Fmoc-L-aspartic acid a-allyl ester
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Fmoc-L-aspartic acid a-allyl ester

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Category
Fmoc-Amino Acids
Catalog number
BAT-003734
CAS number
144120-53-6
Molecular Formula
C22H21NO6
Molecular Weight
395.40
Fmoc-L-aspartic acid a-allyl ester
IUPAC Name
(3S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxo-4-prop-2-enoxybutanoic acid
Synonyms
Fmoc-L-Asp-OAll; FMOC-ASP-OAL; (S)-3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(allyloxy)-4-oxobutanoic acid; Fmoc-L-Asp(OAll)-OH; FMOC-ASP-ALLYL ESTER
Appearance
White crystalline powder
Purity
≥ 98% (HPLC)
Density
1.286±0.06 g/cm3
Melting Point
119-125 °C
Boiling Point
634.8±55.0 °C
Storage
Store at -20 °C
InChI
InChI=1S/C22H21NO6/c1-2-11-28-21(26)19(12-20(24)25)23-22(27)29-13-18-16-9-5-3-7-14(16)15-8-4-6-10-17(15)18/h2-10,18-19H,1,11-13H2,(H,23,27)(H,24,25)/t19-/m0/s1
InChI Key
ZJMVIWUCCRKNHY-IBGZPJMESA-N
Canonical SMILES
C=CCOC(=O)C(CC(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13

Fmoc-L-aspartic acid α-allyl ester is a chemical reagent used primarily in peptide synthesis and research. Here are some key applications of Fmoc-L-aspartic acid α-allyl ester:

Peptide Synthesis: Fmoc-L-aspartic acid α-allyl ester is employed as a building block in the solid-phase synthesis of peptides. The Fmoc group protects the amino terminus while the α-allyl ester protects the carboxyl group, both of which can be selectively removed when needed. This allows for the sequential addition of amino acids to assemble complex peptide chains with high precision.

Protein Engineering: In protein engineering, Fmoc-L-aspartic acid α-allyl ester is used to introduce aspartic acid residues into synthetic peptides or modified proteins. This reagent enables site-specific incorporation of aspartic acid at designated positions, which can affect protein structure and function. Such modifications are crucial for studying protein activity, stability, and interactions.

Drug Development: Fmoc-L-aspartic acid α-allyl ester is valuable in the development of peptide-based therapeutics. By incorporating this reagent into drug candidates, researchers can investigate how aspartic acid residues influence the pharmacokinetic and pharmacodynamic properties of peptide drugs. This helps in optimizing peptide drug design for improved efficacy and stability.

Bioconjugation: In bioconjugation techniques, Fmoc-L-aspartic acid α-allyl ester can be used to link peptides to other molecules, such as polymers, drugs, or fluorescent probes. The α-allyl ester provides a reactive handle for coupling reactions, enabling the creation of multifunctional bioconjugates. These conjugates can be used in diagnostic assays, targeted drug delivery, and imaging applications.

1. 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.
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. 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.
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