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Fmoc-D-alanine pentafluorophenyl 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-003630

CAS number

125043-04-1

Molecular Formula

C24H16F5NO4

Molecular Weight

477.40

IUPAC Name

(2,3,4,5,6-pentafluorophenyl) (2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoate

Synonyms

Fmoc-D-Ala-Opfp; (R)-Perfluorophenyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)propanoate

Appearance

White powder

Purity

≥ 97% (HPLC)

Density

1.426 g/cm3

Melting Point

173-179 °C

Boiling Point

574.1±50.0 °C(Predicted)

Storage

Store at 2-8°C

InChI

InChI=1S/C24H16F5NO4/c1-11(23(31)34-22-20(28)18(26)17(25)19(27)21(22)29)30-24(32)33-10-16-14-8-4-2-6-12(14)13-7-3-5-9-15(13)16/h2-9,11,16H,10H2,1H3,(H,30,32)/t11-/m1/s1

InChI Key

CJXZXBGKOSXBFR-LLVKDONJSA-N

Canonical SMILES

CC(C(=O)OC1=C(C(=C(C(=C1F)F)F)F)F)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

Fmoc-D-alanine pentafluorophenyl ester, a versatile reagent in peptide synthesis and various biochemical applications, serves a pivotal role in advancing scientific endeavors. Here are the key applications of this compound, presented with a high degree of perplexity and burstiness:

Peptide Synthesis: Employed as an activating agent in solid-phase peptide synthesis, Fmoc-D-alanine pentafluorophenyl ester facilitates the coupling of amino acids by forging crucial amide bonds. This process ensures the synthesis of peptides with efficiency and purity, especially beneficial in crafting intricate peptide structures containing D-amino acids.

Drug Discovery and Development: Within the realm of pharmaceutical research, Fmoc-D-alanine pentafluorophenyl ester plays a critical role in synthesizing peptide-based drug candidates. By incorporating D-alanine, this compound enhances the stability and bioavailability of therapeutic peptides. Scientists utilize this reagent to create novel peptide drugs with superior pharmacological properties, driving innovation in drug development.

Analytical Biochemistry: Integral to analytical biochemistry, this compound is utilized in generating standards for techniques like high-performance liquid chromatography (HPLC) and mass spectrometry. Fmoc-D-alanine pentafluorophenyl ester aids in labeling peptides and proteins, enabling precise detection and quantification. This precise characterization is essential for elucidating protein structures and unraveling post-translational modifications, paving the way for deeper insights in bioanalytical sciences.

Protein Engineering: In the domain of protein engineering, Fmoc-D-alanine pentafluorophenyl ester is harnessed to modify specific protein residues with precision. By incorporating D-alanine at specific sites, researchers delve into the impact of stereochemistry on protein functionality and stability. This strategic approach allows for the design of proteins with tailored properties for diverse applications in both research and industrial settings, pushing the boundaries of protein engineering capabilities.

1. Pd-Catalyzed Suzuki-Miyaura Cross-Coupling of Pentafluorophenyl Esters

Jonathan Buchspies, Daniel J Pyle, Huixin He, Michal Szostak Molecules. 2018 Nov 29;23(12):3134. doi: 10.3390/molecules23123134.

Although the palladium-catalyzed Suzuki-Miyaura cross-coupling of aryl esters has received significant attention, there is a lack of methods that utilize cheap and readily accessible Pd-phosphane catalysts, and can be routinely carried out with high cross-coupling selectivity. Herein, we report the first general method for the cross-coupling of pentafluorophenyl esters (pentafluorophenyl = pfp) by selective C⁻O acyl cleavage. The reaction proceeds efficiently using Pd(0)/phosphane catalyst systems. The unique characteristics of pentafluorophenyl esters are reflected in the fully selective cross-coupling vs. phenolic esters. Of broad synthetic interest, this report establishes pentafluorophenyl esters as new, highly reactive, bench-stable, economical, ester-based, electrophilic acylative reagents via acyl-metal intermediates. Mechanistic studies strongly support a unified reactivity scale of acyl electrophiles by C(O)⁻X (X = N, O) activation. The reactivity of pfp esters can be correlated with barriers to isomerization around the C(acyl)⁻O bond.

2. 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.

3. Pentafluorophenyl Ester-based Polymersomes as Nanosized Drug-Delivery Vehicles

Martin Scherer, Karl Fischer, Frank Depoix, Thomas Fritz, Raphael Thiermann, Kristin Mohr, Rudolf Zentel Macromol Rapid Commun. 2016 Jan;37(1):60-66. doi: 10.1002/marc.201500444. Epub 2015 Oct 19.

In this work, activated ester chemistry is employed to synthesize biocompatible and readily functionalizable polymersomes. Via aminolysis of pentafluorophenyl methacrylate-based precursor polymers, an N-(2-hydroxypropyl) methacrylamide (HPMA)-analog hydrophilic block is obtained. The precursor polymers can be versatile functionalized by simple addition of suitable primary amines during aminolysis as demonstrated using a fluorescent dye. Vesicle formation is proven by cryoTEM and light scattering. High encapsulation efficiencies for hydrophilic cargo like siRNA are achieved using dual centrifugation and safe encapsulation is demonstrated by gel electrophoresis. In vitro studies reveal low cytotoxicity and no protein adsorption-induced aggregation in human blood serum occurs, making the vesicles interesting candidates as nanosized drug carriers.