DBCO-C3-PEG4-NH-Boc

 Cat No.: BP-501964  Purity: 98% 4.5  

DBCO-C3-PEG4-NH-Boc is a heterobifunctional PROTAC linker reagent combining a strained cyclooctyne (DBCO) for rapid copper-free azide–alkyne cycloaddition with a C3 spacer and a PEG4 segment that provides aqueous solubility and conformational flexibility. The linker terminates in an amine protected as a Boc carbamate, enabling subsequent deprotection and coupling to a recruiter or E3-ligase ligand through standard amide- or carbamate-forming chemistries. In targeted protein degradation workflows, this reagent is used to assemble modular PROTAC architectures by orthogonally connecting azide-bearing components (e.g., ligand–azide constructs) to DBCO-functionalized partners while minimizing steric hindrance and aggregation effects. Its PEG-based spacing and orthogonal click handle make it valuable for optimizing linker length, reducing nonspecific interactions, and improving the efficiency of ternary complex formation during experimental PROTAC synthesis and structure–activity studies.

DBCO-C3-PEG4-NH-Boc

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Category
PROTAC Linker
Molecular Formula
C₃₈H₅₁N₃O₁₀
Molecular Weight
709.83

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

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Purity
98%
Solubility
DMSO, DCM, DMF
Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
3-[[4-(2-azatricyclo[10.4.0.04,9]hexadeca-1(16),4,6,8,12,14-hexaen-10-yn-2-yl)-4-oxobutanoyl]amino]propyl 3-[2-[2-[2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethoxy]ethoxy]ethoxy]ethoxy]propanoate
InChI Key
UMONQRPDXRZGCO-UHFFFAOYSA-N
InChI
InChI=1S/C38H51N3O10/c1-38(2,3)51-37(45)40-19-22-47-24-26-49-28-27-48-25-23-46-21-17-36(44)50-20-8-18-39-34(42)15-16-35(43)41-29-32-11-5-4-9-30(32)13-14-31-10-6-7-12-33(31)41/h4-7,9-12H,8,15-29H2,1-3H3,(H,39,42)(H,40,45)
SMILES
CC(C)(C)OC(=O)NCCOCCOCCOCCOCCC(=O)OCCCNC(=O)CCC(=O)N1CC2=CC=CC=C2C#CC3=CC=CC=C31

This DBCO-functionalized PEG-based linker is designed for efficient, modular assembly of PROTAC constructs, enabling robust conjugation strategies that preserve linker flexibility and facilitate productive ternary complex formation. Its PEG spacer can improve solubility and reduce steric constraints between targeting and recruitment modules. The molecule will be described in detail below, including its structural features and practical guidance for PROTAC linker coupling and subsequent functionalization steps.

Structure: The linker contains a cyclooctyne (DBCO) handle connected through a flexible PEG chain to a protected amine (Boc). It features ether linkages within the PEG segment, carbamate protection at the terminal nitrogen, and a strained alkynyl moiety suitable for bioorthogonal cycloaddition.

Reactivity: The DBCO group undergoes strain-promoted azide–alkyne cycloaddition with azide-bearing partners under mild, catalyst-free conditions, making it compatible with sensitive PROTAC components. The Boc-protected amine is typically deprotected using standard acid-mediated conditions to generate a free amine for amide or urea coupling. Common coupling steps employ electrophiles such as activated carboxylic acids with base-promoted conditions in suitable organic solvents.

Stock concentration: *
Desired final volume: *
Desired concentration: *

L

* 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

* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
g/mol
g

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