5,8,11,14-Tetraoxa-2-azahexadecanedioic acid
- Product Name
- 5,8,11,14-Tetraoxa-2-azahexadecanedioic acid
- CAS No.
- 437655-95-3
- Chemical Name
- 5,8,11,14-Tetraoxa-2-azahexadecanedioic acid
- Synonyms
- Fmoc-PEG4- CH2COOH;Fmoc-NH-PEG5-CH2CO2H;FMoc-NH-PEG4-CH2COOH;Fmoc-NH-PEG4-CH2CO2H;Fmoc-PEG4-acetic acid;Fmoc-N-Amido-PEG4-CH2COOH;Fmoc-N-amido-PEG4-acetic acid;5,8,11,14-Tetraoxa-2-azahexadecanedioic acid;1-Hydroxy-1-oxo-5,8,11,14-tetraoxa-2-azahexadecan-16-oic acid;1-(9H-Fluoren-9-yl)-3-oxo-2,7,10,13,16-pentaoxa-4-azaoctadecan-18-oic acid
- CBNumber
- CB62546849
- Molecular Formula
- C25H31NO8
- Formula Weight
- 473.52
- MOL File
- 437655-95-3.mol
5,8,11,14-Tetraoxa-2-azahexadecanedioic acid Property
- Melting point:
- 51℃
- Boiling point:
- 681.3±55.0 °C(Predicted)
- Density
- 1.235±0.06 g/cm3(Predicted)
- storage temp.
- 2-8°C
- form
- Oil
- pka
- 3.39±0.10(Predicted)
- color
- Colorless to light yellow
- InChI
- InChI=1S/C25H31NO8/c27-24(28)18-33-16-15-32-14-13-31-12-11-30-10-9-26-25(29)34-17-23-21-7-3-1-5-19(21)20-6-2-4-8-22(20)23/h1-8,23H,9-18H2,(H,26,29)(H,27,28)
- InChIKey
- XPNLDOFYRFOXLR-UHFFFAOYSA-N
- SMILES
- C(OCC1C2=C(C=CC=C2)C2=C1C=CC=C2)(=O)NCCOCCOCCOCCOCC(O)=O
Safety
- HS Code
- 2942000090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- CS-0105401
- Product name
- Fmoc-NH-PEG4-CH2COOH
- Packaging
- 100mg
- Price
- $60
- Updated
- 2021/12/16
- Product number
- CS-0105401
- Product name
- Fmoc-NH-PEG4-CH2COOH
- Packaging
- 250mg
- Price
- $100
- Updated
- 2021/12/16
- Product number
- AS110733
- Product name
- 1-(9H-Fluoren-9-yl)-3-oxo-2,7,10,13,16-pentaoxa-4-azaoctadecan-18-oic acid
- Purity
- 97%
- Packaging
- 250mg
- Price
- $174
- Updated
- 2021/12/16
- Product number
- CS-0105401
- Product name
- Fmoc-NH-PEG4-CH2COOH
- Packaging
- 1g
- Price
- $255
- Updated
- 2021/12/16
- Product number
- 280117
- Product name
- Fmoc-NH-PEG4-CH2COOH
- Purity
- >=95%
- Packaging
- 1g
- Price
- $287
- Updated
- 2021/12/16
5,8,11,14-Tetraoxa-2-azahexadecanedioic acid Chemical Properties,Usage,Production
Description
Fmoc-NH-PEG4-CH2COOH is a PEG linker containing an Fmoc-protected amine and a terminal carboxylic acid. The hydrophilic PEG spacer increases solubility in aqueous media. The Fmoc group can be deprotected under basic condition to obtain the free amine which can be used for further conjugations. 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.
Biological Activity
Fmoc-NH-PEG4-CH2COOH is a degradable ADC linker for antibody drug conjugate (ADC) synthesis. It is also a PEG-based PROTAC linker, which can be used for PROTAC synthesis.
Synthesis
195071-49-9
102774-86-7
437655-95-3
The general procedure for the synthesis of 1-(9H-fluoren-9-yl)-3-oxo-2,7,10,13,16-pentaoxa-4-azaoctadecan-18-oic acid from 14-amino-3,6,9,12-tetraoxatetradecane-1-oic acid and compounds (CAS: 102774-86-7) was as follows: 14-amino-3,6,9,12-tetraoxatetradecane -1-acid (0.79 g, 3.14 mmol) and K2CO3 (1.04 g, 7.50 mmol) were dissolved in 5.8 mL of water and stirred at room temperature for 15 minutes. Subsequently, N-(9-fluorenylmethoxycarbonyl)succinimide (Fmoc-OSu, 1.28 g, 3.79 mmol) was added, and stirring of the reaction mixture was continued for 24 h, during which the reaction progress was monitored by thin-layer chromatography (TLC, with unfolding agent ratio of CHCl3/MeOH/AcOH, 5:1:0.06). Upon completion of the reaction, the salts were removed by filtration and the filtrate was washed with ether (Et2O) and then acidified with 3N hydrochloric acid to pH 1. The acidified solution was used to extract the target compounds with dichloromethane (DCM). After the extraction was completed, the solvent was removed by distillation under reduced pressure and the resulting crude product was purified by reversed-phase high performance liquid chromatography (RP-HPLC). The fraction containing the target product was collected and lyophilized to give compound 11a (1.08 g, 73% yield). Compound 11a has the chemical formula C25H11NO8, theoretical mass-to-charge ratio [M + H]+ = 474.2, measured mass-to-charge ratio [M + H]+ = 474.9, [M + Na]+ = 496.9.
in vitro
ADCs are comprised of an antibody to which is attached an ADC cytotoxin through an ADC linker.
PROTACs contain two different ligands connected by a linker; one is a ligand for an E3 ubiquitin ligase and the other is for the target protein. PROTACs exploit the intracellular ubiquitin-proteasome system to selectively degrade target proteins.
target
| Cleavable
| Alkyl/ether
| PEGs
|
References
[1] Patent: US2018/169262, 2018, A1. Location in patent: Paragraph 0181-0183
5,8,11,14-Tetraoxa-2-azahexadecanedioic acid Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 5,8,11,14-Tetraoxa-2-azahexadecanedioic acid manufacturers
- Product
- Fmoc-NH-PEG4-CH2COOH 437655-95-3
- Price
- US $166.00/g
- Min. Order
- 1g
- Purity
- 98%
- Supply Ability
- 500kg
- Release date
- 2025-11-25
- Product
- 1-(9H-fluoren-9-yl)-3-oxo-2,7,10,13,16-pentaoxa-4-azaoctadecan-18-oic acid 437655-95-3
- Price
- US $0.00-0.00/g
- Min. Order
- 1g
- Purity
- 98%
- Supply Ability
- 1g/bottle, 10g/bottle, 100g/bottle
- Release date
- 2025-09-12
- Product
- Fmoc-NH-PEG4-CH2COOH 437655-95-3
- Price
- US $2.00-6.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 100kg
- Release date
- 2025-08-06