Cas no 21881-18-5 (Z-Phe-Ala-OH)

Z-Phe-Ala-OH is a protected dipeptide consisting of L-phenylalanine and L-alanine, with the N-terminus protected by a benzyloxycarbonyl (Z) group. This compound is commonly utilized in peptide synthesis as a building block, offering controlled coupling reactions due to its orthogonal protecting group. The Z-group enhances stability during solid-phase or solution-phase synthesis, minimizing unwanted side reactions. Its crystalline form ensures consistent purity and handling, making it suitable for research and pharmaceutical applications. The dipeptide’s structure allows for selective deprotection, facilitating further elongation or modification of peptide chains. Z-Phe-Ala-OH is valued for its reliability in producing well-defined intermediates in complex peptide assembly.
Z-Phe-Ala-OH structure
Z-Phe-Ala-OH structure
Product Name:Z-Phe-Ala-OH
CAS No:21881-18-5
MF:C20H22N2O5
MW:370.399085521698
MDL:MFCD00037237
CID:254462
Update Time:2025-07-01

Z-Phe-Ala-OH Chemical and Physical Properties

Names and Identifiers

    • L-Alanine,N-[(phenylmethoxy)carbonyl]-L-phenylalanyl-
    • Z-Phe-Ala-OH
    • (S)-2-((S)-2-(((Benzyloxy)carbonyl)amino)-3-phenylpropanamido)propanoic acid
    • Z-Phe-Ala
    • carbobenzyloxy-L-phenylalanyl-L-alanine
    • CBZ-L-PHE-ALA
    • CBZ-L-PHE-L-ALA
    • Cbz-L-Phe-L-Ala-OH
    • N-CARBOBENZOXY-L-PHENYLALANYL-L-ALANINE
    • N-carbobenzyloxy-Phe-Ala
    • N-CBZ-PHE-ALA
    • N-Cbz-Phe-Ala,Z-L-phenylalanyl-L-alanine
    • N-Cbz-Phe-Ala-OH
    • Z-L-PHENYLALANYL-L-ALANINE
    • Z-Phe-L-Ala
    • N-Benzyloxycarbonylphenylalanylalanine
    • L-Alanine, N-[(phenylmethoxy)carbonyl]-L-phenylalanyl-
    • Cbz-Phe-Ala-OH
    • Z-Phe-Ala-H
    • Z-L-Phe-L-Ala-OH
    • N(alpha)-Benzyloxycarbonyl-D-phenylalanyl-L-alanine
    • N-Cbz-L-phenylalanyl-L-alanine
    • N-carbobenzoxyphenylalanyl-alanine
    • LEJTXQOVOPDGHS-YOEHRIQ
    • MDL: MFCD00037237
    • Inchi: 1S/C20H22N2O5/c1-14(19(24)25)21-18(23)17(12-15-8-4-2-5-9-15)22-20(26)27-13-16-10-6-3-7-11-16/h2-11,14,17H,12-13H2,1H3,(H,21,23)(H,22,26)(H,24,25)/t14-,17-/m0/s1
    • InChI Key: LEJTXQOVOPDGHS-YOEHRIQHSA-N
    • SMILES: O=C([C@H](CC1C=CC=CC=1)NC(=O)OCC1C=CC=CC=1)N[C@H](C(=O)O)C

Computed Properties

  • Exact Mass: 370.15300
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 27
  • Rotatable Bond Count: 9
  • Complexity: 499
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: 4
  • XLogP3: 1.8
  • Topological Polar Surface Area: 105

Experimental Properties

  • Color/Form: {"from":"zh","to":"en","trans_result":[{"src":"\u672a\u786e\u5b9a","dst":"Not determined"},{"src":"2.\u00a0\u5bc6\u5ea6\uff08g\/mL,25\/4\u2103\uff09","dst":"2. density (g\/ml, 25\/4 \u2103)"}]}
  • Melting Point: 151-154?°C
  • PSA: 104.73000
  • LogP: 2.89520

Z-Phe-Ala-OH Security Information

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Z-Phe-Ala-OH Related Literature

Additional information on Z-Phe-Ala-OH

Professional Introduction to Compound with CAS No. 21881-18-5 and Product Name Z-Phe-Ala-OH

Compound with CAS No. 21881-18-5, chemically known as Z-Phe-Ala-OH, is a synthetic peptide derivative that has garnered significant attention in the field of biochemical research and pharmaceutical development. This compound, featuring a sequence of phenylalanyl-alanine with an azide protecting group at the N-terminus, serves as a crucial intermediate in the synthesis of more complex peptide-based therapeutics. The utility of Z-Phe-Ala-OH extends across multiple domains, including its role in the development of novel bioactive molecules and its application in structural biology studies.

The structural integrity and reactivity of Z-Phe-Ala-OH are underpinned by its well-defined chemical properties. The presence of the carbobenzyloxy (Z) group at the N-terminal amine provides stability during synthetic procedures, allowing for selective deprotection under mild acidic conditions. This characteristic makes it an invaluable building block for constructing larger peptides, particularly in cases where controlled cleavage is required to achieve the desired sequence without side reactions. The hydroxyl group at the C-terminus further enhances its versatility, enabling participation in various chemical transformations such as esterification or amidation.

In recent years, advancements in peptide chemistry have led to innovative applications of Z-Phe-Ala-OH. One notable area is its use in the design of peptidomimetics—molecules that mimic the structure and function of natural peptides but with improved pharmacokinetic properties. For instance, researchers have leveraged derivatives of Z-Phe-Ala-OH to develop small-molecule inhibitors targeting protein-protein interactions, which are challenging to address with traditional small-molecule drugs. These peptidomimetics often exhibit higher specificity and reduced immunogenicity compared to their peptide counterparts.

The role of Z-Phe-Ala-OH in drug discovery has been further highlighted by its incorporation into therapeutic candidates for various diseases. Studies have demonstrated its potential in modulating biological pathways associated with inflammation, cancer, and neurodegenerative disorders. For example, modified versions of this peptide have been investigated for their ability to interfere with inflammatory cytokine signaling by binding to specific receptors or enzymes. Such findings underscore the importance of Z-Phe-Ala-OH as a scaffold for developing next-generation biologics.

From a structural biology perspective, Z-Phe-Ala-OH has been instrumental in elucidating the three-dimensional structures of peptide-based proteins. Its well-defined conformational properties make it an excellent candidate for NMR spectroscopy and X-ray crystallography studies, providing critical insights into protein-peptide interactions. These structural insights are pivotal for rational drug design, enabling scientists to optimize peptides for enhanced binding affinity and therapeutic efficacy.

The synthesis of Z-Phe-Ala-OH itself is a testament to the progress in solid-phase peptide synthesis (SPPS) techniques. Modern SPPS methodologies allow for high-yield production of complex peptides with minimal purification steps, making compounds like Z-Phe-Ala-OH more accessible for research purposes. This accessibility has spurred numerous studies exploring novel applications and derivatives thereof, further expanding its utility in pharmaceutical and biotechnological fields.

Looking ahead, the future prospects for Z-Phe-Ala-OH appear promising as researchers continue to uncover new applications and refine synthetic methodologies. The integration of computational chemistry and machine learning algorithms has also accelerated the discovery process by predicting optimal modifications and predicting potential biological activities. Such innovations are expected to drive further advancements in peptide-based therapeutics derived from intermediates like Z-Phe-Ala-OH.

In conclusion, compound with CAS No. 21881-18-5, known as Z-Phe-Ala-OH, represents a cornerstone in modern peptide chemistry. Its versatility as a synthetic intermediate has enabled groundbreaking research across multiple disciplines, from drug discovery to structural biology. As scientific understanding evolves and new technologies emerge, the significance of this compound is poised to grow even further, solidifying its place as a vital tool in advancing biomedical research and therapeutic development.

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