108466-89-3

Basic information

• Product Name: 3,8,11-Trioxa-5-azatridecan-13-oic acid, 2,2-diMethyl-4-oxo-
• Synonyms: 3,8,11-Trioxa-5-azatridecan-13-oic acid, 2,2-diMethyl-4-oxo-;8-tert-butyloxycarbonylaMino-3,6-dioxaoctanoic acid;2,2-DiMethyl-4-oxo-3,8,11-trioxa-5-azatridecan-13-oic acid;2-[2-[2-[(2-Methylpropan-2-yl)oxycarbonylaMino]ethoxy]ethoxy]acetic acid;t-Boc-N-amido-PEG2-CH2CO2H;Boc-N-amido-PEG2-CH2CO2H;t-boc-N-amido-PEG2-acetic acid;BocNH-PEG2-CH2COOH
• CAS NO: 108466-89-3
• Molecular Formula: C11H21NO6
• Molecular Weight: 263.28754
• Mol File: 108466-89-3.mol
• Article Data: 61

Chemical Properties

• Boiling Point: 425.7±30.0 °C(Predicted)
• Appearance: /
• Density: 1.145±0.06 g/cm3(Predicted)
• Storage Temp.: -20°C
• PKA: 3.40±0.10(Predicted)
• CAS DataBase Reference: 3,8,11-Trioxa-5-azatridecan-13-oic acid, 2,2-diMethyl-4-oxo-(CAS DataBase Reference)
• NIST Chemistry Reference: 3,8,11-Trioxa-5-azatridecan-13-oic acid, 2,2-diMethyl-4-oxo-(108466-89-3)
• EPA Substance Registry System: 3,8,11-Trioxa-5-azatridecan-13-oic acid, 2,2-diMethyl-4-oxo-(108466-89-3)

Safety Data

• Hazardous Substances Data: 108466-89-3(Hazardous Substances Data)

Usage

Description

t-Boc-N-amido-PEG2-CH2CO2H is a PEG linker containing a terminal carboxylic acid and Boc-protected amino group. The hydrophilic PEG spacer increases solubility in aqueous media. The terminal carboxylic acid can react with primary amine groups in the presence of activators (e.g. EDC, or HATU) to form a stable amide bond. The Boc group can be deprotected under mild acidic conditions to form the free amine.

Uses

t-Boc-N-amido-PEG2-CH2CO2H is a heterobifunctional, PEGylated crosslinker featuring a Boc-protected amine at one end and a carboxyl group at the other. The hydrophillic PEG linker facilitates solubility in biological applications. t-Boc-N-amido-PEG2-CH2CO2H can be used for bioconjugation or as a building block for synthesis of small molecules, conjugates of small molecules and/or biomolecules, or other tool compounds for chemical biology and medicinal chemistry that require ligation. Examples of applications include its synthetic incorporation into antibody-drug conjugates or proteolysis-targeting chimeras (PROTAC? molecules) for targeted protein degradation.

Upstream product

• 79-08-3 bromoacetic acid 
• 139115-91-6 2-(2-tert-butyloxycarbonylaminoethoxy)ethanol 
• 85623-52-5 C₃₆H₆₀O₃₀*C₅H₁₂O 
• 114429-15-1 C₃₆H₆₀O₃₀*C₅H₁₂O 
• 114466-04-5 C₃₆H₆₀O₃₀*C₅H₁₂O 
• 114429-11-7 C₃₆H₆₀O₃₀*C₄H₁₀O 
• 114429-10-6 α-cyclodextrin * 1-butanol 
• 124214-87-5 α-Cyclodextrin-n-Capronsaeure-Komplex 
• 305-53-3 monosodium iodoacetate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 134978-97-5 [2-(N-2-amino ethoxy)ethoxy] acetic acid 
• 560088-79-1 dicyclohexylammonium 1-(tert-butyloxycarbonylamino)-3,6-dioxa-octanoate 
• 134979-01-4 2-(2-(2-amino-ethoxy)ethoxy)acetic acid hydrochloride 
• 1254054-91-5 C₁₈H₂₇NO₆ 

Downstream Products

• 1310327-56-0 1-((R)-9-amino-4-(2,2-diphenylacetamido)-1-(4-hydroxyphenyl)-3,11-dioxo-13,16-dioxa-2,8,10-triazaoctadec-9-en-18-yl)-4-((E)-2-(1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinolin-9-yl)ethenyl)-2,6-dimethylpyridinium hydrotrifluoroacetate trifluoroacetate 
• 1310327-62-8 1-((R)-9-amino-4-(2,2-diphenylacetamido)-1-(4-hydroxyphenyl)-3,11-dioxo-13,16-dioxa-2,8,10-triazaoctadec-9-en-18-yl)-4-((1E,3E)-4-(4-(dimethylamino)phenyl)buta-1,3-dienyl)-2,6-dimethylpyridinium hydrotrifluoroacetate trifluoroacetate 
• 1254054-91-5 C₁₈H₂₇NO₆ 

Relevant articles and documents

Synthesis, Biological Evaluation of Fluorescent 23-Hydroxybetulinic Acid Probes, and Their Cellular Localization Studies

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Cell-Surface Receptor-Ligand Interaction Analysis with Homogeneous Time-Resolved FRET and Metabolic Glycan Engineering: Application to Transmembrane and GPI-Anchored Receptors

Ligand-binding assays are the linchpin of drug discovery and medicinal chemistry. Cell-surface receptors and their ligands have traditionally been characterized by radioligand-binding assays, which have low temporal and spatial resolution and entail safety risks. Here, we report a powerful alternative (GlycoFRET), where terbium-labeled fluorescent reporters are irreversibly attached to receptors by metabolic glycan engineering. For the first time, we show time-resolved fluorescence resonance energy transfer between receptor glycans and fluorescently labeled ligands. We describe GlycoFRET for a GPI-anchored receptor, a G-protein-coupled receptor, and a heterodimeric cytokine receptor in living cells with excellent sensitivity and high signal-to-background ratios. In contrast to previously described methods, GlycoFRET does not require genetic engineering or antibodies to label receptors. Given that all cell-surface receptors are glycosylated, we expect that GlycoFRET can be generalized with applications in chemical biology and biotechnology, such as target engagement, receptor pharmacology, and high-throughput screening.

Polyethylene glycol coupling medicine as well as preparation method and application thereof

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Design, Synthesis, and Evaluation of VHL-Based EZH2 Degraders to Enhance Therapeutic Activity against Lymphoma

Traditional EZH2 inhibitors are developed to suppress the enzymatic methylation activity, and they may have therapeutic limitations due to the nonenzymatic functions of EZH2 in cancer development. Here, we report proteolysis-target chimera (PROTAC)-based EZH2 degraders to target the whole EZH2 in lymphoma. Two series of EZH2 degraders were designed and synthesized to hijack E3 ligase systems containing either von Hippel-Lindau (VHL) or cereblon (CRBN), and some VHL-based compounds were able to mediate EZH2 degradation. Two best degraders, YM181 and YM281, induced robust cell viability inhibition in diffuse large B-cell lymphoma (DLBCL) and other subtypes of lymphomas, outperforming a clinically used EZH2 inhibitor EPZ6438 (tazemetostat) that was only effective against DLBCL. The EZH2 degraders displayed promising antitumor activities in lymphoma xenografts and patient-derived primary lymphoma cells. Our study demonstrates that EZH2 degraders have better therapeutic activity than EZH2 inhibitors, which may provide a potential anticancer strategy to treat lymphoma.

Method for synthesizing semaglutide side chain in liquid-phase convergent manner

The invention discloses a method for synthesizing a semaglutide side chain 1 in a liquid-phase convergent manner. The method comprises the steps: protecting amino of a raw material 2-(2-aminoethoxy)ethanol by using R1; then carrying out nucleophilic substitution reaction with ethyl bromoacetate; carrying out ester hydrolysis in one pot to obtain a compound 4; protecting carboxyl of the compound 4with R2; removing R1 to obtain a compound 6; carrying out condensation reaction on the compound 6 and fluorenylmethoxycarbonyl-L-glutamic acid 1-tert-butyl ester, to obtain a compound 8; removing R2 of the compound 8, and carrying out a coupling reaction with the compound 6 to obtain a compound 10; removing Fmoc of the compound 10, carrying out an amidation condensation coupling reaction with 18-(tert-butoxy)-18-oxooctadecanoic acid to obtain a compound 13; and removing R2 of the compound 13 to obtain the product 1. The method has the advantages of effective and controllable synthesis process,low cost and high yield, and can be suitable for large-scale production.