798576-99-5

Basic information

• Product Name: FMOC aminotriacid
• Synonyms: FMOC aminotriacid
• CAS NO: 798576-99-5
• Molecular Formula: C₂₅H₂₇NO₈
• Molecular Weight: 469.48378
• Mol File: 798576-99-5.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 775.0±60.0 °C(Predicted)
• Appearance: /
• Density: 1.352±0.06 g/cm3(Predicted)
• PKA: 4.05±0.10(Predicted)
• CAS DataBase Reference: FMOC aminotriacid(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC aminotriacid(798576-99-5)
• EPA Substance Registry System: FMOC aminotriacid(798576-99-5)

Safety Data

• Hazardous Substances Data: 798576-99-5(Hazardous Substances Data)

Usage

General Description

FMOC aminotriacid is a chemical compound commonly used in the field of organic and medicinal chemistry. It is a derivative of the FMOC (9-fluorenylmethoxycarbonyl) protecting group, and its structure consists of an aminotriacid molecule attached to the FMOC group. FMOC aminotriacid is useful in the synthesis of peptides and peptide conjugates due to its ability to protect specific functional groups and amino acids during the assembly of peptide chains. It also serves as a fluorescent label for the detection and purification of peptides, making it valuable in biochemical and biotechnological research. Overall, FMOC aminotriacid plays an important role in the efficient and controlled synthesis of peptides and is a versatile tool in the development of new pharmaceuticals and biologically active compounds.

Upstream product

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

Downstream Products

• 1217553-87-1 C₄₃H₂₇F₁₂NO₈ 
• 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 

Relevant articles and documents

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.

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.

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.