DSPE-PEG4-DBCO

 CAS No.: 2112738-14-2  Cat No.: BP-501081  Purity: 95% 4.5  

DSPE-PEG4-DBCO is an amphiphilic PROTAC linker built from a phospholipid anchor (DSPE) conjugated to a short, hydrophilic polyethylene glycol spacer (PEG4) terminating in a strained cyclooctyne (DBCO) for copper-free azide–alkyne cycloaddition. The DSPE moiety provides membrane affinity and improves the local concentration of the linker at lipid interfaces, while the PEG4 segment supplies conformational flexibility to reduce steric hindrance during target engagement. In PROTAC or targeted degradation workflows, this linker is used to modularly connect an azide-bearing ligand (e.g., a warhead for a target protein or an E3 ligase binder) to an alkyne-bearing partner under mild conditions, enabling rapid assembly of degraders with controlled stoichiometry. Its lipophilic anchoring and bioorthogonal reactivity make it valuable for designing membrane-proximal or cell-surface–localized degradation systems and for optimizing linker placement to balance ternary complex formation and degradation potency.

DSPE-PEG4-DBCO

Structure of 2112738-14-2

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Category
PROTAC Linker
Molecular Formula
C₇₁H₁₁₆N₃O₁₅P
Molecular Weight
1282.67

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

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Purity
95%
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
[(2R)-3-[2-[3-[2-[2-[2-[3-[[3-(2-azatricyclo[10.4.0.04,9]hexadeca-1(16),4,6,8,12,14-hexaen-10-yn-2-yl)-3-oxopropyl]amino]-3-oxopropoxy]ethoxy]ethoxy]ethoxy]propanoylamino]ethoxy-hydroxyphosphoryl]oxy-2-octadecanoyloxypropyl] octadecanoate
Synonyms
(2-{1-[(3-{2-azatricyclo[10.4.0.0,hexadeca-1(16),4,6,8,12,14-hexaen-10-yn-2-yl}-3-oxopropyl)carbamoyl]-3,6,9,12-tetraoxapentadecan-15-amido}ethoxy)[(2R)-2,3-bis(octadecanoyloxy)propoxy]phosphinic acid
InChI Key
RIQFURRJENJBHO-IDKUVDLHSA-N
InChI
InChI=1S/C71H116N3O15P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-41-70(78)86-60-65(89-71(79)42-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)61-88-90(80,81)87-52-49-73-68(76)47-51-83-54-56-85-58-57-84-55-53-82-50-46-67(75)72-48-45-69(77)74-59-64-39-34-33-37-62(64)43-44-63-38-35-36-40-66(63)74/h33-40,65H,3-32,41-42,45-61H2,1-2H3,(H,72,75)(H,73,76)(H,80,81)/t65-/m1/s1
SMILES
CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(O)OCCNC(=O)CCOCCOCCOCCOCCC(=O)NCCC(=O)N1CC2=CC=CC=C2C#CC3=CC=CC=C31)OC(=O)CCCCCCCCCCCCCCCCC

DSPE-PEG4-DBCO is a bifunctional PROTAC linker designed to combine a lipid-anchoring DSPE segment with a PEG spacer and a DBCO click handle. This architecture supports modular conjugation, improved solubility, and efficient assembly of multicomponent degradation platforms. The DBCO functionality enables copper-free strain-promoted azide–alkyne cycloaddition (SPAAC), facilitating reliable coupling of PROTAC ligands or other targeting moieties under mild conditions. Detailed structural and reactivity considerations are provided below.

Structure: The linker contains a phospholipid (DSPE) hydrophobic anchor, a short polyethylene glycol segment for aqueous compatibility, and a cyclooctyne (DBCO) moiety for click reactivity. It features ester and ether linkages within the lipid–PEG framework and a strained alkyne embedded in a rigid cyclic system.

Reactivity: DBCO reacts with azide-functional partners via SPAAC, proceeding through a cycloaddition mechanism that forms a stable triazole linkage without requiring copper catalysts. Suitable conditions typically use aqueous or mixed solvent buffers compatible with biomolecules, maintaining neutral to mildly controlled pH and avoiding strong nucleophiles that could interfere with reactive intermediates. No special catalysts are required; reaction progress is commonly monitored by analytical methods such as LC-MS or gel-based assays.

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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

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