18934-81-1

Basic information

• Product Name: BOC-12-ADO-OH
• Synonyms: 12-(BOC-AMINO)DODECANOIC ACID;BOC-12-ADO-OH;BOC-12-AMINODODECANOIC ACID;BOC-12-AMINOLAURIC ACID;BOC-NH-(CH2)11-COOH;N-TERT-BUTYLOXYCARBONYL-12-AMINO-DODECANOIC ACID;T-BUTOXYCARBONYL-12-AMINODODECANOIC ACID;T-BUTOXYCARBONYL-12-AMINOLAURIC ACID
• CAS NO: 18934-81-1
• Molecular Formula: C₁₇H₃₃NO₄
• Molecular Weight: 315.45
• Product Categories: Amino Acids
• Mol File: 18934-81-1.mol
• Article Data: 31

Chemical Properties

• Melting Point: 83.5-84.5 °C
• Boiling Point: 454.5±18.0 °C(Predicted)
• Appearance: /
• Density: 0.997±0.06 g/cm3(Predicted)
• Storage Temp.: Store at 0°C
• PKA: 4.78±0.10(Predicted)
• BRN: 1980302
• CAS DataBase Reference: BOC-12-ADO-OH(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-12-ADO-OH(18934-81-1)
• EPA Substance Registry System: BOC-12-ADO-OH(18934-81-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 18934-81-1(Hazardous Substances Data)

Usage

Description

BOC-12-ADO-OH, also known as Boc-12-Ado-OH, is a synthetic molecule that serves as a versatile linker in the development of protein degrader molecules, known as proteolysis-targeting chimeras (PROTACs). It features an alkane chain with a terminal carboxylic acid and Boc-protected amino groups, which can be utilized in various chemical reactions to create stable amide bonds and deprotected free amines.

Uses

Used in Pharmaceutical Industry:
BOC-12-ADO-OH is used as a PROTAC linker for the synthesis of protein degraders, which are a novel class of therapeutics designed to selectively target and degrade specific proteins within cells. The terminal carboxylic acid of BOC-12-ADO-OH can react with primary amine groups in the presence of activators, such as EDC or HATU, to form a stable amide bond. This property makes it a valuable component in the development of targeted protein degradation therapies.
Additionally, the Boc group in BOC-12-ADO-OH can be deprotected under mild acidic conditions, allowing for the formation of free amines. This feature further enhances the molecule's utility in the synthesis of various biologically active compounds and drug candidates.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 693-57-2 12-Aminododecanoic acid 
• 1031684-74-8 12-(N-tert-butoxycarbonyl)aminododecanoic acid methyl ester 

Downstream Products

• 947-04-6 2-azacyclotridecanone 
• 67341-03-1 N-(tent-butoxycarbonyl)-12-hydroxydodecylamine 
• 906072-85-3 12-(tert-butylcarbamoyl)dodecyl-4-nitrophenyl-2,2-diphenylethyl phosphate 
• 906072-80-8 bis-N,N-(p-nitrophenyl-2,2-diphenylethyl-12-aminododecyl phosphate)fumaramide 
• 906072-82-0 bis-N,N-(p-nitrophenyl-2,2-diphenylethyl-12-aminododecyl phosphate)-2,5-dimethoxyterephthalamide 
• 1220710-00-8 12-(tert-butoxycarbonyl)amino-N-(1,3-diphenyl-1H-pyrazol-4-yl)dodecanamide 
• 1239724-12-9 5-(12-(tert-butoxycarbonylamino)dodecanamido)isophthalicacid 
• 943923-31-7 12-amino-N-(benzyloxy)dodecanamide 
• 943923-30-6 tert-butyl (12-(benzyloxyamino)-12-oxododecyl)carbamate 
• 943923-29-3 dicyclohexylammonium 12-((tert-butoxycarbonyl)amino)dodecanoate 
• 1420011-10-4 C₄₂H₅₈BrN₃O₇ 

Relevant articles and documents

Synthetic micelle sensitive to IR light via a two-photon process

A micellar assembly of molecules constituted of poly(ethylene glycol) as the hydrophilic component and 2-diazo-1,2-naphthoquinone as the hydrophobic component was shown to be destroyed in a two-photon photoreaction triggered by infrared light with release of an encapsulated fluorescent probe molecule. Copyright

Preparation and application of three-branch RGD modified brain glioma targeting lipid material

The invention discloses a three-branch RGD-modified glioma targeting lipid material which is used for targeted delivery of brain glioma treatment drugs. One end of the novel lipid material is connected with cholesterol extending through polyethylene glycol, and the other end of the novel lipid material is connected with RGD peptide with brain glioma targeting function, and the novel lipid material can be used for integrin receptor α which is highly expressed on the surface of brain capillary endothelial cells and brain glioma cells. v β3 The affinity between the brain glioma is achieved through the affinity between the brain glioma, and the effective concentration of the therapeutic drug to the brain tumor is improved. The novel lipid lipid material can be used for liposome. The prepared paclitaxel liposome has obvious brain targeting property and tumor targeting property, and has wide application prospects.

PROTAC-mediated degradation of class i histone deacetylase enzymes in corepressor complexes

We have identified a proteolysis targeting chimera (PROTAC) of class I HDACs 1, 2 and 3. The most active degrader consists of a benzamide HDAC inhibitor, an alkyl linker, and the von Hippel-Lindau E3 ligand. Our PROTAC increased histone acetylation levels and compromised colon cancer HCT116 cell viability, establishing a degradation strategy as an alternative to class I HDAC inhibition.

THERAPEUTIC METHODS

The invention provides methods and compositions for delivering a nucleic acid to a cell or the cytosol of the target cell. The method includes contacting the cell with, 1) a membrane-destabilizing polymer; and 2) a nucleic acid conjugate. The nucleic acid conjugate includes a targeting ligand bound to an optional linker and a nucleic acid.