Cas no 86060-99-3 (Fmoc-Asn-Opfp)

Fmoc-Asn-Opfp (Nα-Fmoc-Nβ-OPfp-L-asparagine) is a protected amino acid derivative widely used in solid-phase peptide synthesis (SPPS). The Fmoc (9-fluorenylmethoxycarbonyl) group provides orthogonal protection for the α-amino group, while the OPfp (pentafluorophenyl) ester activates the carboxyl group for efficient coupling with amines. This compound is particularly valued for its high reactivity and selectivity, minimizing side reactions during peptide chain elongation. Its crystalline form ensures stability and ease of handling. Fmoc-Asn-Opfp is especially useful in synthesizing complex peptides, offering reliable performance in automated and manual synthesis protocols. The pentafluorophenyl ester also enhances solubility in organic solvents, facilitating homogeneous reaction conditions.
Fmoc-Asn-Opfp structure
Fmoc-Asn-Opfp structure
Product Name:Fmoc-Asn-Opfp
CAS No:86060-99-3
MF:C25H17F5N2O5
MW:520.404904127121
MDL:MFCD00065625
CID:720777
PubChem ID:24871005
Update Time:2025-05-21

Fmoc-Asn-Opfp Chemical and Physical Properties

Names and Identifiers

    • L-Asparagine,N<sup>2</sup>-[(9H-fluoren-9-ylmethoxy)carbonyl]-, 2,3,4,5,6-pentafluorophenyl ester
    • Fmoc-Asn-OPfp
    • (2,3,4,5,6-pentafluorophenyl) (2S)-4-amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxobutanoate
    • Fmoc-Asn-pentafluorophenyl ester
    • Fmoc-L-asparagine pentafluorophenyl ester
    • U999
    • L-Asparagine, N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-, pentafluorophenyl ester (9CI)
    • N2-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-asparagine 2,3,4,5,6-pentafluorophenyl ester (ACI)
    • N Alpha-fmoc-L-asparagine pentafluorophenyl ester
    • DTXSID60446662
    • AKOS015853405
    • MFCD00065625
    • 86060-99-3
    • FD21197
    • AKOS015902673
    • (S)-perfluorophenyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-amino-4-oxobutanoate
    • Fmoc-Asn-Opfp
    • MDL: MFCD00065625
    • Inchi: 1S/C25H17F5N2O5/c26-18-19(27)21(29)23(22(30)20(18)28)37-24(34)16(9-17(31)33)32-25(35)36-10-15-13-7-3-1-5-11(13)12-6-2-4-8-14(12)15/h1-8,15-16H,9-10H2,(H2,31,33)(H,32,35)/t16-/m0/s1
    • InChI Key: FESVUEALWMQZEP-INIZCTEOSA-N
    • SMILES: C(C1C2=CC=CC=C2C2C=CC=CC1=2)OC(=O)N[C@@H](CC(=O)N)C(=O)OC1C(F)=C(F)C(F)=C(F)C=1F

Computed Properties

  • Exact Mass: 520.10600
  • Monoisotopic Mass: 520.10576246g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 7
  • Heavy Atom Count: 37
  • Rotatable Bond Count: 10
  • Complexity: 814
  • 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: 3.9
  • Topological Polar Surface Area: 108?2

Experimental Properties

  • Color/Form: White powder
  • PSA: 107.72000
  • LogP: 5.16140
  • Solubility: Not determined

Fmoc-Asn-Opfp Security Information

  • WGK Germany:3

Fmoc-Asn-Opfp Pricemore >>

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Fmoc-Asn-Opfp Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: 4-Methylmorpholine ,  9-Fluorenylmethyl chloroformate ;  10 min, -15 °C
1.2 Solvents: Tetrahydrofuran ;  -15 °C → rt
Reference
9-Fluorenylmethyl chloroformate (Fmoc-Cl) as a useful reagent for the synthesis of pentafluorophenyl, 2,4,5-trichlorophenyl, pentachlorophenyl, p-nitrophenyl, o-nitrophenyl and succinimidyl esters of Nα-urethane protected amino acids
Tantry, Subramanyam J.; Babu, Vommina V. Suresh, Letters in Peptide Science, 2004, 10(5-6), 655-662

Production Method 2

Reaction Conditions
1.1 Solvents: 1,4-Dioxane
1.2 Solvents: Dimethylformamide
1.3 Reagents: 1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride
1.4 Solvents: Water
1.5 Solvents: 1,4-Dioxane
Reference
Preparation of N-9-fluorenylmethyloxycarbonyl-asparagine-pentafluorophenyl ester from the free acid
Gyi, Jeffrey I.; Kinsman, Richard G.; Rees, Anthony R., Synlett, 1995, (2), 205-6

Fmoc-Asn-Opfp Raw materials

Fmoc-Asn-Opfp Preparation Products

Fmoc-Asn-Opfp Suppliers

Amadis Chemical Company Limited
Gold Member
Audited Supplier Audited Supplier
(CAS:86060-99-3)Fmoc-Asn-Opfp
Order Number:A863322
Stock Status:in Stock
Quantity:25g
Purity:99%
Pricing Information Last Updated:Friday, 30 August 2024 08:40
Price ($):508.0

Additional information on Fmoc-Asn-Opfp

Fmoc-Asn-Opfp: A Comprehensive Overview

Fmoc-Asn-Opfp, also known by its CAS number 86060-99-3, is a specialized chemical compound widely utilized in the field of peptide synthesis. This compound is a derivative of asparagine, a naturally occurring amino acid, and is commonly employed as a protecting group in solid-phase peptide synthesis (SPPS). The full name of this compound is 9-fluorenylmethyloxycarbonyl-N-(2,3,5,6-tetrafluorophenyl)asparagine, which highlights its structural composition and functional groups.

The development and application of Fmoc-Asn-Opfp have significantly contributed to advancements in peptide chemistry. Its structure incorporates the Fmoc (9-fluorenylmethyloxycarbonyl) group, which serves as a protecting group for the amine terminus of amino acids during peptide synthesis. The Opfp (2,3,5,6-tetrafluorophenyl) group further enhances the stability and reactivity of the compound in synthetic reactions. This combination makes Fmoc-Asn-Opfp an invaluable tool in modern peptide synthesis.

Recent studies have demonstrated the versatility of Fmoc-based protecting groups in various chemical reactions. For instance, researchers have explored the use of Fmoc-Asn-Opfp in the synthesis of bioactive peptides with complex structures. These peptides are being investigated for their potential applications in drug discovery and therapeutic development. The ability to precisely control the synthesis process using compounds like Fmoc-Asn-Opfp has enabled scientists to create peptides with enhanced stability and bioavailability.

In addition to its role in peptide synthesis, Fmoc-Asn-Opfp has found applications in other areas of organic chemistry. For example, it has been used as a building block in the construction of larger biomolecules and as an intermediate in the synthesis of complex natural products. The unique properties of this compound make it a valuable asset in both academic research and industrial settings.

The synthesis of Fmoc-Asn-Opfp involves a series of well-established chemical reactions. The process typically begins with the preparation of the Fmoc group, followed by its coupling with asparagine derivatives. The introduction of the Opfp group requires careful optimization to ensure high yields and product purity. Recent advancements in catalytic methods and reaction conditions have further improved the efficiency of these synthetic steps.

The use of Fmoc-based reagents like Fmoc-Asn-Opfp has also been explored in green chemistry initiatives. Researchers are increasingly focusing on developing environmentally friendly methods for peptide synthesis that minimize waste and reduce energy consumption. The compatibility of Fmoc-based reagents with such methods makes them attractive candidates for sustainable chemical processes.

In conclusion, CAS No. 86060-99-3 (Fmoc-Asn-OFPF) strong> stands as a testament to the ingenuity and precision required in modern chemical synthesis. Its role in peptide chemistry continues to expand as researchers uncover new applications and optimize existing synthetic strategies. As science advances, compounds like this will remain at the forefront of innovation, driving progress across diverse fields such as medicine, biotechnology, and materials science.

Recommended suppliers
Amadis Chemical Company Limited
(CAS:86060-99-3)Fmoc-Asn-Opfp
A863322
Purity:99%
Quantity:25g
Price ($):508.0
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