60142-89-4

Basic information

• Product Name: BOC-7-AMINO-HEPTANOIC ACID
• Synonyms: BOC-AHEPT-OH;BOC-7-AHP-OH;BOC-7-AMINO-HEPTANOIC ACID;BOC-NH-(CH2)6-COOH;7-(BOC-AMINO)ENANTHIC ACID;7-(BOC-AMINO)HEPTANOIC ACID;N-TERT-BUTYLOXYCARBONYL-7-AMINOHEPTANOIC ACID;N-T-BUTOXYCARBONYL-7-AMINOENANTHIC ACID
• CAS NO: 60142-89-4
• Molecular Formula: C₁₂H₂₃NO₄
• Molecular Weight: 245.32
• Product Categories: Unusual amino acids
• Mol File: 60142-89-4.mol
• Article Data: 17

Chemical Properties

• Melting Point: 56-60 °C
• Boiling Point: 393.1 °C at 760 mmHg
• Flash Point: 191.6 °C
• Appearance: /
• Density: 1.05g/cm3
• Vapor Pressure: 2.82E-07mmHg at 25°C
• Refractive Index: 1.464
• Storage Temp.: 2-8°C
• Solubility: soluble in Methanol
• PKA: 4.77±0.10(Predicted)
• BRN: 2050867
• CAS DataBase Reference: BOC-7-AMINO-HEPTANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-7-AMINO-HEPTANOIC ACID(60142-89-4)
• EPA Substance Registry System: BOC-7-AMINO-HEPTANOIC ACID(60142-89-4)

Safety Data

• Hazard Codes: Xi
• WGK Germany: 3
• F: 9-21
• HazardClass: IRRITANT
• Hazardous Substances Data: 60142-89-4(Hazardous Substances Data)

Usage

Description

BOC-7-AMINO-HEPTANOIC ACID, also known as Boc-7-Aminoheptanoic acid, is an alkane chain with a terminal carboxylic acid and Boc-protected amino groups. It is utilized in the synthesis of Proteolysis Targeting Chimeras (PROTACs) and other conjugation applications due to its ability to form stable amide bonds with primary amine groups in the presence of activators. The Boc group can be deprotected under mild acidic conditions, yielding the free amine.

Uses

Used in Pharmaceutical Industry:
BOC-7-AMINO-HEPTANOIC ACID is used as a PROTAC linker for the synthesis of Proteolysis Targeting Chimeras (PROTACs) to facilitate targeted protein degradation. This application is significant as it aids in the development of novel therapeutic strategies for various diseases, including cancer and neurodegenerative disorders, by promoting the selective degradation of specific proteins.
Used in Chemical Synthesis:
BOC-7-AMINO-HEPTANOIC ACID is used as a building block in chemical synthesis for creating various conjugates and complex molecules. The terminal carboxylic acid allows for the formation of stable amide bonds with primary amine groups, while the Boc-protected amino group ensures that the amine remains protected until the desired deprotection step, enhancing the versatility and specificity of the synthesis process.

InChI:InChI=1/C12H23NO4/c1-12(2,3)17-11(16)13-9-7-5-4-6-8-10(14)15/h4-9H2,1-3H3,(H,13,16)(H,14,15)

Upstream product

• 6627-89-0 tert-butyl phenyl carbonate 
• 929-17-9 7-aminoheptanoic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 76806-13-8 6-chlorohexan-1-amine hydrochloride 
• 4048-33-3 6-amino-1-hexanol 
• 124-38-9 carbon dioxide 
• 69825-10-1 (6-chlorohexyl)carbamic acid tert-butyl ester 
• 24608-52-4 tert-butyl chloroformate 
• 673-66-5 7-amino-heptanoic acid lactam 
• 116437-30-0 1-(tert-butoxycarbonyl)-1-azacyclooctan-2-one 

Downstream Products

• 239477-65-7 7-tert-butoxycarbonylamino-heptanoic acid 6-[3-(4-methoxy-benzyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester 
• 2306389-03-5 (2S,4R)-1-((S)-2-(7-aminoheptanamido)-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide 

Relevant articles and documents

Remote Amino Acid Recognition Enables Effective Hydrogen Peroxide Activation at a Manganese Oxidation Catalyst

Precise delivery of a proton plays a key role in O2 activation at iron oxygenases, enabling the crucial O?O cleavage step that generates the oxidizing high-valent metal–oxo species. Such a proton is delivered by acidic residues that may either

Vorinostat skeleton-based anthranilamide compound as well as preparation and application thereof

The invention provides a vorinostat skeleton-based anthranilamide compound as well as preparation and application of the anthranilamide compound. The structural formula of the o-aminobenzamide compound based on a vorinostat skeleton is shown in the specification, wherein n is equal to 1-6, and R is methylamino, dimethylamino, hydroxyl, NH2 or the like. The anthranilamide compound based on the vorinostat skeleton has the effect of inhibiting gastric cancer cell proliferation through MTT method determination, and can be used for preparing anti-gastric cancer drugs.

Selective Pseudo-irreversible Butyrylcholinesterase Inhibitors Transferring Antioxidant Moieties to the Enzyme Show Pronounced Neuroprotective Efficacy in Vitro and in Vivo in an Alzheimer's Disease Mouse Model

A series of multitarget-directed ligands (MTDLs) was designed by functionalizing a pseudo-irreversible butyrylcholinesterase (BChE) inhibitor. The obtained hybrids were investigated in vitro regarding their hBChE and hAChE inhibition, their enzyme kinetics, and their antioxidant physicochemical properties (DPPH, ORAC, metal chelating). In addition, in vitro assays were applied to investigate antioxidant effects using murine hippocampal HT22 cells and immunomodulatory effects on the murine microglial N9 cell line. The MTDLs retained their antioxidative properties compared to the parent antioxidant-moieties in vitro and the inhibition of hBChE was maintained in the submicromolar range. Representative compounds were tested in a pharmacological Alzheimer's disease (AD) mouse model and demonstrated very high efficacy at doses as low as 0.1 mg/kg. The most promising compound was also tested in BChE-/- mice and showed reduced efficacy. In vivo neuroprotection by BChE inhibition can be effectively enhanced by incorporation of structurally diverse antioxidant moieties.