798576-99-5

Usage

Uses

Used in Pharmaceutical and Biochemical Research:
FMOC aminotriacid is used as a protecting group in the synthesis of peptides for the controlled assembly of peptide chains. It safeguards specific functional groups and amino acids, ensuring the successful formation of the desired peptide structure.
Used in Biotechnological Research:
FMOC aminotriacid is used as a fluorescent label for the detection and purification of peptides. This feature is valuable in biotechnological research, as it aids in the identification and isolation of specific peptide sequences.
Used in the Development of New Pharmaceuticals:
FMOC aminotriacid is used as a versatile tool in the development of new pharmaceuticals and biologically active compounds. Its role in peptide synthesis and protection of functional groups contributes to the creation of innovative and effective drug candidates.

Upstream product

• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 136586-99-7 4-amino-4-(2-tert-butoxycarbonylethyl)heptanedioic acid di-tertbutyl ester 
• 136587-00-3 di-tert-butyl 4-<2-(tert-butoxycarbonyl)ethyl>-4-nitroheptanedicarboxylate 
• 1217553-84-8 4-(2-tert-butoxycarbonyl-ethyl)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-heptanedioic acid di-tert-butyl ester 

Downstream Products

• 1260095-56-4 9H-fluoren-9-ylmethyl 1,7-bis(3,5-bis(methoxymethyl)phenylamino)-4-(3-(3,5-bis(methoxymethyl)phenylamino)-3-oxopropyl)-1,7-dioxoheptan-4-ylcarbamate 
• 1260095-55-3 9H-fluoren-9-ylmethyl 1,7-bis(3-methoxymethylphenylamino)-4-(3-(3-methoxymethylphenylamino)-3-oxopropyl)-1,7-dioxoheptan-4-ylcarbamate 
• 1217553-87-1 C₄₃H₂₇F₁₂NO₈ 

Relevant academic research and scientific papers

CELL SURFACE RECEPTOR BINDING COMPOUNDS AND CONJUGATES

The present disclosure provides a class of compounds including a ligand moiety that specifically binds to a cell surface receptor, such as a mannose-6-phosphate receptor (M6PR) or a cell surface asialoglycoprotein receptor (ASGPR). The cell surface M6PR or ASGPR binding compounds can trigger the receptor to internalize into the cell a bound compound. The ligand moieties of this disclosure can be linked to a variety of moieties of interest without impacting the specific binding to, and function of, the cell surface receptor, e.g., M6PR or ASGPR. Also provided are compounds that are conjugates of the ligand moieties linked to a biomolecule, such as an antibody, which conjugates can harness cellular pathways to remove specific proteins of interest from the cell surface or from the extracellular milieu. Also provided are methods of using the conjugates to target a polypeptide of interest for sequestration and/or lysosomal degradation.

Shell Cross-Linked Micelles as Nanoreactors for Enantioselective Three-Step Tandem Catalysis

Functionalized amphiphilic poly(2-oxazoline)-based triblock copolymers that assemble into shell cross-linked micelles (SCMs) are described. These micelles permit the site isolation of three incompatible catalysts through compartmentalization, thereby enabling three-step non-orthogonal tandem processes in one pot. In particular, the acid-catalyzed ketal hydrolysis to prochiral ketones proceeded in the hydrophilic corona, followed by the Rh-catalyzed asymmetric transfer hydrogenation to enantio-enriched alcohols in the cross-linked shell, and nucleophilic base-catalyzed acylation in the hydrophobic core. The catalysts are positioned in close proximity on a single micelle support to take advantage of the intramicellar substrate diffusion, yet they are sufficiently spaced apart from each other in physically distinct microenvironments. These compartmentalized micelles are substrate selective and, on a basic level, mimic compartmentalized catalytic architectures found in nature.

Structure-activity relationship studies on a Trp dendrimer with dual activities against HIV and enterovirus A71. Modifications on the amino acid

We have recently described a new class of dendrimers with tryptophan (Trp) on the surface that show dual antiviral activities against HIV and EV71 enterovirus. The prototype compound of this family is a pentaerythritol derivative with 12 Trps on the periphery. Here we complete the structure-activity relationship studies of this family to identify key features that might be significant for the antiviral activity. With this aim, novel dendrimers containing different amino acids (aromatic and non-aromatic), tryptamine (a “decarboxylated” analogue of Trp) and N-methyl Trp on the periphery have been prepared. Dendrimer with N-Methyl Trp was the most active against HIV-1 and HIV-2 while dendrimer with tyrosine was endowed with the most potent antiviral activity against EV71. This tyrosine dendrimer proved to inhibit a large panel of EV71 clinical isolates (belonging to different clusters) in the low nanomolar/high picomolar range. In addition, a new synthetic procedure (convergent approach) has been developed for the synthesis of the prototype and some other dendrimers. This convergent approach proved more efficient (higher yields, easier purification) than the divergent approach previously reported.

BLOCK COPOLYMERS AND THEIR CONJUGATES OR COMPLEXES WITH OLIGONUCLEOTIDES

Described herein are block copolymers, and methods of making and utilizing such copolymers. The described block copolymers are disruptive of a cellular membrane, including an extracellular membrane, an intracellular membrane, a vesicle, an organelle, an endosome, a liposome, or a red blood cell. Preferably, in certain instances, the block copolymer disrupts the membrane and enters the intracellular environment. In specific examples, the block copolymer is endosomolytic and capable of delivering an oligonucleotide (e.g., an mRNA) to a cell. Compositions comprising a block copolymer and an oligonucleotide (e.g., an mRNA) are also disclosed.

Modification of a dioxygen carrier, HemoCD, with PEGylated dendrons for extension of circulation time in the bloodstream

A supramolecular diatomic receptor, hemoCD, was modified with PEGylated dendrons to extend its circulation time in the bloodstream. The core component was 4-oxo-4-[[4-(10,15,20-tris(4-sulfonatophenyl)-21H,23H-porphin-5-yl)phenyl] amino]butanoic acid (Por-COOH). The building block of the dendrons was Fmoc-4-amino-4-(2-carboxyethyl)heptanedioic acid (FmocTA), which was condensed with α-amino-ω-methoxy-poly(ethylene glycol) (PEG 5000-NH2) to yield an FmocG1-dendron. After deprotection, the G1-dendron was condensed with Por-COOH to yield G1-Por. A precursor (FmocNA) of an FmocG2-dendron was prepared via a condensation reaction of 4-amino-4-(2-t-butoxycarbonylethyl)heptanedioic acid di-t-butyl ester (TA-E) with FmocTA followed by hydrolysis of the resultant nona-carboxylic acid nona-t-butyl ester. Condensation of FmocNA with PEG5000-NH 2 yielded an FmocG2-dendron. After deprotection, the G2-dendron was condensed with Por-COOH to yield G2-Por. The ferrous complexes of G1- and G2-Pors formed stable 1:1 inclusion complexes with Py3CD, a per-O-methylated β-cyclodextrin dimer with a pyridine linker, in aqueous solution yielding supramolecular complexes designated as G1-hemoCD and G2-hemoCD, respectively. Both G1- and G2-hemoCDs bound molecular oxygen, with the O2 affinities (P1/2) of hemoCD, G1-, and G2-hemoCDs at pH 7.4 and 37 C being 22, 20, and 20 Torr, respectively. The modification of hemoCD with the dendrons did not cause destabilization of the O2 adducts via autoxidation, as indicated by their half-lives (t1/2) of 6.8, 6.1, and 5.5 h for hemoCD, G1-, and G2-hemoCDs, respectively. The blood concentration-time curves of G1- and G2-hemoCDs injected into the bloodstream of rats exhibited two phases, with the half-lives of the fast and slow decays being 0.45 and 5.3 h, respectively, for G1-hemoCD, and 0.20 and 12.8 h, respectively, for G2-hemoCD. The half-lives of hemoCD were 0.02 and 0.50 h, respectively. The circulation time of hemoCD was markedly extended by its modification with the PEGylated dendrons, which was very effective in protecting hemoCD against opsonization for uptake by the reticuloendothelial system.

Efficient synthetic access to cationic dendrons and their application for ZnO nanoparticles surface functionalization: New building blocks for dye-sensitized solar cells

A new concept for the efficient synthesis of cationic dendrons, 4-tert-butyl-1-(3-(3,4-dihydroxybenzamido)benzyl)pyridinium bromide (17), 1,1′-(5-(3,4-dihydroxybenzamido)-1,3-phenylene)bis(methylene) bis(4-tert-butylpyridinium) bromide (18), N1,N7-bis(3-(

A versatile, modular platform for multivalent peptide ligands based on a dendritic wedge

A general methodology for the synthesis of multifunctional AB2, AB3, AB4, and AB5 dendritic wedges is described based on an orthogonal protection strategy. Asymmetric polyamide dendrons that possess N-terminal cysteine residues at the periphery were quantitatively functionalized with C-terminal thioester peptides using native chemical ligation. Conjugation of biologically relevant groups at the focal point resulted in a series of related structures with a highly controlled valency (2-5) that can directly be used in a systematic study on the strength of multivalent interactions. Using our modular approach various ligands, functional groups and spacers can readily be combined in order to generate a toolbox for the development of smart biomaterials used in molecular medicine and imaging.

Glyco-SAMs as glycocalyx mimetics: Synthesis of L-fucose- and D-mannose-terminated building blocks

In the course of a project on the supramolecular functions of the glycocalyx present on eukaryotic cell surfaces, it has been our goal to prepare spacer glycosides and cluster glycosides that are suitable for the formation of self-assembled monolayers (SAMs) on gold. We have selected amino-functionalized D-mannose and L-fucose derivatives for peptide coupling to thio-functionalised alkane and alkane-oligoethylene glycol spacers such as 12 and 15. Thus, a variety of thiospacered glycosides (16-19) and cluster glycosides (23, 24, 26, 28, and 29) were synthesized, which can be assembled on gold wafers to serve as glycocalyx mimetics. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.