Fmoc-L-aspartic acid a-9-fluorenylmethyl ester
Need Assistance?
  • US & Canada:
    +
  • UK: +

Fmoc-L-aspartic acid a-9-fluorenylmethyl ester

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Category
Fmoc-Amino Acids
Catalog number
BAT-003733
CAS number
187671-16-5
Molecular Formula
C33H27NO6
Molecular Weight
533.59
Fmoc-L-aspartic acid a-9-fluorenylmethyl ester
IUPAC Name
(3S)-4-(9H-fluoren-9-ylmethoxy)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxobutanoic acid
Synonyms
Fmoc-L-Asp-OFm; (3S)-4-(9H-fluoren-9-ylmethoxy)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxobutanoic acid; N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-aspartic acid 1-(9H-fluoren-9-ylmethyl) ester; fmoc-asp-ofm
Appearance
White powder
Purity
≥ 98% (HPLC)
Density
1.322 g/cm3
Melting Point
196-207 °C
Boiling Point
777.9 °C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C33H27NO6/c35-31(36)17-30(32(37)39-18-28-24-13-5-1-9-20(24)21-10-2-6-14-25(21)28)34-33(38)40-19-29-26-15-7-3-11-22(26)23-12-4-8-16-27(23)29/h1-16,28-30H,17-19H2,(H,34,38)(H,35,36)/t30-/m0/s1
InChI Key
AAVDDDPGTRDTJT-PMERELPUSA-N
Canonical SMILES
C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)C(CC(=O)O)NC(=O)OCC4C5=CC=CC=C5C6=CC=CC=C46

Fmoc-L-aspartic acid α-9-fluorenylmethyl ester, a pivotal reagent in peptide synthesis and biochemical research, presents a plethora of applications. Here are four key applications articulated with a high degree of perplexity and burstiness:

Peptide Synthesis: An indispensable tool in solid-phase peptide synthesis, Fmoc-L-aspartic acid α-9-fluorenylmethyl ester stands as a stalwart component renowned for its stability and effortless removal. It acts as a protective barrier for the amino acid aspartic acid, allowing for the incremental assembly of amino acids to form intricate peptides. This reagent ensures heightened purity and efficiency in crafting complex peptides, serving both research endeavors and therapeutic pursuits with unparalleled efficacy.

Protein Engineering: Within the domain of protein engineering, Fmoc-L-aspartic acid α-9-fluorenylmethyl ester assumes a pivotal role in embedding aspartic acid residues into synthetic proteins or protein fragments. This integration facilitates the exploration of protein function, structure, and interactions through the incorporation of customized amino acid sequences. Researchers can conceive and synthesize modified proteins imbued with desired traits for experimental and industrial applications.

Drug Development: Serving as a cornerstone in the synthesis of peptide-based drug candidates, Fmoc-L-aspartic acid α-9-fluorenylmethyl ester enables the production of peptides containing aspartic acid residues, known for their unique biological activities, such as receptor binding or enzyme inhibition. This reagent streamlines the generation of therapeutic peptides, which undergo rigorous evaluation for their potential in combating a spectrum of diseases.

Bioconjugation: In the realm of bioconjugation methodologies, Fmoc-L-aspartic acid α-9-fluorenylmethyl ester emerges as a valuable resource for conjugating peptides or small molecules with proteins, nucleic acids, or other biomolecules. This fusion is critical for designing targeted drug delivery systems, diagnostics, and imaging agents, enhancing the functionality and specificity of resulting bioconjugates. By enabling precise and robust conjugation, this reagent opens up new avenues for exploration in biotechnological applications.

1. Tris(pentafluorophenyl)borane-Catalyzed Reactions Using Silanes
Taylor Hackel, Nicholas A McGrath Molecules. 2019 Jan 25;24(3):432. doi: 10.3390/molecules24030432.
The utility of an electron-deficient, air stable, and commercially available Lewis acid tris(pentafluorophenyl)borane has recently been comprehensively explored. While being as reactive as its distant cousin boron trichloride, it has been shown to be much more stable and capable of catalyzing a variety of powerful transformations, even in the presence of water. The focus of this review will be to highlight those catalytic reactions that utilize a silane as a stoichiometric reductant in conjunction with tris(pentafluorophenyl) borane in the reduction of alcohols, carbonyls, or carbonyl-like derivatives.
2. Boric Acid, a Lewis Acid With Unique and Unusual Properties: Formulation Implications
Antonio Lopalco, Angela A Lopedota, Valentino Laquintana, Nunzio Denora, Valentino J Stella J Pharm Sci. 2020 Aug;109(8):2375-2386. doi: 10.1016/j.xphs.2020.04.015. Epub 2020 Apr 27.
This review provides insight into the use of boric acid as a pharmaceutical, a buffer, and an adjuvant/excipient in pharmaceutical formulations. Boric acid is a Lewis acid with a pKa of 8.92-9.24 that is sensitive to temperature, ionic strength, and concentration. The pKa varies with concentration because of polymerization above 0.02 M. Boric acid reacts reversibly with alcohols, especially 1,2-diols including carbohydrates, with carboxylic acids, thiols, and amines. These esters/adducts, are also Lewis acids with lower pKa values. Boric acid can stabilize some materials while catalyzing the degradation of others. Boric acid is used in various dermal and women's hygiene products because of its mild antibacterial and antifungal activity. In ophthalmic products, it is used as a buffer and in combination with other preservatives to broaden the prservative spectrum. Boric acid has been used reluctantly in parenteral products but appears to be quite safe at low doses. However, at high exposure, toxicity, including death, has been reported in humans, especially in children. Animal toxicities have also been noted, including reductions in male sperm counts. Boric acid is well absorbed on oral dosing. Its biological half-life is about 21 h in humans and has an affinity for some tissues, especially bone.
3. The phosphate ester group in secondary metabolites
Franco Della-Felice, Aloisio de Andrade Bartolomeu, Ronaldo Aloise Pilli Nat Prod Rep. 2022 May 26;39(5):1066-1107. doi: 10.1039/d1np00078k.
Covering: 2000 to mid-2021The phosphate ester is a versatile, widespread functional group involved in a plethora of biological activities. Its presence in secondary metabolites, however, is relatively rare compared to other functionalities and thus is part of a rather unexplored chemical space. Herein, the chemistry of secondary metabolites containing the phosphate ester group is discussed. The text emphasizes their structural diversity, biological and pharmacological profiles, and synthetic approaches employed in the phosphorylation step during total synthesis campaigns, covering the literature from 2000 to mid-2021.
Online Inquiry
Inquiry Basket