Cas no 56762-93-7 (Z-L-Methionine methyl ester)

Z-L-Methionine methyl ester is a protected derivative of L-methionine, commonly used in peptide synthesis and biochemical research. The Z (benzyloxycarbonyl) group serves as a protective moiety for the amino functionality, while the methyl ester protects the carboxyl group, enhancing stability during synthetic procedures. This compound is particularly valuable in solid-phase peptide synthesis (SPPS) and other applications requiring selective deprotection strategies. Its high purity and well-defined reactivity profile make it a reliable building block for constructing complex peptides. The methyl ester group also facilitates solubility in organic solvents, simplifying handling and purification processes. Suitable for use in both academic and industrial settings, it ensures consistent performance in demanding synthetic workflows.
Z-L-Methionine methyl ester structure
Z-L-Methionine methyl ester structure
Product Name:Z-L-Methionine methyl ester
CAS No:56762-93-7
MF:C14H19NO4S
MW:297.369962930679
MDL:MFCD00145551
CID:365969
PubChem ID:11141035
Update Time:2025-08-05

Z-L-Methionine methyl ester Chemical and Physical Properties

Names and Identifiers

    • (S)-Methyl 2-(((benzyloxy)carbonyl)amino)-4-(methylthio)butanoate
    • L-Methionine, N-[(phenylmethoxy)carbonyl]-, methyl ester
    • methyl (2S)-4-methylsulfanyl-2-(phenylmethoxycarbonylamino)butanoate
    • Z-L-METHIONINE METHYL ESTER
    • Z-MET-OME
    • Cbz-L-methionine methyl ester
    • N-benzyloxycarbonyl-L-methionine methyl ester
    • N-Benzyloxycarbonyl-L-methionin-methylester
    • (S)-2-[(Benzyloxycarbonyl)amino]-4-methylsulfanylbutanoic acid methyl ester
    • L-Cbz methionine methyl ester
    • Cbz-L-methioninemethylester
    • (S)-methyl 2-(benzyloxycarbonylamino)-4-(methylthio)butanoate
    • N-(Benzyloxycarbonyl)-L-methionine methyl ester
    • YGDBSBBHEWHVAJ-LBPRGKRZSA-N
    • KM0029
    • FCH3613011
    • AB0058042
    • ST51016
    • methyl (2S)-2-{[(benzyloxy)carbonyl]amino}-4-(methylsulfanyl)butanoate
    • F10941
    • A869852
    • 56762-93-7
    • (S)-Methyl2-(((benzyloxy)carbonyl)amino)-4-(methylthio)butanoate
    • Z-L-Met-OMe
    • CS-0204525
    • Methyl ((benzyloxy)carbonyl)-L-methioninate
    • DTXSID90456734
    • MFCD00145551
    • Z-Met-OMe, >=99.0% (sum of enantiomers, HPLC)
    • SCHEMBL4731152
    • FS-4101
    • (S)-2-Benzyloxycarbonylamino-4-methylsulfanyl-butyric acid methyl ester
    • 83972-33-2
    • AKOS015850853
    • AMY22203
    • DB-007347
    • Z-L-Methionine methyl ester
    • MDL: MFCD00145551
    • Inchi: 1S/C14H19NO4S/c1-18-13(16)12(8-9-20-2)15-14(17)19-10-11-6-4-3-5-7-11/h3-7,12H,8-10H2,1-2H3,(H,15,17)/t12-/m0/s1
    • InChI Key: YGDBSBBHEWHVAJ-LBPRGKRZSA-N
    • SMILES: S(C)CC[C@@H](C(=O)OC)NC(=O)OCC1C=CC=CC=1

Computed Properties

  • Exact Mass: 297.10300
  • Monoisotopic Mass: 297.10347926g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 20
  • Rotatable Bond Count: 9
  • Complexity: 306
  • 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
  • Topological Polar Surface Area: 89.9
  • XLogP3: 2.4

Experimental Properties

  • Density: 1.182±0.06 g/cm3 (20 oC 760 Torr),
  • Melting Point: 41-44?°C
  • Solubility: Very slightly soluble (0.57 g/l) (25 o C),
  • PSA: 89.93000
  • LogP: 2.59840

Z-L-Methionine methyl ester Security Information

Z-L-Methionine methyl ester Customs Data

  • HS CODE:2930909090
  • Customs Data:

    China Customs Code:

    2930909090

    Overview:

    2930909090. Other organic sulfur compounds. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:30.0%

    Declaration elements:

    Product Name, component content, use to

    Summary:

    2930909090. other organo-sulphur compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

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Z-L-Methionine methyl ester Production Method

Additional information on Z-L-Methionine methyl ester

Introduction to Z-L-Methionine Methyl Ester (CAS No. 56762-93-7) and Its Recent Applications in Chemical Biology and Medicine

The compound Z-L-Methionine Methyl Ester, identified by the Chemical Abstracts Service registry number 56762-93-7, represents a significant advancement in the field of peptidomimetics and protease inhibition. As a derivative of the essential amino acid methionine, this compound has garnered considerable attention due to its unique structural and functional properties, which make it a valuable tool in both academic research and pharmaceutical development.

Z-L-Methionine Methyl Ester is synthesized through a meticulous process that involves the protection of the methionine side chain, followed by esterification to enhance its stability and solubility. This modification not only preserves the bioactive residues of methionine but also introduces additional functionalities that allow for selective interactions with biological targets. The ester group, in particular, plays a crucial role in modulating the compound's reactivity and binding affinity, making it an ideal candidate for designing novel therapeutic agents.

In recent years, the applications of Z-L-Methionine Methyl Ester have expanded significantly, particularly in the realm of protease inhibition. Proteases are enzymes that play pivotal roles in various physiological processes, including signal transduction, protein degradation, and blood clotting. Dysregulation of protease activity is associated with numerous diseases, such as cancer, inflammation, and neurodegenerative disorders. By developing protease inhibitors based on Z-L-Methionine Methyl Ester, researchers have been able to create highly specific and potent drugs that target these enzymes with minimal off-target effects.

One of the most notable recent advancements involves the use of Z-L-Methionine Methyl Ester in the development of targeted cancer therapies. Cancer cells often exhibit aberrant protease activity, which contributes to their invasive and metastatic properties. By inhibiting key proteases such as matrix metalloproteinases (MMPs) and cathepsins, researchers have been able to slow down tumor progression and enhance the efficacy of existing treatments. For instance, studies have shown that Z-L-Methionine Methyl Ester derivatives can effectively inhibit MMP-9, a protease known to be involved in tumor invasion and angiogenesis. This has opened up new avenues for developing combination therapies that synergize with traditional chemotherapeutic agents.

The compound's utility extends beyond cancer therapy; it has also been explored in treating inflammatory diseases. Inflammatory processes are mediated by a complex interplay of proteases and their inhibitors, often leading to chronic inflammation if not properly regulated. Z-L-Methionine Methyl Ester has been shown to modulate inflammatory pathways by inhibiting key enzymes such as caspase-1 and interleukin-1β converting enzyme (ICE). By doing so, it can help reduce inflammation without compromising host defense mechanisms, making it a promising candidate for conditions like rheumatoid arthritis and inflammatory bowel disease.

Another exciting application of Z-L-Methionine Methyl Ester is in the field of neuroscience. Neurodegenerative diseases such as Alzheimer's disease and Parkinson's disease are characterized by the accumulation of misfolded proteins that form toxic aggregates. These aggregates are often cleared by proteolytic mechanisms that become impaired in affected individuals. Research has demonstrated that Z-L-Methionine Methyl Ester can enhance proteasome activity, thereby promoting the degradation of these toxic protein species. This has led to significant improvements in animal models of neurodegenerative diseases, suggesting potential therapeutic benefits for patients.

The synthesis and optimization of Z-L-Methionine Methyl Ester derivatives have also contributed to advancements in peptidomimetic chemistry. Peptidomimetics are designed to mimic the bioactivity of natural peptides while offering improved pharmacokinetic properties such as enhanced stability and oral bioavailability. The methionine residue is particularly important in peptide design due to its role as a nucleation site for β-turn formation, which is crucial for maintaining peptide conformational flexibility. By incorporating Z-L-Methionine Methyl Ester into peptidomimetic scaffolds, researchers can fine-tune both structure and function to achieve desired biological outcomes.

Recent studies have also highlighted the role of Z-L-Methionine Methyl Ester in drug delivery systems. Nanotechnology-based delivery platforms have emerged as powerful tools for enhancing drug efficacy by improving targeting specificity and reducing systemic toxicity. By conjugating Z-L-Methionine Methyl Ester derivatives to nanoparticles or liposomes, researchers have been able to develop targeted drug delivery systems that selectively accumulate at sites of disease activity. This approach has shown promise in delivering both small molecule inhibitors and biologics with improved therapeutic profiles.

The future prospects for Z-L-Methionine Methyl Ester are vast and multifaceted. As our understanding of biological processes continues to evolve, new applications for this compound are likely to emerge. Advances in computational chemistry and artificial intelligence are also expected to accelerate the design and optimization of novel derivatives with enhanced biological activity. Additionally, interdisciplinary collaborations between chemists, biologists, and clinicians will be crucial in translating laboratory findings into effective clinical therapies.

In conclusion,Z-L-Methionine Methyl Ester (CAS No. 56762-93-7) represents a cornerstone compound in modern chemical biology and medicine. Its unique structural features enable its use as a versatile tool for developing targeted therapies across various disease areas including cancer, inflammation, and neurodegenerative disorders. As research continues to uncover new applications for this compound,Z-L-Methionine Methyl Ester is poised to play an increasingly important role in shaping the future of drug discovery and development.

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