t-Boc-N-amido-PEG5-NHS ester

 CAS No.: 2055040-78-1  Cat No.: BP-500435  Purity: ≥95% 4.5  

t-Boc-N-amido-PEG5-NHS ester is a heterobifunctional PEG linker with a protected amine and an activated ester. Structurally, it contains an N-Boc-protected primary amine connected through PEG5 to a terminal NHS ester derived from propionic acid. The NHS ester reacts with primary amines to form an amide, while the N-Boc group masks the linker amine until acid-mediated deprotection is desired for a subsequent coupling step. In PROTAC and related targeted protein degradation research, the reagent enables ordered amide formation followed by exposure and functionalization of a second amine handle. Its defined architecture allows researchers to evaluate how linker polarity, flexibility, attachment sequence, and terminal-group selection influence conjugate preparation and the spatial requirements of productive target–E3 ligase engagement. Clear assignment of the protected and reactive groups also supports reproducible reaction planning and systematic comparison of alternative linker designs in research-focused targeted protein degradation workflows.

t-Boc-N-amido-PEG5-NHS ester

Structure of 2055040-78-1

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Category
PROTAC Linker
Molecular Formula
C22H38N2O11
Molecular Weight
506.55
Appearance
Pale Yellow Oily Matter

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

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Purity
≥95%
Solubility
Soluble in DMSO
Appearance
Pale Yellow Oily Matter
Storage
Store at 2-8°C for short term (days to weeks) or -20°C for long term (months to years)
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
(2,5-dioxopyrrolidin-1-yl) 3-[2-[2-[2-[2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]propanoate
Synonyms
BocNH-PEG5-CH2CH2COONHS; Boc-N-PEG5-C2-NHS ester; 2,5-dioxopyrrolidin-1-yl 2,2-dimethyl-4-oxo-3,8,11,14,17,20-hexaoxa-5-azatricosan-23-oate; 2-Methyl-2-propanyl {18-[(2,5-dioxo-1-pyrrolidinyl)oxy]-18-oxo-3,6,9,12,15-pentaoxaoctadec-1-yl}carbamate; Carbamic acid, N-[18-[(2,5-dioxo-1-pyrrolidinyl)oxy]-18-oxo-3,6,9,12,15-pentaoxaoctadec-1-yl]-, 1,1-dimethylethyl ester
Density
1.2±0.1 g/cm3
InChI Key
FCVPAOUCTNORCY-UHFFFAOYSA-N
InChI
InChI=1S/C22H38N2O11/c1-22(2,3)34-21(28)23-7-9-30-11-13-32-15-17-33-16-14-31-12-10-29-8-6-20(27)35-24-18(25)4-5-19(24)26/h4-17H2,1-3H3,(H,23,28)
SMILES
CC(C)(C)OC(=O)NCCOCCOCCOCCOCCOCCC(=O)ON1C(=O)CCC1=O

t-Boc-N-amido-PEG5-NHS ester, is designed to enable efficient conjugation between targeting ligands and protein-binding moieties through a PEG-based spacer and an NHS-activated amine-reactive handle. Its flexible poly(ethylene glycol) architecture can help tune linker length, solubility, and presentation of functional groups for ternary complex formation. The following sections describe the structure and the practical reactivity features relevant to PROTAC assembly.

Structure: The linker contains a Boc-protected amide segment and a poly(ethylene glycol) spacer terminating in an N-hydroxysuccinimide ester. It features an amide linkage, an NHS-activated ester for acyl transfer chemistry, and ether-rich PEG units that confer hydrophilicity and conformational flexibility.

Reactivity: The NHS ester reacts with primary amines to form stable amide bonds under mildly basic aqueous or mixed solvent conditions. Typical PROTAC synthesis uses buffered media that maintain amine nucleophilicity while minimizing hydrolysis of the activated ester. After coupling, Boc deprotection can be performed under standard acidolysis conditions when an unmasked amine is required for subsequent steps.

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* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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g/mol
Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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