N-(Azido-PEG2)-N-Boc-PEG4-NHS ester

 CAS No.: 2093153-95-6  Cat No.: BP-500903  Purity: 98% 4.5  

N-(Azido-PEG2)-N-Boc-PEG4-NHS ester is a multifunctional, heterobifunctional PEG-based PROTAC linker designed for controlled conjugation chemistry. Structurally, it contains an NHS ester for efficient reaction with primary amines on target-binding ligands, a protected amine (Boc) that can be deprotected to enable subsequent coupling steps, and a terminal azide handle for orthogonal bioorthogonal labeling or click-mediated attachment to a second component. The PEG segments provide aqueous solubility and conformational flexibility, helping to reduce steric interference and to tune the effective distance between the ligands that recruit an E3 ligase and the target protein. In targeted protein degradation research, this linker enables modular assembly of PROTACs by first installing the NHS-activated portion onto an amine-functionalized ligand, then using the azide to connect the remaining module under conditions compatible with sensitive biomolecules. Its orthogonality and tunable spacing make it valuable for systematic optimization of degrader architectures and for generating fluorescent or affinity-tagged intermediates.

N-(Azido-PEG2)-N-Boc-PEG4-NHS ester

Structure of 2093153-95-6

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Category
PROTAC Linker
Molecular Formula
C₂₆H₄₅N₅O₁₂
Molecular Weight
619.66

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

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Purity
98%
Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
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Room temperature in continental US; may vary elsewhere.
IUPACName
(2,5-dioxopyrrolidin-1-yl) 3-[2-[2-[2-[2-[2-[2-(2-azidoethoxy)ethoxy]ethyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]ethoxy]ethoxy]ethoxy]ethoxy]propanoate
Synonyms
N-(AZIDO-PEG2)-N-BOC-PEG4-NHSESTER; 2,5-dioxopyrrolidin-1-yl 1-(13-azido-2,2-dimethyl-4-oxo-3,8,11-trioxa-5-azatridecan-5-yl)-3,6,9,12-tetraoxapentadecan-15-oate; 2,5-dioxopyrrolidin-1-yl 1-azido-9-(tert-butoxycarbonyl)-3,6,12,15,18,21-hexaoxa-9-azatetracosan-24-oate
InChI Key
JLYRAESBBJMWBK-UHFFFAOYSA-N
InChI
InChI=1S/C26H45N5O12/c1-26(2,3)42-25(35)30(8-12-38-16-15-37-11-7-28-29-27)9-13-39-17-19-41-21-20-40-18-14-36-10-6-24(34)43-31-22(32)4-5-23(31)33/h4-21H2,1-3H3
SMILES
CC(C)(C)OC(=O)N(CCOCCOCCN=[N+]=[N-])CCOCCOCCOCCOCCC(=O)ON1C(=O)CCC1=O

N-(Azido-PEG2)-N-Boc-PEG4-NHS ester, is designed to enable modular assembly of targeted protein degraders by combining an NHS-ester handle for efficient conjugation with an azide-bearing PEG segment for subsequent bioorthogonal coupling. Its PEG-rich architecture supports aqueous solubility and flexible spacer behavior, which can improve linker presentation and conjugate accessibility in PROTAC constructs. The details below describe its structure and the practical reactivity profile for PROTAC synthesis.

Structure: The molecule contains an NHS ester for acyl transfer, a Boc-protected amine for controlled deprotection, and a terminal azide for click-type chemistry. Multiple ethylene glycol units provide a hydrophilic, flexible PEG spacer. It features amide and carbamate linkages, with an overall amphiphilic character suitable for aqueous conjugation workflows.

Reactivity: The NHS ester reacts with primary amines under mildly basic aqueous or mixed solvent conditions to form stable amide bonds, enabling attachment to lysine-containing ligands or engineered amine-bearing targeting modules. The azide group is compatible with strain-promoted or Cu(I)-catalyzed azide–alkyne cycloaddition for orthogonal installation of the complementary partner. Boc can be removed using standard acid-mediated deprotection when required for further coupling, while the azide remains stable under typical NHS-ester conjugation conditions.

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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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