Boc-NH-PEG5-Ms

 CAS No.: 2128735-28-2  Cat No.: BP-500350  Purity: ≥95% 4.5  

Boc-NH-PEG5-Ms is a Boc-protected amino-terminated polyethylene glycol linker bearing a methanesulfonate (Ms) leaving group, enabling efficient, site-selective functionalization in PROTAC and targeted protein degradation workflows. Structurally, it combines a terminal protected amine for controlled coupling chemistry with a five-unit PEG chain that provides aqueous solubility, conformational flexibility, and reduced non-specific hydrophobic interactions. The Ms group serves as an activated handle for substitution by nucleophiles (e.g., amines or related coupling partners), allowing users to install the linker between a ligand for an E3 ligase and a ligand for the target protein or to append additional spacer elements. In PROTAC design, the PEG segment can help tune effective molarity and spatial orientation, improving productive ternary complex formation while maintaining synthetic modularity. This linker is valuable for building degraders with reproducible attachment points and for optimizing linker length and polarity during iterative structure–activity studies.

Boc-NH-PEG5-Ms

Structure of 2128735-28-2

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PROTAC Linker
Molecular Formula
C16H33NO9S
Molecular Weight
415.49

* For research and manufacturing use only. Not for human or clinical use.

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Purity
≥95%
Storage
Store at 2-8°C
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
2-[2-[2-[2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethoxy]ethoxy]ethoxy]ethoxy]ethyl methanesulfonate
Synonyms
t-Boc-N-amido-PEG5-MS; Boc-N-Amido-PEG5-Ms; 2,2-Dimethyl-4-oxo-3,8,11,14,17-pentaoxa-5-azanonadecan-19-yl methanesulfonate; Carbamic acid, N-[14-[(methylsulfonyl)oxy]-3,6,9,12-tetraoxatetradec-1-yl]-, 1,1-dimethylethyl ester
Boiling Point
542.5±50.0°C at 760 mmHg
Density
1.2±0.1 g/cm3
InChI Key
XAHYLBKEJWWORN-UHFFFAOYSA-N
InChI
InChI=1S/C16H33NO9S/c1-16(2,3)26-15(18)17-5-6-21-7-8-22-9-10-23-11-12-24-13-14-25-27(4,19)20/h5-14H2,1-4H3,(H,17,18)
SMILES
CC(C)(C)OC(=O)NCCOCCOCCOCCOCCOS(=O)(=O)C

Boc-NH-PEG5-Ms is a PEG-based linker bearing a Boc-protected amine and a methanesulfonate (mesylate) leaving group, designed to facilitate modular assembly of targeted protein degraders. Its ether-rich, flexible scaffold supports productive spatial presentation between ligand components, while the activated mesylate enables efficient attachment chemistry under standard synthetic conditions. The Boc group provides orthogonal protection for controlled deprotection and subsequent coupling steps. Detailed structural and reactivity considerations are provided below.

Structure: Boc-protected amine is tethered to a poly(ethylene glycol) chain and terminated with a mesylate leaving group. The linker contains ether linkages along the PEG backbone, a carbamate from the Boc group, and a sulfonate ester at the reactive terminus. This combination yields a polar, flexible, and water-compatible scaffold.

Reactivity: The mesylate can undergo nucleophilic substitution with amines, thiols, or other suitable nucleophiles to form a new C–N or related bond for PROTAC construction. Reactions are typically performed under basic conditions with polar aprotic or mixed solvents to promote substitution while preserving the Boc group. Subsequent Boc deprotection enables further coupling, following established carbamate deprotection strategies compatible with PEG linkers.

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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