety have demonstrated improved binding affinity to target proteins compared to their peptide counterparts, offering a strategic advantage in therapeutic development.

The role of CAS No. 1911-74-6 in material science cannot be overlooked either. Beyond its pharmaceutical applications, this compound serves as a valuable precursor in polymer chemistry and material engineering. Its incorporation into specialty polymers enhances mechanical strength and thermal stability, making it suitable for advanced materials used in electronics and coatings.

Future research directions for L-Proline,1-(triphenylmethyl)- are likely to focus on expanding its utility in drug delivery systems and nanotechnology. The development of smart drug formulations that leverage its structural features could lead to more targeted and efficient therapeutic interventions. Additionally, its potential as a component in biodegradable materials aligns with growing environmental concerns and sustainable chemistry initiatives.

In conclusion, L-Proline,1-(triphenylmethyl)-, identified by CAS No. 1911-74-6, represents a versatile compound with broad applications across pharmaceuticals, materials science, and bioorganic chemistry. Its unique structural attributes and functional adaptability continue to drive innovation in synthetic methodologies and biological research. As scientific understanding progresses, the significance of this compound is expected to grow further, solidifying its position as a cornerstone in modern chemical research.

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