DBCO-S-S-PEG3-biotin

 CAS No.: 1430408-09-5  Cat No.: BP-501040  Purity: >99% 4.5  

DBCO-S-S-PEG3-biotin is a heterobifunctional PROTAC linker built around a DBCO (dibenzocyclooctyne) cyclooctyne handle, a reducible disulfide (S–S) connection, a short PEG3 spacer, and a terminal biotin group. Structurally, the PEG3 segment provides aqueous solubility and spatial flexibility, while the disulfide linkage introduces a redox-responsive element that can be cleaved inside reducing environments, enabling controlled release or rearrangement of conjugates. In targeted protein degradation workflows, this linker is valuable for assembling PROTAC-related constructs by enabling strain-promoted azide–alkyne cycloaddition (SPAAC) to attach the DBCO moiety to an azide-bearing ligand or scaffold, while the biotin end can be used for affinity-based capture, purification, or orientation control via streptavidin/avidin systems. The reducible S–S architecture and modular conjugation strategy make it useful for studying how linker chemistry influences intracellular trafficking, effective proximity, and degradation efficiency.

DBCO-S-S-PEG3-biotin

Structure of 1430408-09-5

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Category
PROTAC Linker
Molecular Formula
C₄₂H₅₆N₆O₈S₃
Molecular Weight
869.12
Appearance
Transparent Liquid

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

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Purity
>99%
Solubility
In DMSO: 100 mg/mL (115.06 mM; Need ultrasonic)
Appearance
Transparent Liquid
Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N-[2-[2-[2-[2-[3-[2-[[4-(2-azatricyclo[10.4.0.04,9]hexadeca-1(16),4,6,8,12,14-hexaen-10-yn-2-yl)-4-oxobutanoyl]amino]ethyldisulfanyl]propanoylamino]ethoxy]ethoxy]ethoxy]ethyl]pentanamide
Synonyms
Azadibenzocyclooctyne-S-S-PEG3-biotin conjugate
Boiling Point
1194.2±65.0 °C at 760 mmHg
Density
1.3±0.1 g/cm3
InChI Key
ZJVGOGQIAYMKAS-MZOCQUDTSA-N
InChI
InChI=1S/C42H56N6O8S3/c49-37(12-6-5-11-36-41-34(30-57-36)46-42(53)47-41)43-18-21-54-23-25-56-26-24-55-22-19-44-39(51)17-27-58-59-28-20-45-38(50)15-16-40(52)48-29-33-9-2-1-7-31(33)13-14-32-8-3-4-10-35(32)48/h1-4,7-10,34,36,41H,5-6,11-12,15-30H2,(H,43,49)(H,44,51)(H,45,50)(H2,46,47,53)/t34-,36-,41-/m0/s1
SMILES
C1C2C(C(S1)CCCCC(=O)NCCOCCOCCOCCNC(=O)CCSSCCNC(=O)CCC(=O)N3CC4=CC=CC=C4C#CC5=CC=CC=C53)NC(=O)N2
ConcentrationVolumeMass1 mg5 mg10 mg
1 mM1.1506 mL5.7529 mL11.5059 mL
5 mM0.2301 mL1.1506 mL2.3012 mL
10 mM0.1151 mL0.5753 mL1.1506 mL

This DBCO-S-S-PEG3-biotin linker is designed for modular PROTAC and related targeted-degradation workflows where efficient conjugation and reliable handle chemistry are required. It combines a strained cyclooctyne (DBCO) for rapid bioorthogonal coupling with a redox-sensitive disulfide core and a hydrophilic PEG spacer to support solubility and favorable linker presentation. Its biotin functionality enables orthogonal capture or enrichment strategies commonly used in experimental characterization. Detailed structural and reactivity considerations are provided below.

Structure: The linker contains a DBCO moiety for strain-promoted cycloaddition, a disulfide (S–S) linkage that can be cleaved under reducing conditions, and a PEG-based spacer that increases hydrophilicity. A thioether and a biotin substituent provide additional conjugation and affinity functionality, respectively.

Reactivity: DBCO groups typically undergo strain-promoted azide–alkyne cycloaddition with azide-bearing partners without added catalysts, enabling mild, aqueous-compatible coupling. The disulfide segment supports redox-responsive behavior, which can be leveraged to modulate stability and intracellular release in degradation studies. Conjugations are commonly performed in buffered aqueous media; the disulfide’s integrity should be considered when selecting reducing or strongly nucleophilic conditions.

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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:
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
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