| Catalog Number | ACM1325208250-1 |
|---|---|
| Product Name | Mal-PEG4-NHS ester |
| CAS Number | 1325208-25-0 |
| Synonyms | 4,7,10,13-Tetraoxapentadecanoic acid, 15-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-, 2,5-dioxo-1-pyrrolidinyl ester |
| IUPAC Name | (2,5-Dioxopyrrolidin-1-yl) 3-[2-[2-[2-[2-(2,5-dioxopyrrol-1-yl)ethoxy]ethoxy]ethoxy]ethoxy]propanoate |
| Molecular Weight | 442.4 |
| Molecular Formula | C19H26N2O10 |
| InChI | InChI=1S/C19H26N2O10/c22-15-1-2-16(23)20(15)6-8-28-10-12-30-14-13-29-11-9-27-7-5-19(26)31-21-17(24)3-4-18(21)25/h1-2H,3-14H2 |
| InChI Key | TUPOSLKVPPFQGR-UHFFFAOYSA-N |
| Boiling Point | 580.5±60.0 °C at 760 mmHg |
| Flash Point | 304.9±32.9 °C |
| Purity | >90% |
| Density | 1.4±0.1 g/cm3 |
| Appearance | Liquid |
| Storage | -20±5 ºC |
| Description | Mal-PEG4-NHS ester is a nonclaevable ADC linker containing a Maleimide group, 4-unit PEG and an NHS ester. |
| Complexity | 659 |
| Covalently-Bonded Unit Count | 1 |
| Exact Mass | 442.15874503 |
| Heavy Atom Count | 31 |
| Monoisotopic Mass | 442.15874503 |
| Type | Heterobifunctional PEG Linkers |
| Refractive Index | n20/D 1.547(lit.) |
| Topological Polar Surface Area | 138 Ų |
Kish, William. (2011).
Synthesis of high-efficiency affinity resin using Mal-PEG4-NHS ester
The synthesis of the affinity resin is a two-step process. First, the spacer arm is bound to the resin by forming an amide bond, where the NHS ester acts as a leaving group. The second reaction binds the HWRGWV-miniPEG-C to the maleimide group of the spacer arm. The added cysteine introduces a thiol functional group to the ligand, allowing the reaction to proceed in the pH range of 6.5-7.5, similar to similar cross-linking reactions. At pH 7, the maleimide group reacts 1,000 times faster with thiols than with amines.
The reaction scheme for generating the HWRGWV-miniPEG-C-PEGx-Toyopearl resin using Mal-PEG4-NHS will proceed in two steps. First, the Mal-PEG4-NHS will react with the primary amine on the resin to form an amide bond. Second, the thiol on the HWRGWV-miniPEG-C will attack the maleimide group of the spacer to form the target resin.
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