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5-Bromo-N-Fmoc-L-tryptophan is a chemical compound that features a bromine atom attached to the 5th carbon of a tryptophan molecule, which is then modified with a fluorine-protected formyl-methyl group (Fmoc) at the nitrogen atom. This modification enhances its utility in various chemical and biological applications, making it a versatile component in organic synthesis, peptide chemistry, and drug discovery.

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  • 460751-66-0 Structure
  • Basic information

    1. Product Name: 5-Bromo-N-Fmoc-L-tryptophan
    2. Synonyms: 5-Bromo-N-Fmoc-L-tryptophan;(9H-Fluoren-9-yl)MethOxy]Carbonyl L-Trp(5-Br)-OH;(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(5-bromo-1H-indol-3-yl)propanoic acid;Fmoc-L-5-BromoTryptophan
    3. CAS NO:460751-66-0
    4. Molecular Formula: C26H21BrN2O4
    5. Molecular Weight: 505.35994
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 460751-66-0.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: 5-Bromo-N-Fmoc-L-tryptophan(CAS DataBase Reference)
    10. NIST Chemistry Reference: 5-Bromo-N-Fmoc-L-tryptophan(460751-66-0)
    11. EPA Substance Registry System: 5-Bromo-N-Fmoc-L-tryptophan(460751-66-0)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 460751-66-0(Hazardous Substances Data)

460751-66-0 Usage

Uses

Used in Organic Synthesis:
5-Bromo-N-Fmoc-L-tryptophan is used as a building block for the preparation of complex peptides and proteins. Its unique structure allows for the creation of a wide range of biologically active molecules, facilitating the development of new pharmaceuticals and therapeutic agents.
Used in Peptide Chemistry:
In peptide chemistry, 5-Bromo-N-Fmoc-L-tryptophan is utilized as a key component in the synthesis of peptides with specific functions. The bromine and Fmoc groups alter the chemical and biological properties of the tryptophan, enabling the design of peptides with tailored characteristics for various applications.
Used in Research:
5-Bromo-N-Fmoc-L-tryptophan is employed as a research tool in academic and industrial laboratories. Its unique properties make it valuable for studying the structure, function, and interactions of peptides and proteins, contributing to a deeper understanding of biological processes and the development of novel therapeutic strategies.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 5-Bromo-N-Fmoc-L-tryptophan is used for the development of new drug candidates and bioactive molecules. The introduction of bromine and Fmoc groups to the tryptophan molecule can enhance its pharmacological properties, making it a promising starting material for the creation of innovative medications.
Used in Drug Discovery and Development:
5-Bromo-N-Fmoc-L-tryptophan is a valuable tool in drug discovery and development, as its modified structure can be used to probe the activity of potential drug targets and identify lead compounds. Its unique chemical and biological properties make it an essential component in the search for new therapeutic agents to treat various diseases and conditions.

Check Digit Verification of cas no

The CAS Registry Mumber 460751-66-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 4,6,0,7,5 and 1 respectively; the second part has 2 digits, 6 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 460751-66:
(8*4)+(7*6)+(6*0)+(5*7)+(4*5)+(3*1)+(2*6)+(1*6)=150
150 % 10 = 0
So 460751-66-0 is a valid CAS Registry Number.

460751-66-0Downstream Products

460751-66-0Relevant articles and documents

Bromotryptophans and their incorporation in cyclic and bicyclic privileged peptides

García-Pindado, Júlia,Willemse, Tom,Goss, Rebecca,Maes, Bert U. W.,Giralt, Ernest,Ballet, Steven,Teixidó, Meritxell

, (2018/03/21)

While revisiting biologically active natural peptides, the importance of the tryptophan residue became clear. In this article, the incorporation of this amino acid, brominated at different positions of the indole ring, into cyclic peptides was successfully achieved. These products demonstrated improved properties in terms of passive diffusion, permeability across membranes, biostability in human serum and cytotoxicity. Moreover, these brominated tryptophans at positions 5, 6, or 7 proved to be compatible as building blocks to prepare bicyclic stapled peptides by performing on-resin Suzuki-Miyaura cross-coupling reactions.

A facile approach to tryptophan derivatives for the total synthesis of argyrin analogues

Chen, Chou-Hsiung,Genapathy, Sivaneswary,Fischer, Peter M.,Chan, Weng C.

, p. 9764 - 9768 (2015/01/09)

A facile route has been established for the synthesis of indole-substituted (S)-tryptophans from corresponding indoles, which utilizes a chiral auxiliary-facilitated Strecker amino acid synthesis strategy. The chiral auxiliary reagents evaluated were (S)-methylbenzylamine and related derivatives. To illustrate the robustness of the method, eight optically pure (S)-tryptophan analogues were synthesized, which were subsequently used for the convergent synthesis of a potent antibacterial agent, argyrin A and its analogues.

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