Sulfo-SDAD

 CAS No.: 1226983-32-9  Cat No.: BP-502165  Purity: ≥ 90% 4.5  

Sulfo-SDAD is a water-soluble, cleavable heterobifunctional photo-crosslinker containing a sulfo-NHS ester, a 3-methyldiazirine group, and an internal disulfide bond. Structurally, the sulfo-NHS ester enables coupling to primary amines, the diazirine enables UV-activated covalent capture of nearby interaction partners, and the internal disulfide provides a reductively cleavable linkage for downstream analysis. In targeted protein degradation workflows, such linkers are critical because they govern formation of the ternary complex between the degrader, the E3 ligase, and the target protein, influencing both cooperativity and degradation efficiency. As a research-grade component, Sulfo-SDAD is valuable for systematic PROTAC optimization, enabling researchers to explore linker length and polarity effects on binding geometry, cellular uptake, and degradation potency in vitro and in cell-based assays.

Sulfo-SDAD

Structure of 1226983-32-9

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Category
PROTAC Linker
Molecular Formula
C14H19N4NaO8S3
Molecular Weight
490.51
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Powder

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

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Purity
≥ 90%
Appearance
Powder
IUPACName
sodium;1-[3-[2-[3-(3-methyldiazirin-3-yl)propanoylamino]ethyldisulfanyl]propanoyloxy]-2,5-dioxopyrrolidine-3-sulfonate
Synonyms
Sulfo-SDAD(Sulfo-NHS-SS-Diazirine) (sulfosuccinimidyl 2-[(4,4'-azipentanamido)ethyl]-1,3'-dithiopropionate]
Density
1.5±0.1 g/cm3
InChI Key
BTBHSSBEJHAIAF-UHFFFAOYSA-M
InChI
InChI=1S/C14H20N4O8S3.Na/c1-14(16-17-14)4-2-10(19)15-5-7-28-27-6-3-12(21)26-18-11(20)8-9(13(18)22)29(23,24)25;/h9H,2-8H2,1H3,(H,15,19)(H,23,24,25);/q;+1/p-1
SMILES
CC1(N=N1)CCC(=O)NCCSSCCC(=O)ON2C(=O)CC(C2=O)S(=O)(=O)[O-].[Na+]

Sulfo-SDAD is a sulfonated, cleavable linker designed for constructing PROTACs that require controlled spatial presentation between a target-binding ligand and an E3 ligase recruiter. Its anionic sulfonate handle supports aqueous compatibility and can improve handling in linker–ligand coupling workflows. In PROTAC technology, such linkers help tune effective ternary complex formation and degradation potency. The following points describe its structure and practical reactivity considerations in PROTAC assembly.

Structure: Sulfo-SDAD contains a sulfonate functionality that imparts strong polarity and water affinity, alongside a cleavable linker motif suitable for modular synthesis. The molecule features stable covalent linkages that preserve integrity during coupling, while the cleavable region enables downstream activation or controlled release under appropriate conditions.

Reactivity: For PROTAC construction, Sulfo-SDAD is typically used in linker–ligand conjugation steps that rely on chemoselective coupling to complementary functional groups on the warhead and E3-binding moieties. Reaction conditions are commonly optimized for aqueous or mixed-solvent compatibility, using standard coupling strategies and bases, while maintaining mild temperatures to preserve linker stability. Mechanistically, the sulfonate group supports solubility and can influence ion-pairing and effective reaction rates during assembly.

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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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