Cas no 86060-83-5 (Fmoc-Asp-OBzl)

Fmoc-Asp-OBzl (Fmoc-L-aspartic acid β-benzyl ester) is a protected derivative of aspartic acid, widely used in solid-phase peptide synthesis (SPPS). The Fmoc (9-fluorenylmethoxycarbonyl) group provides orthogonal protection for the α-amino group, enabling selective deprotection under mild basic conditions, while the benzyl (Bzl) ester safeguards the β-carboxyl group against premature activation. This compound is particularly valuable for introducing aspartic acid residues into peptide chains with precise control, minimizing side reactions. Its stability under SPPS conditions and compatibility with standard Fmoc-chemistry protocols make it a reliable choice for researchers. The product is typically characterized by high purity, ensuring consistent performance in complex peptide assembly.
Fmoc-Asp-OBzl structure
Fmoc-Asp-OBzl structure
Product Name:Fmoc-Asp-OBzl
CAS No:86060-83-5
MF:C26H23NO6
MW:445.463927507401
MDL:MFCD00198201
CID:60939
PubChem ID:11224591
Update Time:2025-08-02

Fmoc-Asp-OBzl Chemical and Physical Properties

Names and Identifiers

    • Fmoc-Asp-OBzl
    • (3S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxo-4-phenylmethoxybutanoic acid
    • (S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-(benzyloxy)-4-oxobutanoic acid
    • Fmoc-L-Asparticacid-1-benzylester
    • FMOC-L-ASP-OBZL
    • N-9-FLUORENYLMETHYLOXYCARBONYL-L-ASPARTIC ACID 1-BENZYL ESTER
    • Fmoc-Asp(Obzl)-OH
    • 1-benzyl N-fluoren-9-ylmethoxycarbonyl-L-aspartate
    • A-benzyl ester
    • benzyl N-(9-fluorenylmethoxycarbonyl)-L-aspartic acid
    • Fmoc-L-Aspartic
    • Fmoc-L-Aspartic acid a-benzyl ester
    • Fmoc-L-Aspartic acid-1-benzyl ester
    • Fmoc-L-aspartic acid alpha-benzyl ester
    • N-Fmoc-L-aspartic Acid 1-Benzyl Ester
    • PubChem14955
    • Fmoc-asp-obzl, AldrichCPR
    • CBZSVHFNEMONDZ-QHCPKHFHSA-N
    • FCH3661525
    • AM81639
    • VA50287
    • CS-W0
    • 1-(Phenylmethyl) hydrogen N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-aspartate (ACI)
    • (3S)-4-(benzyloxy)-3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-4-oxobutanoic acid
    • HY-W008360
    • 86060-83-5
    • SCHEMBL6588912
    • (S)-3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(benzyloxy)-4-oxobutanoic acid
    • AC-30253
    • MFCD00198201
    • AKOS015888153
    • CS-W008360
    • DTXSID30459300
    • (3S)-4-(BENZYLOXY)-3-{[(9H-FLUOREN-9-YLMETHOXY)CARBONYL]AMINO}-4-OXOBUTANOIC ACID
    • EN300-7388578
    • AS-17270
    • AC1168
    • N-alpha-(9-Fluorenylmethyloxycarbonyl)-L-aspartic acid alpha-benzyl ester
    • AKOS015922801
    • MDL: MFCD00198201
    • Inchi: 1S/C26H23NO6/c28-24(29)14-23(25(30)32-15-17-8-2-1-3-9-17)27-26(31)33-16-22-20-12-6-4-10-18(20)19-11-5-7-13-21(19)22/h1-13,22-23H,14-16H2,(H,27,31)(H,28,29)/t23-/m0/s1
    • InChI Key: CBZSVHFNEMONDZ-QHCPKHFHSA-N
    • SMILES: C(C1C2=CC=CC=C2C2C=CC=CC1=2)OC(=O)N[C@@H](CC(=O)O)C(=O)OCC1C=CC=CC=1

Computed Properties

  • Exact Mass: 445.15300
  • Monoisotopic Mass: 445.15253745g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 6
  • Heavy Atom Count: 33
  • Rotatable Bond Count: 10
  • Complexity: 668
  • 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: 102
  • Surface Charge: 0
  • Tautomer Count: 2
  • XLogP3: 4

Experimental Properties

  • Color/Form: No data available
  • Density: 1.3100
  • Melting Point: 118-122°C
  • Boiling Point: 683.7°C at 760 mmHg
  • Flash Point: 367.3±31.5 °C
  • Refractive Index: 1.62
  • PSA: 101.93000
  • LogP: 4.50270
  • Specific Rotation: -19.4° (c=1, DMF)

Fmoc-Asp-OBzl Security Information

Fmoc-Asp-OBzl Pricemore >>

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Fmoc-Asp-OBzl Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Formic acid Solvents: Dichloromethane ;  overnight, rt
Reference
Synthesis of constrained tetracyclic peptides by consecutive CEPS, CLIPS, and oxime ligation
Streefkerk, Dieuwertje E.; Schmidt, Marcel ; Ippel, Johannes H.; Hackeng, Tilman M.; Nuijens, Timo; et al, Organic Letters, 2019, 21(7), 2095-2100

Production Method 2

Reaction Conditions
1.1 Reagents: Trifluoroacetic acid Solvents: Dichloromethane ;  30 min, rt
Reference
Synthesis and assay of retro-α4β1 integrin-targeting motifs
Dattoli, Samantha D.; De Marco, Rossella; Baiula, Monica; Spampinato, Santi; Greco, Arianna; et al, European Journal of Medicinal Chemistry, 2014, 73, 225-232

Production Method 3

Reaction Conditions
1.1 Reagents: Trifluoroacetic acid Solvents: Dichloromethane ;  15 min, rt
Reference
5-aminomethyloxazolidine-2,4-dione hybrid α/β-dipeptide scaffolds as inductors of constrained conformations: Applications to the synthesis of integrin antagonists
De Marco, Rossella; Mazzotti, Giacomo; Dattoli, Samantha D.; Baiula, Monica; Spampinato, Santi; et al, Biopolymers, 2015, 104(5), 636-649

Production Method 4

Reaction Conditions
1.1 Reagents: Trifluoroacetic acid ,  Anisole
Reference
Amino sugars. 135. The preparation of a partially protected heptasaccharide-asparagine intermediate for glycopeptide synthesis
Nakabayashi, Satoru; Warren, Christopher D.; Jeanloz, Roger W., Carbohydrate Research, 1988, 174, 279-89

Fmoc-Asp-OBzl Raw materials

Fmoc-Asp-OBzl Preparation Products

Additional information on Fmoc-Asp-OBzl

Fmoc-Asp-OBzl: A Comprehensive Overview

The compound with CAS number 86060-83-5, commonly referred to as Fmoc-Asp-OBzl, is a critical reagent in the field of peptide synthesis. This compound is a protected form of aspartic acid, where the amino group is protected by a fluorenylmethyloxycarbonyl (Fmoc) group, and the carboxylic acid is protected as a benzyl ester (OBzl). The Fmoc protecting group is widely used in solid-phase peptide synthesis (SPPS) due to its stability under basic conditions and ease of removal under acidic conditions. Similarly, the benzyl ester (OBzl) group provides excellent protection for the carboxylic acid during the synthesis process.

Recent advancements in peptide chemistry have highlighted the importance of Fmoc-Asp-OBzl in the construction of complex peptide sequences. Researchers have demonstrated that the use of this reagent significantly improves the efficiency and yield of peptide synthesis, particularly in the construction of bioactive peptides and therapeutic agents. For instance, studies published in *Journal of Peptide Science* have shown that Fmoc-Asp-OBzl plays a pivotal role in the synthesis of cyclic peptides, which are known for their potent bioactivity and drug-like properties.

The structural integrity of Fmoc-Asp-OBzl is crucial for its performance in peptide synthesis. The Fmoc group ensures that the amino terminus remains unreactive during coupling reactions, while the OBzl group protects the carboxyl terminus from unwanted side reactions. This dual protection system allows for precise control over the synthesis process, enabling chemists to construct peptides with high fidelity and complexity. Moreover, the ease of removal of both protecting groups under mild acidic conditions makes Fmoc-Asp-OBzl a versatile tool in modern peptide chemistry.

Recent research has also explored the application of Fmoc-Asp-OBzl in the synthesis of bioconjugates and modified peptides. For example, scientists at Stanford University have utilized this reagent to synthesize peptides with post-translational modifications, such as phosphorylation and glycosylation. These modified peptides are valuable tools for studying protein-protein interactions and enzyme kinetics. The ability to incorporate such modifications directly into synthetic peptides has opened new avenues for drug discovery and biotechnological applications.

In addition to its role in peptide synthesis, Fmoc-Asp-OBzl has been employed in the development of novel materials and nanotechnology applications. Researchers at MIT have reported on the use of this compound in the construction of self-assembling peptide nanofibers, which exhibit unique mechanical and electronic properties. These nanofibers have potential applications in tissue engineering, drug delivery systems, and electronic devices.

The demand for high-quality reagents like Fmoc-Asp-O B zl continues to grow as peptide-based therapeutics gain prominence in the pharmaceutical industry. Companies specializing in fine chemicals and reagents are increasingly focusing on optimizing production processes to meet this demand while maintaining high standards of purity and consistency. Innovations in manufacturing techniques, such as continuous-flow chemistry and automated purification systems, are expected to further enhance the availability and affordability of this compound.

In conclusion, Fmoc-O B zl stands as a testament to the ingenuity and precision required in modern chemical synthesis. Its role in advancing peptide research underscores its importance as a cornerstone reagent in contemporary chemistry. As research continues to uncover new applications for this compound, it is likely that Fmoc-O B zl will remain at the forefront of peptide science for years to come.

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